Besser v. Walsh Phillips v. Artus Portalatin v. Graham Morris v. Artus ( 2010 )


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  •      05-4375-pr; 06-3550-pr; 07-1599-pr; 07-3588-pr; 07-3949-pr
    Besser v. Walsh; Phillips v. Artus; Portalatin v. Graham; Morris v. Artus;
    Washington v. Poole
    1                           UNITED STATES COURT OF APPEALS
    2                               FOR THE SECOND CIRCUIT
    3                                 AUGUST TERM, 2007
    4    (Argued in Tandem: April 16, 2008                Decided: March 31, 2010)
    5      Docket Nos. 05-4375-pr, 06-3550-pr, 07-1599-pr, 07-3588-pr,
    6                               07-3949-pr
    7                     (consolidated for disposition)
    8   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
    9
    10   JAMES BESSER, a/k/a JAMES ZERILLI,
    11             Petitioner-Appellant,
    12
    13               v.                                              No. 05-4375-pr
    14
    15   JAMES WALSH, Superintendent, Sullivan Correctional Facility,
    16             Respondent-Appellee.
    17
    18   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
    19
    20   WILLIAM PHILLIPS,
    21             Petitioner-Appellant,
    22
    23                v.                                             No. 06-3550-pr
    24
    25   DALE ARTUS, Superintendent, Clinton Correctional Facility,
    26   and ANDREW M. CUOMO, New York State Attorney General,*
    27             Respondents-Appellees.
    28
    29   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
    30
    31   CARLOS PORTALATIN,
    32             Petitioner-Appellee,
    33
    34                     v.                                        No. 07-1599-pr
    35
    36   HAROLD GRAHAM, Superintendent, Auburn Correctional Facility,
    37             Respondent-Appellant.
    38
    39   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
    *
    Pursuant to Federal Rule of Appellate Procedure 43(c)(2),
    Andrew M. Cuomo, New York State Attorney General, is
    automatically substituted as respondent-appellee for Elliot L.
    Spitzer, former New York State Attorney General.
    1
    1   VANCE MORRIS,
    2             Petitioner-Appellant,
    3
    4                      v.                                 No. 07-3588-pr
    5
    6   DALE ARTUS, Superintendent, Clinton Correctional Facility, and
    7   ANDREW M. CUOMO, New York State Attorney General,**
    8             Respondents-Appellees.
    9
    10   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
    11
    12   WILLIAM WASHINGTON,
    13             Petitioner-Appellee,
    14
    15                v.                                       No. 07-3949-pr
    16
    17   THOMAS POOLE, Superintendent, Five Points Correctional Facility,
    18             Respondent-Appellant.***
    19
    20   - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
    21
    22   B e f o r e:      WINTER, SACK, Circuit Judges and MURTHA, District
    23   Judge.****
    24        Five New York prisoners, sentenced under New York’s
    25   persistent offender statute, petitioned for a writ of habeas
    26   corpus.      We hold principally that the New York courts’ upholding
    27   of the constitutionality of the New York state persistent felony
    28   offender statute after the United States Supreme Court’s decision
    29   in Blakely v. Washington, 
    542 U.S. 296
     (2004), was an
    30   unreasonable application of clearly established Sixth and
    **
    Pursuant to Federal Rule of Appellate Procedure 43(c)(2),
    Andrew M. Cuomo, New York State Attorney General, is
    automatically substituted as respondent-appellee for Elliot L.
    Spitzer, former New York State Attorney General.
    ***
    The Clerk of the Court is directed to amend the official
    caption in these cases to conform to the listing of the parties
    above.
    ****
    The Honorable J. Garvan Murtha, United States District
    Judge for the District of Vermont, sitting by designation.
    2
    1   Fourteenth Amendment law.
    2                               RICHARD M. GREENBERG, Office of the
    3                               Appellate Defender, New York, New York,
    4                               for Petitioner-Appellant Besser.
    5
    6                               MARTIN M. LUCENTE, The Legal Aid
    7                               Society, Criminal Appeals Bureau, New
    8                               York, New York, for Petitioner-Appellant
    9                               Phillips.
    10
    11                               JOSHUA MICHAEL LEVINE (Lynne W.L.
    12                               Fahey), Appellate Advocates, New York,
    13                               New York, for Petitioner-Appellee
    14                               Portalatin.
    15
    16                               ANDREW C. FINE (Paul Wiener), The Legal
    17                               Aid Society, Criminal Appeals Bureau,
    18                               New York, New York, for Petitioner-
    19                               Appellant Morris.
    20
    21                               JONATHAN M. KIRSHBAUM (Robert S. Dean),
    22                               Center For Appellate Litigation, New
    23                               York, New York, for Petitioner-Appellee
    24                               Washington.
    25
    26                               MARK DWYER, Assistant District Attorney,
    27                               of counsel (Robert M. Morgenthau,
    28                               District Attorney, New York County;
    29                               Morrie I. Kleinbart, Special Assistant
    30                               District Attorney; Nicole Beder,
    31                               Assistant District Attorney, of
    32                               counsel), New York, New York, for
    33                               Respondent-Appellee Walsh.
    34
    35                               ROSEANN B. MACKECHNIE, Deputy Solicitor
    36                               General for Criminal Matters (Andrew M.
    37                               Cuomo, Attorney General of the State of
    38                               New York; Barbara D. Underwood,
    39                               Solicitor General; Malancha Chanda,
    40                               Assistant Attorney General, of counsel),
    41                               New York, New York, for Respondents-
    42                               Appellees Artus and Cuomo.
    43
    44                               LEONARD JOBLOVE, Assistant District
    45                               Attorney, of counsel (Charles J. Hynes,
    46                               District Attorney, Kings County; Ann
    47                               Bordley, Assistant District Attorney, of
    48                               counsel), Brooklyn, New York, for
    49                               Respondent-Appellant Graham.
    50
    51
    3
    1                             Andrew M. Cuomo, Attorney General of the
    2                             State of New York (Barbara D. Underwood,
    3                             Solicitor General; Roseann B.
    4                             MacKechnie, Deputy Solicitor General for
    5                             Criminal Matters; Malancha Chanda,
    6                             Assistant Attorney General, of counsel),
    7                             New York, New York, for Respondent-
    8                             Appellant Poole.
    9
    10                             Marshall A. Mintz, Mintz & Oppenheim
    11                             LLP, New York, New York (Richard D.
    12                             Willstatter, Chair of the Amicus Curiae
    13                             Committee of the New York State
    14                             Association of Criminal Defense Lawyers,
    15                             Vice-Chair of the 2nd Circuit Amicus
    16                             Curiae Committee of the National
    17                             Association of Criminal Defense Lawyers,
    18                             White Plains, New York), for Amici
    19                             Curiae New York State Association of
    20                             Criminal Defense Lawyers and National
    21                             Association of Criminal Defense Lawyers.
    22
    23   WINTER, Circuit Judge:
    24        The principal question on appeal is whether New York state
    25   court decisions affirming sentences enhanced under New York’s
    26   persistent felony offender (“PFO”) statute, 
    N.Y. Penal Law § 27
       70.10, unreasonably applied clearly established federal law.    28
    
    28 U.S.C. § 2254
    (d).
    29        The district court issued a writ of habeas corpus in the
    30   petitions of Carlos Portalatin and William Washington and the
    31   relevant state authorities brought this appeal.1   See Washington
    32   v. Poole, 
    507 F. Supp. 2d 342
    , 344 (S.D.N.Y. 2007) (Koeltl, J.);
    33   Portalatin v. Graham, 
    478 F. Supp. 2d 385
    , 386 (E.D.N.Y. 2007)
    34   (Gleeson, J.).   The district court declined to issue the writ in
    35   the petitions of James Besser, William Phillips, and Vance
    36   Morris, who then appealed.   See Morris v. Artus, No. 06 Civ.
    37   4095(RKS), 
    2007 WL 2200699
    , at *1 (S.D.N.Y. July 30, 2007)
    4
    1   (Sweet, J.); Phillips v. Artus, No. 05 Civ. 7974(PAC), 
    2006 WL 2
       1867386, at *1 (S.D.N.Y. June 30, 2006) (Crotty, J.); Besser v.
    3   Walsh, No. 02 Civ. 6775(LAK), 
    2005 WL 1489141
    , at *1 (S.D.N.Y.
    4   June 22, 2005) (Kaplan, J.).   Because these five appeals
    5   presented substantially similar or overlapping issues, we heard
    6   them together.
    7        We hold that the Sixth Amendment right to a jury trial,
    8   applicable to the states as incorporated by the Fourteenth
    9   Amendment, prohibits the type of judicial fact-finding resulting
    10   in enhanced sentences under New York’s PFO statute.   We also hold
    11   that this prohibition was not clearly established until Blakely
    12   v. Washington, 
    542 U.S. 296
     (2004).   Because Besser’s conviction
    13   became final before Blakely issued, the state court decisions
    14   upholding his conviction were neither contrary to nor an
    15   unreasonable application of clearly established federal law.    We
    16   therefore affirm the denial of the writ as to Besser.   However,
    17   because the relevant state court decisions upholding enhanced
    18   sentences for Phillips, Morris, Portalatin, and Washington were
    19   issued after Blakely, those decisions were not reasonable
    20   applications of clearly established law.    Nevertheless, we remand
    21   these cases to the district court for a determination of whether
    22   the error was harmless.
    23                              BACKGROUND
    24   a) The Persistent Felony Offender Statute
    25        There are three increasingly harsh levels of sentencing
    26   applicable to felony offenders under Article 70 of New York’s
    5
    1   penal laws pertinent to this appeal.     First-time felony offenders
    2   are generally sentenced according to indeterminate ranges based
    3   on the class of offense.    See 
    N.Y. Penal Law § 70.00.2
        Second
    4   felony offenders are subject to enhanced sentences, based solely
    5   upon the finding of one qualifying prior felony conviction, again
    6   according to the class of offense.     See 
    id.
     § 70.06.    Under the
    7   PFO statute, a defendant who has been previously convicted of two
    8   felonies is a “persistent felony offender” (sometimes “PFO”).
    9   See id. § 70.10(1)(a).     PFO’s may be sentenced to an
    10   indeterminate sentence in the range authorized for Class A-I
    11   felony offenders rather than the range authorized for the class
    12   of the defendant’s actual offense.     See id. § 70.10(2);3 see also
    13   
    N.Y. Crim. Proc. Law § 400.20
    (1)(b).     Class A-I felonies carry a
    14   minimum sentence of 15 years and a maximum of life.4      See N.Y.
    15   Penal Law §§ 70.00(2)(a), 70.00(3)(a)(i).5
    16        The difference in a defendant’s sentencing exposure depends
    17   heavily upon which level’s range is applicable.     Once classified
    18   as a PFO, a defendant may be subject to a minimum sentence
    19   exceeding the maximum sentence for second felony offenders
    20   applicable to the crime committed.     For example, a first-time
    21   offender convicted of a Class E felony would be subject to a term
    22   of 1 1/3 to 4 years.   See id. § 70.00(2)-(3).    Were the defendant
    23   sentenced for a Class E felony as a second felony offender, he or
    24   she would be subject to a term of 1.5 to 4 years.     See id. §
    25   70.06(3)-(4).   The same defendant given the enhanced sentence
    6
    1   under the PFO statute would be subject to a term of 15 years to
    2   life.    See id. §§ 70.00(2)-(3), 70.10(2).
    3           Under the provisions applicable to first and second felony
    4   offenders, the existence or non-existence of a prior felony alone
    5   determines the applicable range.       See id. §§ 70.00-70.06.   To
    6   sentence under the PFO statute, the sentencing court must make a
    7   finding of at least two prior felony convictions, rendering that
    8   defendant a PFO and exposing him or her to a Class A-I sentence.
    9   See id. § 70.10.     After making that finding, the court turns to
    10   whether “the history and character of the defendant and the
    11   nature and circumstances of his criminal conduct” (sometimes
    12   “history/character/criminal conduct”), id. § 70.10(2); N.Y. Crim.
    13   Proc. Law § 400.20(1), is such that the PFO should, in the public
    14   interest, be given a Class A-I sentence.6      
    N.Y. Crim. Proc. Law § 15
       400.20(1).    In making this finding, the court must conduct a
    16   hearing at which the prosecution bears the burden of proof and
    17   “[m]atters pertaining to the defendant’s history and character
    18   and the nature and circumstances of his criminal conduct” must be
    19   established by a preponderance of the evidence.      
    Id.
     § 400.20(5).
    20   “Uncontroverted allegations in the statement of the court are
    21   deemed evidence in the record.”    Id. § 400.20(7).
    22           If the sentencing court imposes a Class A-I sentence, “the
    23   reasons for the court’s opinion shall be set forth in the
    24   record.”    
    N.Y. Penal Law § 70.10
    (2).    The imposition of that
    25   enhanced sentence is then subject to two kinds of appellate
    26   review.    First, an appellate court has the power, in the
    7
    1   “interest[s] of justice,” to reduce a Class A-I sentence within
    2   the Class A-I range, e.g., from 19 years to life to 15 years to
    3   life.    See 
    N.Y. Crim. Proc. Law § 470.20
    (6).   Second, an
    4   imposition of a Class A-I sentence is subject to an “interest[s]
    5   of justice” review and will be “held erroneous as a matter of
    6   law, [if] the sentencing court acts arbitrarily or irrationally.”
    7   People v. Rivera, 
    833 N.E.2d 194
    , 199 (N.Y. 2005).     Were
    8   imposition of a Class A-I sentence under the PFO statute found by
    9   an appellate court to be “arbitrary[]” or “irrational[,]” the
    10   court must resentence the defendant or remand for resentencing to
    11   a “legally authorized lesser sentence,” 
    N.Y. Crim. Proc. Law § 12
       470.20; see also People v. LaSalle, 
    734 N.E.2d 749
    , 750 (N.Y.
    13   2000) (memorandum decision), usually as a second felony offender
    14   or second violent felony offender.     See, e.g., People v.
    
    15 Williams, 658
     N.Y.S.2d 264, 265 (App. Div. 1997); see also People
    16   v. Greene, 
    871 N.Y.S.2d 323
    , 325 (App. Div. 2008) (citing
    
    17 Williams, 658
     N.Y.S.2d at 265); People v. Truesdale, 
    845 N.Y.S.2d 18
       363, 364-65 (App. Div. 2007); cf. People v. Wilsey, 
    753 N.Y.S.2d 19
       232, 233 (App. Div. 2003); People v. Yale, 
    373 N.Y.S.2d 901
    , 904-
    20   06 (App. Div. 1975).
    21           Because second felony offender status usually exposes a
    22   defendant to maximum sentences below the maximum (and often the
    23   minimum) of the Class A-I range, serious constitutional issues
    24   arise, as discussed infra, and our interpretation of the PFO
    25   statute is critical to the constitutional analysis.    In the
    26   briefs submitted by state authorities, it was suggested that a
    8
    1   finding of two felony convictions alone locks in the Class A-I
    2   range, with life as a maximum.    We disagree.   The
    3   history/character/criminal conduct findings, which are subject to
    4   appellate review, are necessary to lock in the Class A-I range
    5   and, if such findings do not justify a Class A-I sentence,
    6   require the sentencing court to sentence the defendant in a
    7   lesser range, usually as a second felony (or violent felony)
    8   offender.7
    9        The state authorities rely for their argument upon language
    10   in Rivera.    We therefore quote the pertinent portion of that
    11   decision at length:
    12                     [D]efendants are eligible for persistent
    13                felony offender sentencing based solely on
    14                whether they had two prior felony
    15                convictions. Thus, . . . no further findings
    16                are required. This conclusion takes
    17                defendant’s sentence outside the scope of the
    18                violations described in Apprendi and its
    19                progeny.
    20
    21                     The [United States] Supreme Court has
    22                held that a judge (as opposed to a jury) may
    23                find the fact of a defendant’s prior
    24                conviction without violating the Sixth
    25                Amendment . . . .
    26
    27                     After determining defendant’s status as
    28                a persistent felony offender, the [court that
    29                sentenced Rivera] went on to consider other
    30                facts in weighing whether to impose the
    31                authorized persistent felony offender
    32                sentence. . . . If, based on all it heard,
    33                the [sentencing] court’s view of the facts
    34                surrounding defendant’s history and character
    35                were different, the court might well have
    36                exercised its discretion to impose a less
    37                severe sentence.
    38
    39                     Nevertheless, the relevant question
    40                under the United States Constitution is not
    41                whether those facts were essential to the
    9
    1             trial court’s opinion ([N.Y. Crim. Proc. Law
    2             §] 400.20[1][b]), but whether there are any
    3             facts other than the predicate convictions
    4             that must be found to make recidivist
    5             sentencing possible (see Blakely, 
    542 U.S. at
    6             302-303 . . .). Our answer is no. . . .
    7
    8                  . . . .
    9
    10                  To reiterate our analysis . . . , a
    11             defendant adjudicated as a persistent felony
    12             offender has a statutory right to present
    13             evidence that might influence the court to
    14             exercise its discretion to hand down a
    15             sentence as if no recidivism finding existed,
    16             while the People retain the burden to show
    17             that the defendant deserves the higher
    18             sentence. Nevertheless, once a defendant is
    19             adjudged a persistent felony offender, a
    20             recidivism sentence cannot be held erroneous
    21             as a matter of law, unless the sentencing
    22             court acts arbitrarily or irrationally.
    23
    24                  The court’s opinion is, of course,
    25             subject to appellate review, as is any
    26             exercise of discretion. The Appellate
    27             Division, in its own discretion, may conclude
    28             that a persistent felony offender sentence is
    29             too harsh or otherwise improvident. . . . A
    30             determination of that kind, however, is based
    31             not on the law but as an exercise of the
    32             Appellate Division’s discretion in the
    33             interest of justice as reserved uniquely to
    34             that Court ([N.Y. Crim. Proc. Law §] 470.20
    35             [6]).7
    36
    7
    37                    See e.g., People v. Williams, 239
    
    38 A.D.2d 269
    , 269-270, 
    658 N.Y.S.2d 264
     (1st
    39             Dept 1997) (reducing a persistent felony
    40             offender sentence in the interest of justice,
    41             based on defendant’s rehabilitation) . . . .
    42
    43   Rivera, 833 N.E.2d at 198-99.
    44        While Rivera states that two prior convictions alone render
    45   a defendant “eligible for,” or “subject to,” a Class A-I sentence
    46   -- or make such a sentence “possible” -- it follows the language
    47   of the PFO statute in giving a sentencing court discretion to
    10
    1   impose such a sentence but only if the court finds that “the
    2   history and character of the defendant and the nature and
    3   circumstances of [defendant’s] criminal conduct indicate that
    4   extended incarceration and life-time supervision will best serve
    5   the public interest . . . .”    
    N.Y. Penal Law § 70.10
    ; Rivera, 833
    6   N.E.2d at 197-98.    Rivera, therefore, confirms that, while a
    7   defendant with two or more felony convictions is, by virtue of
    8   that fact alone, “eligible for” and “subject to” a Class A-I
    9   sentence, a sentencing court may not impose a Class A-I sentence
    10   unless it has found that the history/character/criminal conduct
    11   factors justify that enhanced sentence.   See Rivera, 
    833 N.E.2d 12
       at 198-99.    As Rivera stated, these factors govern “whether to
    13   impose the authorized persistent offender sentence” or whether
    14   “to hand down a sentence as if no recidivism finding existed.”
    15   
    Id.
       Further, Rivera cited as an example of the proper procedure
    16   People v. Williams, 
    658 N.Y.S.2d 264
    , a decision that found a
    17   Class A-I sentence to be “an improvident exercise of discretion”
    18   and ordered the resentencing of the defendant “as a second felony
    19   offender.”    Williams, 
    658 N.Y.S.2d at 265
    ; see Rivera, 
    833 N.E.2d 20
       at 199 n.7.
    21         Therefore, it is clear from the statute and from Rivera
    22   that, absent findings beyond the existence of two or more felony
    23   convictions, the Class A-I range may not be imposed, and a
    24   defendant must be sentenced within a lesser range, usually as a
    25   second felony offender.   (Of course, the criminal history may in
    26   some cases be sufficient to support such findings.)   It is also
    11
    1   clear that a Class A-I sentence usually has a statutory maximum
    2   above the statutory maximum for second felony offenders.    Compare
    3   
    N.Y. Penal Law §§ 70.04
    (3), 70.06(3), with 
    id.
     § 70.00(2)(a).
    4        The New York Court of Appeals has repeatedly rejected Sixth
    5   Amendment challenges to the sentencing scheme.   See People v.
    6   Quinones, 
    906 N.E.2d 1033
    , 1034 (N.Y. 2009); Rivera, 
    833 N.E.2d 7
       at 195; People v. Rosen, 
    752 N.E.2d 844
    , 846 (N.Y. 2001).     Before
    8   Blakely and Cunningham v. California, 
    127 S. Ct. 856
     (2007), we
    9   twice held that Rosen did not unreasonably apply either Apprendi
    10   v. New Jersey, 
    530 U.S. 466
     (2000), or the Supreme Court’s later
    11   decision in Ring v. Arizona, 
    536 U.S. 584
     (2002).    See Brown v.
    12   Miller (“Brown II”), 
    451 F.3d 54
    , 56-57 (2d Cir. 2006)
    13   (addressing both Apprendi and Ring); Brown v. Greiner (“Brown
    14   I”), 
    409 F.3d 523
    , 526 (2d Cir. 2005) (addressing Apprendi).
    15   But, as discussed infra, neither Brown decision addresses the
    16   effect of the Supreme Court’s more recent decisions in Blakely
    17   and Cunningham.
    18   b) Prior State Court and Federal Proceedings Concerning the
    19   Petitions
    20        1) James Besser
    21        Besser was convicted, following a jury trial, of one count
    22   of enterprise corruption, a Class B felony, in violation of New
    23   York Penal Law § 460.20.   The jury found that he had committed
    24   three predicate criminal acts with the intent to participate in
    25   the affairs of the Colombo Organized Crime Family.
    12
    1         New York moved to have Besser sentenced as a Class A-I
    2   offender pursuant to the PFO statute.   Counsel for Besser
    3   registered objections to, inter alia, substantial portions of the
    4   state’s statement of alleged facts regarding his history and
    5   character and its supporting exhibits, which included court and
    6   police records.
    7         The court found the predicate felony convictions qualified
    8   Besser for sentencing pursuant to the PFO statute.   The judge
    9   then reviewed the evidence submitted by the state that included
    10   information relating to Besser’s uncharged murder attempts and to
    11   a brutal beating for which charges were then pending.   It
    12   concluded that Besser’s “history and character warrant[ed] a
    13   sentence of extended incarceration and lifetime supervision . . .
    14   .”   Besser received a sentence under the PFO statute of 15 years
    15   to life imprisonment.    Had Besser been sentenced as a second
    16   felony offender, he would have been subject to a sentence of a
    17   minimum of 4.5 years to a maximum of 25 years.   See N.Y. Penal
    18   Law § 70.06(3)-(4).
    19         Besser appealed, challenging, inter alia, his sentence as
    20   imposed in violation of his Sixth Amendment rights under
    21   Apprendi.    On May 1, 2001, the New York Court of Appeals rejected
    22   that challenge, stating that because Besser had failed to raise
    23   the Apprendi claim before the sentencing court, the issue was not
    24   preserved.   See People v. Besser, 
    749 N.E.2d 727
    , 733 (N.Y. 2001)
    25   (citing Rosen, 
    752 N.E.2d 844
    ).
    13
    1        On August 26, 2002, Besser filed the present petition in the
    2   Southern District.   Judge Kaplan denied the petition, based on
    3   our decision in Brown I, 
    409 F.3d 523
    , but “grant[ed] a
    4   certificate of appealability on the question whether New York’s
    5   [PFO] statute violates the rule of Apprendi . . . .”    See Besser
    6   v. Walsh, 
    2005 WL 1489141
    , at *1.
    7        2) Vance Morris
    8        Morris was convicted by a jury, of sixteen counts of first
    9   degree criminal contempt, a Class E felony.   See 
    N.Y. Penal Law § 10
       215.51(b).   The conviction was based on two telephone threats
    11   against his girlfriend in violation of four separate orders of
    12   protection issued as a result of repeated violent acts and
    13   general mayhem at his girlfriend’s apartment and in her
    14   community.   The state moved to sentence Morris as a Class A-I
    15   offender under the PFO statute.    Morris conceded several prior
    16   felony convictions for attempted robbery, robbery, grand larceny,
    17   and possession of a controlled substance, but disputed whether
    18   his criminal conduct, history and character warranted an enhanced
    19   sentence.    At the sentencing hearing on July 24, 2002, the court
    20   first determined Morris to be a PFO based on three qualifying
    21   prior felony convictions.   The court then examined the evidence
    22   regarding Morris’s history and character.   Noting the state’s
    23   evidence regarding the defendant’s “relevant criminal conduct,
    24   his bad acts, uncontrollable [rage], defiance of authority and
    25   hostile conduct toward women,” the court sentenced Morris to
    26   sixteen concurrent indeterminate terms of 15 years to life
    14
    1   imprisonment.   Had Morris been sentenced as a second felony
    2   offender for any of these counts, he would have been subject to a
    3   minimum of 1.5 years and a maximum of 4 years.     See N.Y. Penal
    4   Law § 70.06(3)-(4).
    5        On appeal, Morris raised several issues, including, for the
    6   first time, an Apprendi challenge to his sentence.     On August 4,
    7   2005, the Appellate Division unanimously affirmed, stating that
    8   even if Morris had preserved the Apprendi challenge, it would be
    9   rejected.   See People v. Morris, 
    800 N.Y.S.2d 6
    , 7 (App. Div.
    10   2005) (citing Rivera, 
    833 N.E.2d 194
    , and Rosen,
    752 N.E.2d 844
    ).
    11   On September 27, 2005, the New York Court of Appeals summarily
    12   denied Morris leave to appeal.   People v. Morris, 
    837 N.E.2d 744
    13   (N.Y. 2005).
    14        Morris subsequently petitioned for a writ of habeas corpus
    15   pursuant to 
    28 U.S.C. § 2254
    .    Relying on Brown I, 
    409 F.3d 523
    ,
    16   and Brown II, 
    451 F.3d 54
    , as well as Rivera, 
    833 N.E.2d 194
    ,
    17   Judge Sweet denied the petition.      Morris v. Artus, 
    2007 WL 18
       2200699, at *8-*10.   Morris then brought this appeal.
    19        3) William Phillips
    20        Phillips was convicted by a jury of second degree robbery of
    21   a candy and newspaper store, a Class C violent felony offense at
    22   that time,8 in violation of New York Penal Law § 160.10(1).      The
    23   state moved to have Phillips sentenced as a Class A-I offender.
    24   At the sentencing hearing, Phillips did not deny his six prior
    25   felony convictions, nor did he raise any constitutional challenge
    26   to the PFO statute or his prior convictions.     Phillips did,
    15
    1   however, contest whether his criminal conduct, history, and
    2   character was of the kind warranting an enhanced sentence.     The
    3   court found that in light of Phillips’s failure to take advantage
    4   of “favorable plea bargains, minimal sentences, early parole, a
    5   temporary release program, community service in lieu of
    6   incarceration and a drug program,” he had shown “time and again,
    7   throughout his entire adult life, that he cannot be trusted to
    8   function normally in society and that he is unwilling and unable
    9   to rehabilitate himself.”   Phillips was sentenced to a term of 16
    10   years to life in prison.    If Phillips had not been sentenced
    11   pursuant to the PFO statute, he would have been sentenced as a
    12   second violent felony offender because of a 1987 guilty plea for
    13   attempted robbery in the second degree, a Class D violent felony
    14   offense at that time.   See 
    N.Y. Penal Law §§ 70.02
    (1), 70.04(1).
    15   Had he been sentenced as a second violent felony offender, he
    16   would have been subject to a determinate sentence, with a minimum
    17   of 7 years and a maximum of 15 years.   See 
    N.Y. Penal Law § 18
       70.04(3)(b).
    19        In a collateral proceeding brought pursuant to New York
    20   Criminal Procedure Law § 440.20, Phillips raised for the first
    21   time an Apprendi challenge to his sentence.    On June 25, 2003,
    22   the court rejected his claim on the merits.
    23        Thereafter, Phillips appealed both his conviction and the
    24   denial of his Section 440.20 motion.    On December 18, 2003, the
    25   Appellate Division unanimously affirmed the underlying conviction
    26   and the denial of the Section 440.20 motion, concluding that “the
    16
    1   particular facts upon which the sentencing court based its
    2   determination were all permissible under Apprendi . . . .”
    3   People v. Phillips, 
    768 N.Y.S.2d 812
    , 812 (App. Div. 2003).      The
    4   New York Court of Appeals denied Phillips leave to appeal without
    5   prejudice to renewal, and then, on September 30, 2004, denied
    6   leave again upon reconsideration.      People v. Phillips, 
    816 N.E.2d 7
       207 (N.Y. 2004), on reconsideration, 
    818 N.E.2d 680
     (N.Y. 2004).
    8        Phillips then brought the instant petition in the Southern
    9   District for a writ of habeas corpus.      On June 30, 2006, Judge
    10   Crotty rejected Phillips’s Apprendi challenge, relying on Brown
    11   I, 
    409 F.3d 523
    , and Brown II, 
    451 F.3d 54
    .      Phillips v. Artus,
    12   
    2006 WL 1867386
    , at *5-*7.    The court declined to issue a
    13   certificate of appealability.     
    Id. at *7
    .   Phillips then moved
    14   for a certificate of appealability in this court, which was
    15   granted.9
    16        4) Carlos Portalatin
    17        Portalatin was found guilty by a jury of one count each of
    18   second degree kidnapping and first degree robbery in connection
    19   with a carjacking incident.    See 
    N.Y. Penal Law §§ 135.20
    ,
    20   160.15.     Both of these offenses are Class B violent felony
    21   offenses.    See 
    N.Y. Penal Law § 70.02
    (1).    The state moved to
    22   sentence Portalatin as a Class A-I.      At the sentencing hearing on
    23   April 28, 2003, the trial court adjudicated Portalatin a PFO,
    24   citing two prior convictions.    Portalatin contended that his
    25   criminal conduct, history, and character were not of the kind to
    26   warrant an enhanced sentence.     As to his history and character,
    17
    1   the court noted that “looking back on the history of this
    2   defendant, and having read these reports, it is clear that there
    3   is very little in his experience or his life that would support
    4   the story he gave on the witness stand . . . .”     In light of
    5   Portalatin’s repeated parole revocations, disinclination to
    6   accept drug treatment, repeated drug charges, “inclination to
    7   prey upon others,” his inability to “control his own problems,”
    8   the fact that a carjacking is a “truly terrifying experience,”
    9   and his displaying what appeared to be a firearm during the
    10   crime, the court imposed two concurrent terms of 18 years to life
    11   imprisonment.    If Portalatin had not been sentenced as a PFO, he
    12   would have been sentenced as a second violent felony offender due
    13   to a previous conviction in 1995 for attempted burglary in the
    14   second degree, a Class D violent felony offense.    See N.Y. Penal
    15   Law §§ 70.02(1), 70.04(1).     As a second violent felony offender,
    16   Portalatin would have been subject to a determinate sentence for
    17   each count that was between 10 to 25 years.    See 
    N.Y. Penal Law § 18
       70.04(3)(a).
    19           Portalatin brought an Apprendi challenge to his sentencing
    20   under the PFO statute for the first time in his appeal to the
    21   Appellate Division.     Finding Portalatin’s Apprendi challenge both
    22   unpreserved and without merit, the court affirmed his judgment of
    23   conviction and sentence on May 16, 2005.    People v. Portalatin,
    24   
    795 N.Y.S.2d 334
    , 335 (App. Div. 2005) (citing Rosen, 
    752 N.E.2d 25
       844).    On July 6, 2005, Portalatin’s application for leave to
    18
    1   appeal was denied by the New York Court of Appeals.    People v.
    2   Portalatin, 
    5 N.Y.3d 793
    , 793 (2005).
    3        Portalatin then sought a writ of habeas corpus in the
    4   Eastern District, which Judge Gleeson granted on March 22, 2007.
    5   Portalatin v. Graham, 
    478 F. Supp. 2d at 386
    .    The state then
    6   took this appeal.
    7        5) William Washington
    8        Washington was convicted by a jury of fourth degree grand
    9   larceny, a Class E felony, in connection with his theft of a
    10   wallet at a bus terminal.    See 
    N.Y. Penal Law § 155.30
    .      The
    11   state moved to sentence Washington pursuant to the PFO statute.
    12   Washington’s memorandum in opposition raised constitutional
    13   objections to the PFO statute based on Apprendi, Ring, and Harris
    14   v. United States, 
    536 U.S. 545
     (2002).     At the PFO hearing on
    15   January 23, 2003, Washington conceded two prior felony
    16   convictions.   He also reasserted his Apprendi argument and
    17   contested whether his criminal conduct, history and background
    18   were of the kind to warrant an enhanced sentence.     At the
    19   sentencing hearing on January 30, 2003, the court concluded that
    20   the two unchallenged prior felony convictions triggered the PFO
    21   statute.   With respect to Washington’s criminal conduct, history,
    22   and character, the court noted some fifty-seven arrests outside
    23   of New York and fifteen theft-related misdemeanor and felony
    24   convictions in New York, the defendant’s extensive pattern of
    25   thefts in the same locale, and a history of recidivism placing
    26   him “far beyond any rehabilitation.”     The court then sentenced
    19
    1   Washington to a term of 20 years to life imprisonment.     Had
    2   Washington been sentenced as a second felony offender, he would
    3   have been subject to an indeterminate sentence of a minimum of
    4   1.5 years and a maximum of 4 years.    See 
    N.Y. Penal Law § 5
       70.06(3)-(4).
    6           On August 4, 2005, the Appellate Division upheld the
    7   constitutionality of the PFO sentencing scheme and affirmed
    8   Washington’s adjudication as a persistent felony offender.       See
    9   People v. Washington, 
    799 N.Y.S.2d 217
    , 218 (App. Div. 2005)
    10   (citing Rivera, 
    833 N.E.2d 194
    ; Rosen, 
    752 N.E.2d 844
    ).        The
    11   court nonetheless exercised its discretion to reduce the sentence
    12   in the interest of justice to a Class A-I sentence of 15 years to
    13   life.    See 
    id. at 217-18
    ; see also 
    N.Y. Penal Law § 70.00
    (2)-(3).
    14   Thereafter, the New York Court of Appeals denied leave to appeal,
    15   People v. Washington, 
    5 N.Y.3d 834
     (2005), and on January 9,
    16   2006, the United States Supreme Court denied Washington’s
    17   petition for certiorari.    Washington v. New York, 
    546 U.S. 1104
    18   (2006).    Washington then petitioned in the Southern District for
    19   a writ of habeas corpus, which Judge Koeltl granted on August 28,
    20   2007.     See Washington v. Poole, 
    507 F. Supp. 2d 342
    , 344
    21   (S.D.N.Y. 2007).     The state then brought this appeal.
    22                                 DISCUSSION
    23   a) Standard of Review
    24           We review de novo a decision to grant or deny a petition for
    25   writ of habeas corpus.    Morris v. Reynolds, 
    264 F.3d 38
    , 45 (2d
    26   Cir. 2001).    Under the Antiterrorism and Effective Death Penalty
    20
    1   Act (“AEDPA”), “with respect to any claim that was adjudicated on
    2   the merits in State court proceedings,” a federal court may not
    3   grant habeas relief unless the state court’s resolution of the
    4   claim on the merits:
    5                         (1) resulted in a decision
    6                    that was contrary to, or involved
    7                    an unreasonable application of,
    8                    clearly established Federal law, as
    9                    determined by the Supreme Court of
    10                    the United States; or
    11
    12                         (2) resulted in a decision
    13                    that was based on an unreasonable
    14                    determination of the facts in light
    15                    of the evidence presented in the
    16                    State court proceeding.
    17
    18   
    28 U.S.C. § 2254
    (d).
    19        A state court decision is “contrary to” clearly established
    20   law for AEDPA purposes only if “the state court arrives at a
    21   conclusion opposite to that reached by [the Supreme] Court on a
    22   question of law or if the state court decides a case differently
    23   than [the] Court has on a set of materially indistinguishable
    24   facts.”    Williams v. Taylor, 
    529 U.S. 362
    , 412-13 (2000)
    25   (O’Connor, J., for the Court).   An “unreasonable application” of
    26   clearly established federal law occurs “if [a] state court
    27   ‘correctly identifies the governing legal rule but applies it
    28   unreasonably to the facts of a particular prisoner’s case,’ or
    29   refuses to extend a legal principle that the Supreme Court has
    30   clearly established to a new situation in which it should
    31   govern.”   Hoi Man Yung v. Walker, 
    468 F.3d 169
    , 176 (2d Cir.
    32   2006) (quoting Williams, 
    529 U.S. at 407-08
    ) (citations omitted).
    33   The proper inquiry is not whether a state court’s application of,
    21
    1   or refusal to extend, the governing law was erroneous, but
    2   whether it was “objectively unreasonable,” Williams, 
    529 U.S. at
    3   409-10, “mean[ing] that petitioner must identify some increment
    4   of incorrectness beyond error in order to obtain habeas relief.”
    5   Cotto v. Herbert, 
    331 F.3d 217
    , 248 (2d Cir. 2003) (internal
    6   quotation marks omitted).
    7          Clearly established federal law “refers to the holdings, as
    8   opposed to the dicta, of [Supreme Court] decisions as of the time
    9   of the relevant state-court decision.”    Williams, 
    529 U.S. at
    10   412.   To assess “clearly established” law, federal habeas courts
    11   apply rules of retroactivity that are generally consistent with
    12   those set forth in Teague v. Lane, 
    489 U.S. 288
     (1989).     See
    13   Mungo v. Duncan, 
    393 F.3d 327
    , 333-34 (2d Cir. 2004).     Teague
    14   prohibits the retroactive application of “new” legal rules on
    15   collateral review.    Teague, 
    489 U.S. at 295-96
    ; see also 
    id.
     at
    16   301 (O’Connor, J., concurring).    Under Teague, “a case announces
    17   a new rule if the result was not dictated by precedent existing
    18   at the time the defendant’s conviction became final.”     
    Id.
     at
    19   301.   AEDPA similarly forbids retroactive application of “new”
    20   legal rules.    See McKinney v. Artuz, 
    326 F.3d 87
    , 96 (2d Cir.
    21   2003) (“Clearly established federal law . . . is law that is
    22   ‘dictated by [Supreme Court] precedent existing at the time the
    23   defendant’s conviction became final.’”) (quoting Williams, 529
    24   U.S. at 381 (Stevens, J., concurring)).   However, as explained
    25   infra, the point of reference for determining “clearly
    22
    1   established law” may differ from the reference point used under
    2   Teague to determine whether a legal rule is “new.”
    3        AEDPA deference applies only if a state court has disposed
    4   of a federal claim “on the merits” and “reduce[d] its disposition
    5   to judgment.”   See Sellan v. Kuhlman, 
    261 F.3d 303
    , 312 (2d Cir.
    6   2001).   In the present matter, petitioners’ federal claims were
    7   all disposed “on the merits” by the New York courts.    Phillips’s
    8   federal claim was rejected “on the merits” by the state court’s
    9   conclusion that “the particular facts upon which the sentencing
    10   court based its determination were all permissible under Apprendi
    11   . . . .”   People v. Phillips, 
    768 N.Y.S.2d at 812
    .    The state
    12   court similarly rejected Washington’s claim “on the merits” by
    13   concluding that “[t]he procedure under which defendant was
    14   adjudicated a persistent felony offender is not
    15   unconstitutional.”   People v. Washington, 
    799 N.Y.S.2d at 218
    .
    16        The federal claims raised by Portalatin, Morris, and Besser
    17   were also decided “on the merits” for AEDPA purposes because each
    18   state court cited People v. Rosen in ruling that those claims
    19   were procedurally barred.   See People v. Besser, 749 N.E.2d at
    20   733; People v. Morris, 
    800 N.Y.S.2d at 7
    ; People v. Portalatin,
    21   
    795 N.Y.S.2d at 335
    .   We held in Brown I that the state court in
    22   People v. Rosen could not have invoked state procedural law and
    23   barred Rosen’s Sixth Amendment claim without first having found
    24   that the claim was without merit.    Brown I, 
    409 F.3d at 532
    .     And
    25   we later held in Brown II that a citation to Rosen in holding
    26   that a claim is procedurally barred establishes that the state
    23
    1   court decision was interwoven with federal law.   Brown II, 451
    2   F.3d at 56-57.   Therefore, the procedural rulings in the present
    3   matter are not “adequate” and “independent” grounds for the
    4   decision and do not bar us from addressing the federal claims on
    5   habeas review.   See Brown II, 
    451 F.3d at 56-57
    ; Brown I, 409
    6   F.3d at 532.   We thus proceed with these appeals under AEDPA’s
    7   deferential standard of review.
    8   b) AEDPA Claim and “Clearly Established” Sixth Amendment Law
    9        Our analysis will proceed as follows:   we first address
    10   whether it was objectively unreasonable to uphold petitioners’
    11   Class A-I sentences in light of the Supreme Court decisions
    12   applying Apprendi.   We then turn to whether that law was “clearly
    13   established” at the relevant time for each petitioner.   This
    14   inquiry leads to two further questions:   first, to what period of
    15   time do we look in determining whether a legal rule was “clearly
    16   established” under AEDPA; second, to what extent does AEDPA allow
    17   us to consider Supreme Court cases that postdate the relevant
    18   period selected.
    19        1) The Apprendi Rule
    20        The Sixth and Fourteenth Amendments guarantee that in
    21   federal and state “criminal prosecutions, the accused shall enjoy
    22   the right to a speedy and public trial, by an impartial jury
    23   . . . .”   U.S. Const. amend. VI; Duncan v. Louisiana, 
    391 U.S. 24
       145, 149 (1968) (holding that the Fourteenth Amendment affords
    25   defendants the right to a jury trial in state prosecutions to the
    26   same extent the Sixth Amendment affords this right in federal
    24
    1   prosecutions).   The Supreme Court has concluded that this
    2   guarantee requires that a jury, not a judge, find any facts
    3   (other than the fact of a prior conviction(s)) that may increase
    4   the penalty for a crime beyond the ordinary statutory maximum.
    5   Apprendi v. New Jersey, 
    530 U.S. 466
    , 490 (2000).
    6        In Apprendi, the petitioner was convicted of possession of a
    7   firearm for an unlawful purpose, punishable under New Jersey law
    8   by a term of incarceration of 5 to 10 years.      
    Id. at 468
    .    A
    9   separate hate crime statute, however, authorized an “extended
    10   term” of imprisonment of 10 to 20 years if the trial judge found
    11   that “[t]he defendant in committing the crime acted with a
    12   purpose to intimidate an individual or group of individuals
    13   because of race, color, gender, handicap, religion, sexual
    14   orientation or ethnicity.”     
    Id. at 468-69
     (quoting N.J. Stat.
    15   Ann. § 2C:44-3(e)) (alteration in original).      Having made such a
    16   finding, the trial judge sentenced Apprendi to 12 years
    17   imprisonment.    Id. at 471.   The Supreme Court held that the
    18   enhanced sentence violated the Sixth Amendment, id. at 497,
    19   concluding that other than the fact of a prior conviction, “any
    20   fact that increases the penalty for a crime beyond the prescribed
    21   statutory maximum must be submitted to a jury, and proved beyond
    22   a reasonable doubt,” id. at 490.       The Court emphasized that “the
    23   relevant inquiry is one not of form, but of effect.”      Id. at 494.
    24        On several subsequent occasions, the Supreme Court
    25   elaborated on the reach of Apprendi.       In Ring, the Supreme Court
    26   addressed a capital sentencing scheme that required sentencing
    25
    1   judges to find at least one statutorily-enumerated aggravating
    2   circumstance before imposing the death penalty.   See Ring, 536
    3   U.S. at 592-93.    Absent such a finding and “[b]ased solely on the
    4   jury’s verdict finding . . . [of guilt], the maximum punishment
    5   [Ring] could have received was life imprisonment.”   Id. at 597
    6   (citing 
    Ariz. Rev. Stat. § 13-703
    ).    Ring concluded that this
    7   scheme ran afoul of Apprendi, 
    id. at 609
    , explaining that “[i]f a
    8   State makes an increase in a defendant’s authorized punishment
    9   contingent on the finding of a fact, that fact -- no matter how
    10   the State labels it -- must be found by a jury beyond a
    11   reasonable doubt,” 
    id. at 602
    .
    12        Then came Blakely.    Under Washington state’s Sentencing
    13   Reform Act, judges were ordinarily required to impose a sentence
    14   within a “standard range” that might well be significantly below
    15   the statutory maximum for the underlying offense.    See Blakely,
    16   
    542 U.S. at 299
    .   The charged offense in Blakely’s case, second
    17   degree kidnapping, was a class of felony subject to a maximum
    18   sentence of 10 years.   
    Id.
     (citing 
    Wash. Rev. Code §§ 19
       9A.20.021(1)(b), 9A.40.030(3)).    Other provisions, however,
    20   further limited the range for a defendant in Blakely’s
    21   circumstances to a “standard” sentencing range of 49 to 53
    22   months.   
    Id.
       And yet another provision permitted the sentencing
    23   court to impose a sentence above that “standard” range if it made
    24   factual findings on the record sufficient to support a conclusion
    25   that there were “substantial and compelling reasons justifying an
    26   exceptional sentence,” based on a non-exhaustive list of
    26
    1   aggravating factors.   
    Id.
     (quoting 
    Wash. Rev. Code § 2
       9.94A.120(2)).   The sentencing judge found that, in kidnapping
    3   his ex-wife, Blakely had acted with deliberate cruelty and
    4   accordingly sentenced him above the standard range to a term of
    5   incarceration of 90 months.   
    Id. at 300
    .
    6        The Supreme Court stated that review of Blakely’s sentence
    7   required “apply[ing] the rule we expressed in Apprendi v. New
    8   Jersey: ‘Other than the fact of a prior conviction, any fact that
    9   increases the penalty for a crime beyond the prescribed statutory
    10   maximum must be submitted to a jury, and proved beyond a
    11   reasonable doubt.’”    Blakely, 
    542 U.S. at 301
     (quoting Apprendi,
    12   
    530 U.S. at 490
    ) (citation omitted).   The Court then reiterated
    13   that “the ‘statutory maximum’ for Apprendi purposes is the
    14   maximum sentence a judge may impose solely on the basis of the
    15   facts reflected in the jury verdict or admitted by the
    16   defendant.”   Id. at 303 (emphasis in original).   Thus, for
    17   purposes of Apprendi, the statutory maximum for Blakely was not
    18   the 10 years prescribed for the class of felony, but the top of
    19   the standard range, 53 months, the applicable maximum absent
    20   additional fact-finding.   See id. at 303-04.   Because a judge had
    21   to find facts in order to impose a sentence beyond the 53 month-
    22   range, the Court concluded that Washington’s sentence violated
    23   the Sixth Amendment.   See id. at 313-14.
    24        In so holding, Blakely rejected the argument that the
    25   Apprendi rule did not apply because Washington’s sentencing laws
    26   did not require the finding of any specific fact or facts, but
    27
    1   rather required application of the amorphous test of “substantial
    2   and compelling reasons,” id. at 299, as a prerequisite for the
    3   imposition of a sentence enhanced beyond the standard range.    See
    4   id. at 305.    The Court explained that it was irrelevant
    5   “[w]hether the judge’s authority to impose an enhanced sentence
    6   depends on finding a specified fact (as in Apprendi), one of
    7   several specified facts (as in Ring), or any aggravating fact (as
    8   [in Blakely])) . . . .”    Id.   It also rejected as irrelevant the
    9   fact that a sentencing court, after finding aggravating facts,
    10   was required to assess the appropriateness of an enhanced
    11   sentence.    See id. at 305 n.8 (“Whether the judicially determined
    12   facts require a sentence enhancement or merely allow it, the
    13   verdict alone does not authorize the sentence.” (emphasis
    14   omitted)).    Because the judge-made “deliberate cruelty” finding
    15   resulted in Blakely being sentenced beyond 53 months, the Court
    16   reversed the state court’s decision that there was no Apprendi
    17   violation and remanded for further proceedings.    Id. at 298, 303,
    18   314.
    19           Blakely clarified Apprendi by making it unambiguously clear
    20   that any fact (other than a prior conviction), no matter how
    21   generalized or amorphous, that increases a sentence for a
    22   specific crime beyond the statutory maximum must be found by a
    23   jury.    Before Blakely, a court could reasonably have concluded
    24   (as was argued in Blakely) that certain kinds of judicial fact-
    25   finding did not violate Apprendi even if it resulted in a
    26   sentence beyond a statutory maximum.    Indeed, we so held in Brown
    28
    1   II, 
    451 F.3d at 55
    , and Brown I, 
    409 F.3d at 526
    .    Of course,
    2   those decisions involved the reasonableness of New York court
    3   decisions upholding the PFO statute before Blakely and do not
    4   answer the question before us with regard to four of the
    5   petitioners, as discussed infra.     See Brown II, 
    451 F.3d at
    59
    6   n.3; Brown I, 
    409 F.3d at
    533 & n.3.
    7        In Brown I, we concluded that it was not unreasonable to
    8   read Apprendi to proscribe only those sentencing schemes that
    9   permit a court to find some statutorily-enumerated, specific
    10   fact(s) to impose an enhanced sentence.    Brown I, 
    409 F.3d at
    11   534-35.   Brown II reconsidered that holding in light of Ring and
    12   concluded that Ring had not undermined Brown I.     Brown II, 451
    13   F.3d at 55.   We held that, even after Ring, it was not
    14   unreasonable “to conclude that [] determinations regarding the
    15   defendant’s history, character, and offense fall into a different
    16   category from the essential statutory elements of heightened
    17   sentencing, or functional equivalents thereof, that were
    18   addressed by the Supreme Court’s Apprendi ruling.”    Id. at 58
    19   (quoting Brown I, 
    409 F.3d at 535
    ).    In other words, because the
    20   “‘amorphous’ determination” required by the statute did not
    21   require “judicial factfinding of an element of the crime,” it did
    22   not violate Apprendi.   Id. at 59.    However, while Brown I and
    23   Brown II remain good law as to the issue they addressed --
    24   whether upholding the PFO statute was an unreasonable application
    25   of clearly established federal law after Apprendi but before
    26   Blakely/Cunningham -- Blakely makes it clear that even
    29
    1   “amorphous” judicial findings that alter maximum sentences offend
    2   the Sixth Amendment.
    3        Cunningham v. California, 
    127 S. Ct. 856
     (2007), also
    4   requires discussion because the challenged sentencing regime,
    5   California’s determinate sentencing law (“DSL”), bears a
    6   remarkable similarity to both the sentencing scheme in Blakely
    7   and the New York PFO statute.   Under the DSL, substantive
    8   offenses were assigned upper, middle, and lower range maximum
    9   sentences.   
    Id. at 861
    .   In Cunningham’s case, the lower range
    10   was 6 years, the middle range was 12 years, and the upper range
    11   was 16 years.   
    Id. at 860
    .   Sentencing judges were required to
    12   impose the middle range unless there were “circumstances in
    13   aggravation or mitigation of the crime.”   
    Id. at 861
     (quoting
    14   
    Cal. Penal Code § 1170
    (b)).   “Circumstances in aggravation,” were
    15   defined as “facts which justify the imposition of the upper
    16   prison term.”   
    Id. at 862
     (quoting Cal. Jud. Council Rule
    17   4.405(d)) (emphasis omitted).   Such facts were to be “established
    18   by a preponderance of the evidence,” and “stated orally on the
    19   record.”   
    Id.
     (quoting Cal. Jud. Council Rule 4.420(b), (e)).
    20        The Supreme Court held in Cunningham that “[b]ecause
    21   circumstances in aggravation are found by the judge, not the
    22   jury, and need only be established by a preponderance of the
    23   evidence, not beyond a reasonable doubt, the DSL violates
    24   Apprendi’s bright-line rule.”   
    Id. at 868
     (citations omitted).
    25   In reaching this conclusion, the Court rejected the contention
    26   that the upper range was the relevant statutory maximum for
    30
    1   Apprendi purposes and that judges were simply exercising the
    2   traditional discretion common to sentencing.   
    Id.
       It reiterated
    3   that “[i]f the jury’s verdict alone does not authorize the
    4   sentence, if, instead, the judge must find an additional fact to
    5   impose the longer term, the Sixth Amendment requirement is not
    6   satisfied.”   
    Id. at 869
    .
    7        Cunningham also rejected an attempt to compare California’s
    8   mandatory sentencing scheme and the post-Booker Federal
    9   Sentencing Guidelines, 
    id. at 869-70
    , which had been rendered
    10   advisory by the Court, see United States v. Booker, 
    543 U.S. 220
    ,
    11   246 (2005) (Breyer, J., for the Court).   That the sentencing
    12   schemes of both California and the United States required that
    13   resultant sentences be reasonable did not, in the Court’s view,
    14   cure the California scheme’s constitutional infirmity in
    15   requiring judges to find facts to impose the increase in a
    16   sentence beyond the maximum sentence prescribed by the middle
    17   range.   See Cunningham, 
    127 S. Ct. at 870
    .
    18        2) Was Blakely “clearly established” at the relevant time
    19   for each petitioner?
    20        As noted, the legal rule invoked by petitioners was not
    21   clearly established until Blakely clarified Apprendi.     Therefore,
    22   we must decide whether Blakely was clearly established federal
    23   law “as of the time of the relevant state-court decision” for
    24   each petitioner.   Williams, 
    529 U.S. at 412
     (O’Connor, J., for
    25   the Court).   If Blakely postdates the “relevant time” for any
    26   petitioner, then our Brown cases would control and foreclose the
    31
    1   current challenge.   See Brown II, 
    409 F.3d at 535
    ; Brown I, 451
    2   F.3d at 59.
    3        For all but one petitioner, it does not matter which formula
    4   we use in assessing the “relevant time.”     Besser’s conviction
    5   became final well before Blakely, and our Brown decisions dispose
    6   of his claim for habeas relief.    Similarly, because the state
    7   court decisions involving Portalatin, Morris and Washington all
    8   postdate Blakely, their claims are not controlled by the Brown
    9   decisions, and we must instead evaluate New York’s sentencing law
    10   in light of Blakely.   However, Blakely came down after the New
    11   York Appellate Division decided Phillips’ appeal but before the
    12   Court of Appeals of New York denied Phillips leave to appeal.
    13   Phillips’ appeal thus turns on which approach we adopt in
    14   determining the relevant time.
    15        We have previously noted that the Supreme Court has offered
    16   “inconsistent guidance” on this question.     See Brown II, 
    451 F.3d 17
       at 57 n.1; Brown I, 
    409 F.3d at
    533 n.3.10    However, as the Court
    18   recently explained, “the relevant state-court judgment for
    19   purposes of our review under AEDPA is that adjudicating the
    20   merits of [petitioner’s] state habeas application, in which these
    21   claims were properly raised . . . .”   Abdul-Kabir v. Quarterman,
    22   
    127 S. Ct. 1654
    , 1659 (2007).
    23        We understand this formulation to mean that any state court
    24   decision involving the merits of an Apprendi claim is an
    25   application of federal law, whether or not the decision contains
    26   a discussion.   Even if such a decision is a denial of leave to
    32
    1   appeal or denial of a motion for reconsideration, application of
    2   federal law is still a factor that we must deem a state court to
    3   have considered.   Therefore, we understand the relevant time to
    4   be the date on which a decision regarded as final under state law
    5   -- which may or may not include the certiorari period (not an
    6   issue here) -- has been entered in a proceeding deemed to involve
    7   the merits for federal habeas purposes.   We believe that rule is
    8   not only fully consistent with Section 2254(d), which triggers
    9   AEDPA review once a claim has been “adjudicated on the merits in
    10   State court proceedings,” 
    28 U.S.C. § 2254
    (d), but also provides
    11   a bright-line rule.
    12        Applying this formulation here, Phillips may rely on Blakely
    13   as clearly established while the state courts were actively
    14   reviewing his claims.   Thus, Blakely is clearly established law
    15   for purposes of the petitions filed by Portalatin, Morris,
    16   Washington, and Phillips.
    17        3) Cunningham and “Clearly Established” Law
    18        We turn to a final issue related to the term “clearly
    19   established federal law.”   As noted, Cunningham invalidated a
    20   statutory scheme very similar to the PFO statute.   The state
    21   argues that we may not consider Cunningham because it postdates
    22   the relevant state court decisions for the remaining petitioners.
    23   We disagree.   Under both AEDPA and Teague, a petitioner may rely
    24   on a decision issued subsequent to the relevant period if that
    25   decision is “dictated” by preexisting Supreme Court precedent.
    26   See Artuz, 
    326 F.3d at 96
    ; see also Williams, 
    529 U.S. at
    381
    33
    1   (Stevens, J., concurring) (quoting Teague, 
    489 U.S. at 301
    ); 
    id.
    2   at 412 (O’Connor, J., for the Court).     By “dictated,” we mean
    3   that the result must have been “apparent to all reasonable
    4   jurists” during the operative time frame.    See Beard v. Banks,
    5   
    542 U.S. 406
    , 413 (2004) (quoting Lambrix v. Singletary, 
    520 U.S. 6
       518, 528 (1997)).    Accordingly, neither Teague nor AEDPA preclude
    7   us from considering post-dated decisions that merely restate or
    8   codify “old” rules of law that were “clearly established” at the
    9   time.
    10           Applying that principle here, we conclude that Blakely
    11   compelled the result in Cunningham and that we must therefore
    12   consider it as “clearly established law” for AEDPA purposes.
    13   Cunningham presented no issue of fact or law materially
    14   distinguishable from Blakely because the sentencing schemes in
    15   Blakely and Cunningham were “closely analogous.”     See Butler v.
    16   Curry, 
    528 F.3d 624
    , 635-36 (9th Cir. 2008).     Both schemes
    17   required a judge to impose a sentence within a standard range
    18   absent a finding of circumstances (other than those taken into
    19   account in the conviction) justifying an enhanced sentence.       See
    20   Cunningham, 
    127 S. Ct. at 861-62
    ; Blakely, 
    542 U.S. at 304
    .        And
    21   we agree with the Ninth Circuit that Cunningham, in rejecting
    22   California’s scheme, merely “reiterated the[] same points,
    23   rejecting arguments already disapproved in Blakely. . . .        [It]
    24   did not add ‘“any new elements or criteria for”’ determining when
    25   a state statute violates the Sixth Amendment.”    Butler, 
    528 F.3d 26
       at 636 (citation omitted).
    34
    1        To be sure, the statutory scheme in Blakely is not precisely
    2   identical to the scheme in Cunningham.     But a decision does not
    3   announce a “new” legal rule simply because it applies “a
    4   well-established constitutional principle to govern a case which
    5   is closely analogous to those which have been previously
    6   considered in the prior case law.”     Penry v. Lynaugh, 
    492 U.S. 7
       302, 314 (1989) (quoting Mackey v. United States, 
    401 U.S. 667
    ,
    8   695 (1971) (Harlan, J., concurring in part and dissenting in
    9   part)), abrogated on other grounds by Atkins v. Virginia, 536
    
    10 U.S. 304
    , 307, 321 (2002).    Holding otherwise would render any
    11   application of Blakely a “new” rule and thus not “clearly
    12   established law” for AEDPA purposes.    See Butler, 
    528 F.3d at
    13   638-39; see also Duncan v. United States, 
    552 F.3d 442
    , 445 (6th
    14   Cir. 2009) (“[T]he Apprendi line of cases is long.    Logically, at
    15   some point in this chain . . . the rule Apprendi announced must
    16   stop being a new rule in every varying application and instead
    17   must become an old one that applies on collateral review.”).
    18        Because Cunningham presented no issue of law or fact
    19   materially distinguishable from Blakely, we conclude that Blakely
    20   dictated the result in Cunningham.     Indeed, the Court’s opinion
    21   in Cunningham suggests as much.    See Cunningham, 
    127 S. Ct. at
    22   868 (“[T]hat should be the end of the matter . . . .” (quoting
    23   Blakely, 
    542 U.S. at 313
    )).    As such, we may consider it in
    24   determining whether the state courts here unreasonably applied
    25   clearly established federal law.
    35
    1   c) AEDPA and “Contrary to,” or “Unreasonable Application” of
    2   “Clearly Established Law”
    3          In rejecting the Sixth Amendment challenges of Phillips,
    4   Portalatin, Morris and Washington to the PFO statute, New York
    5   courts relied on the views expressed by the Court of Appeals in a
    6   series of opinions.   We now turn to whether, in view of Blakely
    7   and Cunningham, those decisions are “contrary to” or an
    8   “unreasonable application of” clearly established Sixth Amendment
    9   law.
    10          The New York Court of Appeals has considered Apprendi
    11   arguments with regard to the PFO statute on at least three
    12   occasions and each time has concluded that the scheme is
    13   constitutional.   See Quinones, 
    906 N.E.2d 1033
    ; Rivera, 833
    
    14 N.E.2d 194
    ; Rosen, 
    752 N.E.2d 844
    .    Rivera, decided after Blakely
    15   and Booker, elaborates on Rosen and offers the most thorough
    16   interpretation and analysis of the PFO statute.   The court’s more
    17   recent decision in Quinones merely reiterates and confirms the
    18   logic of Rosen and Rivera.    Compare Quinones, 906 N.E.2d at 1036-
    19   42, with Rivera, 833 N.E.2d at 197-201, and Rosen, 752 N.E.2d at
    20   846-47.
    21          In upholding the PFO statute, Rivera emphasized that the
    22   history/character/criminal conduct findings are of the sort that
    23   have always guided the exercise of discretion in sentencing,
    24   Rivera, 833 N.E.2d at 199-200, and that “fall[] squarely within
    25   the most traditional discretionary sentencing role of the judge.”
    26   Id. at 200.   By way of footnote, Rivera noted:
    36
    1                   . . . Our statutes contemplate that
    2              the sentencing court–after it has
    3              adjudicated the defendant a persistent
    4              felony offender–will consider
    5              holistically the defendant’s entire
    6              circumstances and character, including
    7              traits touching upon the need for
    8              deterrence, retribution and
    9              rehabilitation unrelated to the crime of
    10              conviction. This is different from the
    11              type of factfinding involved in
    12              Apprendi. In this respect, we note that
    13              in Brown v. Greiner, 
    409 F.3d 523
    , 534
    14              [(2d Cir. 2005)], the United States
    15              Court of Appeals for the Second Circuit
    16              described the contested second phase of
    17              our sentencing procedure as “a vague,
    18              amorphous assessment” of whether the
    19              public interest would be served through
    20              imposition of the recidivist sentence.
    21
    22   
    Id.
     at 200 n.8.   The Court of Appeals also analogized the
    23   history/character/criminal conduct findings to the federal
    24   Guidelines provision in Section 3553(a).   See id. at 199.
    25   Finally, it concluded, “[o]nce the defendant is adjudicated a
    26   persistent felony offender, the requirement that the sentencing
    27   justice reach an opinion as to the defendant’s history and
    28   character is merely another way of saying that the court should
    29   exercise its discretion.”   Id. at 201.
    30        To reiterate our earlier discussion of New York’s sentencing
    31   scheme:   first felony offenders are generally subject to a low
    32   minimum and a maximum that varies greatly depending on the crime,
    33   see 
    N.Y. Penal Law § 70.00
    ; second felony offenders are generally
    34   subject to a higher minimum and a maximum that is the same as
    35   that for first felony offenders, see 
    N.Y. Penal Law § 70.06
    ; a
    36   defendant with two felony convictions is a PFO subject to a Class
    37   A-I maximum of life but may be sentenced within a lower range,
    37
    1   usually as a second felony offender or second violent felony
    2   offender, if the prosecution fails to show that the
    3   history/character/criminal conduct factors justify a Class A-I
    4   sentence, see 
    N.Y. Penal Law § 70.10
    ; 
    N.Y. Crim. Proc. Law § 5
       470.20.   We believe that upholding this scheme was an
    6   unreasonable application of Blakely/Cunningham.     There is no
    7   material difference between the PFO statute and the schemes that
    8   the Supreme Court found objectionable in Blakely/Cunningham.
    9        Under both the Washington law at issue in Blakely and the
    10   California law challenged in Cunningham, the convicted defendant
    11   was “eligible for” or “subject to” a sentencing range with a high
    12   maximum.11   See Cunningham, 
    127 S. Ct. at 861-62
    ; Blakely, 542
    13   U.S. at 299.   However, before a sentencing court could exercise
    14   its discretion to impose a sentence in the range with the high
    15   maximum, it had to conclude that some aggravating or compelling
    16   circumstance justified it.   See Cunningham, 
    127 S. Ct. at
    861
    17   (allowing for an enhanced sentence upon the finding of
    18   “circumstances in aggravation”); Blakely, 
    542 U.S. at
    299
    19   (allowing for enhanced sentencing upon a finding of “substantial
    20   and compelling reasons”).    In the absence of such findings, these
    21   sentencing courts lacked any discretion to sentence above the
    22   standard range that had a lower maximum.    See Cunningham, 127 S.
    23   Ct. at 862; Blakely, 
    542 U.S. at 304
    .     Additionally, under both
    24   schemes, a decision to sentence above the standard range was
    25   reviewable for evidentiary sufficiency.    See Cunningham, 127 S.
    26   Ct. at 861 n.2; Blakely, 
    542 U.S. at 299-300, 304
    .
    38
    1        New York’s scheme is virtually indistinguishable in these
    2   respects.   The law allows higher-tier, Class A-I sentencing when
    3   the sentencing judge has made factual findings related to a
    4   defendant’s criminal history, character, and nature of the
    5   criminal conduct that justify the higher sentencing range.    See
    6   
    N.Y. Penal Law § 70.10
    (2); 
    N.Y. Crim. Proc. Law § 400.20
    (1);
    7   Rivera, 833 N.E.2d at 197 n.3 (“The law goes on to require a
    8   hearing or hearings, at which the People must prove to the court,
    9   beyond a reasonable doubt, the fact of defendant’s prior
    10   convictions, and either party may offer evidence (subject to a
    11   preponderance-of-the-evidence standard) bearing on the court’s
    12   exercise of discretion as to whether a recidivist sentence is
    13   warranted.” (citation omitted)).     To be sure, the quantity and
    14   quality of the prior offenses alone may suffice to show facts
    15   justifying a Class A-I sentence.     See Rivera, 833 N.E.2d at 201
    16   (“If, for example, a defendant had an especially long and
    17   disturbing history of criminal convictions, a persistent felony
    18   offender sentence might well be within the trial justice’s
    19   discretion even with no further factual findings.”).    Absent such
    20   fact-finding, a judge lacks discretion to select the Class A-I
    21   sentence and must provide a sentence authorized by the other
    22   provisions of Article 70, such as a second felony offender
    23   sentence.   See 
    N.Y. Penal Law § 70.10
    (2); 
    N.Y. Crim. Proc. Law § 24
       400.20(1); Rivera, 833 N.E.2d at 198 (“Criminal Procedure Law §
    25   400.20(1) provides that a defendant may not be sentenced as a
    26   persistent felony offender until the court has made the requisite
    39
    1   judgment as to the defendant’s character and the criminality.”).
    2   Moreover, as in Blakely, an enhanced sentence under New York law
    3   is subject to a standard of appellate review focused on the
    4   judge’s role as fact-finder in imposing the enhanced sentence.
    5   See Blakely, 
    542 U.S. at 299-300
    ; Rivera, 833 N.E.2d at 199
    6   (“[O]nce a defendant is adjudged a persistent felony offender, a
    7   recidivism sentence cannot be held erroneous as a matter of law,
    8   unless the sentencing court acts arbitrarily or irrationally.”);
    9   People v. Jennings, 
    822 N.Y.S.2d 501
    , 502 (App. Div. 2006) (“The
    10   adjudication of defendant as a persistent felony offender was not
    11   an abuse of discretion.”).   We thus see no material difference
    12   between the elements of the PFO statute and the elements of the
    13   sentencing schemes found objectionable in Blakely and Cunningham.
    14        For the reader’s benefit, we include a chart comparing the
    15   sentences that Blakely and Cunningham were subject to, see
    16   generally Cunningham, 237 S. Ct. at 861; Blakely, 
    542 U.S. at
    17   299, with the sentences petitioner Morris was subject to under
    18   the New York scheme.
    40
    1                      “Lesser”       Requisite Judicial    “Enhanced” or
    Sentence         Fact-Finding to      “Upper Tier”
    Enhance Sentence        Sentence
    2    Washington     “Standard” term    “substantial and    10-year Maximum
    3    Sentencing            of         compelling reasons       Sentence
    4        Law        49 to 53 months      justifying an
    5                                         exceptional
    6    (Blakely)                             sentence”
    7
    8
    9   second-degree   Wash. Rev. Code    Wash. Rev. Code     Wash. Rev. Code
    10     kidnapping     §§ 9.94A.310,      § 9.94A.120(2)             §
    11        with a        9.94A.320                            9A.20.021(1)(b)
    12       firearm
    13    California      “Middle” term      “the court shall   16-year Maximum
    14        DSL               of           order imposition       Sentence
    15                       12 years          of the middle
    16   (Cunningham)                      term, unless there
    17                                      are circumstances
    18                                      in aggravation or
    19                                      mitigation of the
    20                                             crime”
    21
    22    continuous     Cal. Penal Code   Cal. Penal Code §    Cal. Penal Code
    23   sexual abuse       § 288.5(a)          1170(b)            § 288.5(a)
    24    of a child
    25     under 14
    26    New York’s      Second Felony      Two qualifying       Indeterminate
    27    Sentencing         Offender         prior felony      term of 15 years
    28      Scheme         Sentence –         convictions            to life
    29
    30     (Morris)      indeterminate            AND
    31                   term of 1.5 to
    32                       4 years        “the court . . .
    33                                     is of the opinion
    34                                      that the history
    35      Class E      N.Y. Penal Law     and character of     N.Y. Penal Law
    36       felony      § 70.06(3)-(4)    the defendant and    §§ 70.00(2)-(3),
    37    conviction                         the nature and          70.10(2)
    38                                      circumstances of
    his criminal
    conduct indicate
    that extended
    incarceration and
    life-time
    supervision will
    best serve the
    public interest”
    
    N.Y. Penal Law § 70.10
    39
    41
    1          In addition, the statutory labels “history and character”
    2   and “nature and circumstances of [the] criminal conduct” can no
    3   longer (after Blakely/Cunningham) reasonably be described as the
    4   kind of judicial fact-finding constitutionally permissible, see
    5   Almendarez-Torres v. United States, 
    523 U.S. 224
    , 226-27 (1998),
    6   because they are amorphous and do not involve hard facts.      The
    7   Blakely standard determined to be a jury question was only
    8   “substantial and compelling reasons,” see Blakely, 
    542 U.S. at
    9   299, while the corresponding test in Cunningham was
    10   “circumstances in aggravation,” see Cunningham, 
    127 S. Ct. at
    11   861.   If anything, the PFO statute’s history/character/criminal
    12   conduct standard is less amorphous than those.    Finally,
    13   Cunningham rejected the attempted analogy to the federal
    14   guidelines.   See 
    id. at 869-71
    .
    15          To sum up, the PFO statute cannot be squared with the
    16   statement by Justice Ginsburg in her opinion for the Court in
    17   Cunningham:    “If the jury’s verdict alone does not authorize the
    18   sentence, if, instead, the judge must find an additional fact to
    19   impose the longer term, the Sixth Amendment requirement is not
    20   satisfied.”   
    Id. at 869
    .
    21   d) Harmless Error
    22          However, it is not enough to conclude that New York state
    23   courts have unreasonably applied the Sixth Amendment to Phillips,
    24   Washington, Morris, and Portalatin.     The state also contends that
    25   any constitutional error in their sentencing was harmless.     In
    26   light of our conclusion that the state court decisions affirming
    42
    1   Besser’s sentence were not unreasonable applications of clearly
    2   established law, we need not discuss this issue with respect to
    3   him.
    4          Many constitutional errors are not such as to “necessarily
    5   render[] a criminal trial fundamentally unfair or an unreliable
    6   vehicle for determining guilt or innocence.”   Washington v.
    7   Recuenco, 
    548 U.S. 212
    , 218-19 (2006) (quoting Neder v. United
    8   States, 
    527 U.S. 1
    , 9 (1999)).    So long as the “defendant had
    9   counsel and was tried by an impartial adjudicator, there is a
    10   strong presumption that any other [constitutional] errors that
    11   may have occurred are subject to harmless-error analysis.”     
    Id.
    12   at 218 (quoting Neder, 
    527 U.S. at 8
    ) (alteration in original).
    13   Accordingly, the Supreme Court has held that a state court’s
    14   failure to submit a sentencing factor to the jury, a Sixth
    15   Amendment violation under Blakely, is not structural error and is
    16   subject to harmless error analysis.   Id. at 221-22.
    17          In deciding whether the application of the unconstitutional
    18   statute to each petitioner was harmless, we must apply the Brecht
    19   v. Abrahamson, 
    507 U.S. 619
     (1993), test and ask if the error
    20   “had substantial and injurious effect or influence” on the
    21   sentence.    
    Id. at 631
     (quoting Kotteakos v. United States, 328
    
    22 U.S. 750
    , 776 (1946)); see also Fry v. Pliler, 
    127 S. Ct. 2321
    ,
    23   2328 (2007) (holding that a federal habeas “court must assess the
    24   prejudicial impact of constitutional error in a state-court
    25   criminal trial under the substantial and injurious effect
    26   standard . . . , whether or not the state appellate court
    43
    1   recognized the error . . .”) (internal quotation marks omitted);
    2   Recuenco, 
    548 U.S. at 221-22
    ; Calderon v. Coleman, 
    525 U.S. 141
    ,
    3   145-47 (1998) (per curiam) (holding that for habeas relief to be
    4   granted based on constitutional error in the capital penalty
    5   phase, the error must have had substantial and injurious effect
    6   on the jury’s verdict in the penalty phase); Brinson v. Walker,
    7   
    547 F.3d 387
    , 395 (2d Cir. 2008); Butler, 
    528 F.3d at 648
    .
    8          The State bears the burden of persuasion in such cases, Fry,
    9   127 S. Ct. at 2327 n.3; United States v. Dominguez Benitez, 542
    
    10 U.S. 74
    , 81 n.7 (2004), and “in cases of grave doubt as to
    11   harmlessness the petitioner must win,” O’Neal v. McAninch, 513
    
    12 U.S. 432
    , 437 (1995).   Grave doubt exists when, “in the judge’s
    13   mind, the matter is so evenly balanced that he feels himself in
    14   virtual equipoise as to the harmlessness of the error.”     
    Id.
     at
    15   435.
    16          In the present case, we believe it prudent to remand for
    17   further proceedings on the question of harmlessness.   No district
    18   court made a detailed analysis of the harmless error issue with
    19   respect to the sentences for the four petitioners, and we do not
    20   believe the record on appeal is sufficiently developed for us to
    21   address the matter accurately in the first instance.   We
    22   therefore remand the remaining four petitions for proceedings
    23   consistent with this opinion.
    24                                CONCLUSION
    25          We have considered the parties’ remaining claims and find
    26   them to be without merit.   For the foregoing reasons, we affirm
    44
    1   the district court’s order in Besser.   We vacate and remand in
    2   Portalatin, Washington, Morris, and Phillips.   Any subsequent
    3   appeal in any of the remanded cases should be referred for
    4   decision to this panel in light of the time it has invested in
    5   these matters.   All parties to such an appeal are directed to
    6   inform the clerk of our instruction.
    7
    45
    1                                  FOOTNOTES
    2
    3   1.   We use the term “state authorities” to refer collectively to
    the various state officials that have filed briefs as appellants
    or appellees.
    2.   Because a defendant sentenced to an indeterminate sentence
    receives a sentence that is a range of years, rather than a set
    term, the New York statutes frequently refer to the “maximum
    term” and the “minimum period of imprisonment.”     See, e.g., 
    N.Y. Penal Law § 70.00
    (2)-(3).     This should not be confused with this
    opinion’s use of the terms “maximum” and “minimum,” which are
    used to refer to the outer boundaries of the sentence, rather
    than a specific range, that a defendant could permissibly
    receive.
    3.   The PFO statute reads:
    1. Definition of persistent felony
    offender.
    (a) A persistent felony offender is
    a person, other than a persistent
    violent felony offender as defined in
    section 70.08, who stands convicted of a
    felony after having previously been
    convicted of two or more felonies, as
    provided in paragraphs (b) and (c) of
    this subdivision.
    (b) A previous felony conviction
    within the meaning of paragraph (a) of
    this subdivision is a conviction of a
    felony in this state, or of a crime in
    any other jurisdiction, provided:
    46
    (i) that a sentence to a term of
    imprisonment in excess of one year, or a
    sentence to death, was imposed therefor;
    and
    (ii) that the defendant was
    imprisoned under sentence for such
    conviction prior to the commission of
    the present felony; and
    (iii) that the defendant was not
    pardoned on the ground of innocence; and
    (iv) that such conviction was for a
    felony offense other than persistent
    sexual abuse, as defined in section
    130.53 of this chapter.
    (c) For the purpose of determining
    whether a person has two or more
    previous felony convictions, two or more
    convictions of crimes that were
    committed prior to the time the
    defendant was imprisoned under sentence
    for any of such convictions shall be
    deemed to be only one conviction.
    2. Authorized sentence. When the
    court has found, pursuant to the
    provisions of the criminal procedure
    law, that a person is a persistent
    felony offender, and when it is of the
    opinion that the history and character
    of the defendant and the nature and
    circumstances of his criminal conduct
    indicate that extended incarceration and
    life-time supervision will best serve
    the public interest, the court, in lieu
    of imposing the sentence of imprisonment
    authorized by section 70.00, 70.02,
    70.04, 70.06 or subdivision five of
    section 70.80 for the crime of which
    such person presently stands convicted,
    may impose the sentence of imprisonment
    authorized by that section for a class
    A-I felony. In such event the reasons
    for the court’s opinion shall be set
    forth in the record.
    
    N.Y. Penal Law § 70.10
    .
    47
    4.   Because the maximum sentence for a Class A felon is already
    life imprisonment, see 
    N.Y. Penal Law § 70.00
    (2)(a), neither the
    second felony offender nor the PFO statute alters the maximum
    sentence for such convicted defendants.    Defendants convicted of
    lesser felony classes (except for a terrorist offense, see 
    N.Y. Penal Law § 490.25
    (2)(c), of no pertinence here) may be subject
    to a maximum sentence of life imprisonment only by virtue of the
    PFO statute, see 
    id.
     §§ 70.00-70.06, 70.10(2), or the persistent
    violent felony offender statute, see id. § 70.08(2); see also
    infra note 5.
    5.   There are also three increasingly harsh tiers that apply to
    the sentencing for those convicted of a “violent felony offense.”
    A violent felony offense is specified by statute and includes a
    broad range of criminal activity.    See 
    N.Y. Penal Law § 70.02
    (1).
    A first-time felony offender convicted of a violent felony
    offense is generally sentenced to a determinate sentence based on
    the class of offense.   See 
    id.
     § 70.02.   Moreover, if there is a
    finding that the violent felony offender was previously convicted
    of one qualifying prior violent felony conviction, the defendant
    is sentenced to a determinate sentence as a second violent felony
    offender.   See id. § 70.04.
    If there is a finding that the violent felony offender was
    previously convicted of one qualifying felony conviction, as
    opposed to one qualifying violent felony conviction, the
    defendant is sentenced to a determinate sentence as a second
    48
    felony offender.    See id. § 70.06(6).    While the minimum
    determinate sentence a second violent felony offender may receive
    is greater than the minimum determinate sentence a second felony
    offender convicted of a violent felony may receive, the maximum
    determinate sentence that may be imposed is the same.     Compare
    id. § 70.04 with id. § 70.06(6).
    Article 70 also includes a persistent violent felony
    offender provision.     See id. § 70.08.   A persistent violent
    felony offender, as opposed to a persistent felony offender, is
    “a person who stands convicted of a violent felony offense . . .
    or the offense of predatory sexual assault . . . or the offense
    of predatory sexual assault against a child . . . , after having
    previously been subjected to two or more predicate violent felony
    convictions . . . .”     Id. § 70.08(1)(a).   This persistent
    offender provision requires imposition of an indeterminate
    sentence with a statutory maximum of life imprisonment solely
    upon the court’s finding of qualifying predicate convictions.
    Id. § 70.08(2).    However, this provision is not at issue in this
    appeal.
    6.   The pertinent provision reads:
    [A Class A-I] sentence may not be
    imposed unless, based upon evidence
    in the record of a hearing held
    pursuant to this section, the court
    (a) has found that the defendant is
    a persistent felony offender as
    defined in subdivision one of
    section 70.10 of the penal law, and
    (b) is of the opinion that the
    history and character of the
    49
    defendant and the nature and
    circumstances of his criminal
    conduct are such that extended
    incarceration and lifetime
    supervision of the defendant are
    warranted to best serve the public
    interest.
    
    N.Y. Crim. Proc. Law § 400.20
    (1).
    7.   With regard to a PFO convicted of a Class C, D, or E felony,
    there is a sentencing “dead-zone” between the legally-authorized
    sentencing ranges available to a court.   For example, in the case
    of a PFO convicted of a Class D felony, a court may impose a
    sentence within a range of 15 years to life imprisonment if it
    has found facts relevant to history/character/criminal conduct
    that warrant such a sentence.   See 
    N.Y. Penal Law §§ 70.00
    (2)-
    (3), 70.10(2).   If the court’s fact-finding causes it to exercise
    its discretion not to impose a PFO sentence, then the statutory
    maximum (if not a persistent violent felony offender) generally
    available to the court is 7 years.    See 
    id.
     §§ 70.00(2)(d),
    70.02(3)(c), 70.04(3)(c), 70.06(3)(d).    In such a case, a court
    may not impose a sentence within a range of 8 to 14 years, as no
    provision of New York law makes that a legally-authorized
    sentencing range.   See People v. Jennings, 
    822 N.Y.S.2d 501
    , 502
    (App. Div. 2006) (“If the sentencing court had not found
    defendant a persistent felony offender, the maximum sentence it
    could have imposed would have been an indeterminate term of 2 to
    4 years, the same sentence defendant received for each of his
    prior two felonies.”); see also People v. Wilsey, 
    753 N.Y.S.2d 50
    232, 233 (App. Div. 2003); People v. Yale, 
    373 N.Y.S.2d 901
    , 904-
    06 (App. Div. 1975).   With regard to Class B felons, a different
    kind of dead-zone exists.   These felons may be sentenced within
    the Class A-I range, but with maximum sentences of 25, see 
    N.Y. Penal Law §§ 70.00
    (2)(b), 70.02(3)(a), 70.04(3)(a), 70.06(3)(b),
    70.06(6)(a), or 30 years, see 
    id.
     § 70.02(3)(a).     The dead zone
    here is between the maximum term of years and life imprisonment.
    Such PFOs may be sentenced to life imprisonment if the requisite
    fact-findings as to history/character/criminal conduct are made.
    See id. § 70.10(2); 
    N.Y. Crim. Proc. Law § 400.20
    (1).
    8.    New York’s Penal Law has since been amended, and now
    violations of New York Penal Law § 160.10(1) are Class C felony
    offenses.
    9.    We certified three issues:   (i) which date -– that of the
    entry of the Appellate Division’s opinion, the date the New York
    Court of Appeals denied leave to appeal, or the date upon which
    the conviction became final -– is the relevant time for
    determining the applicable Supreme Court precedent; (ii) if
    Blakely v. Washington, 
    542 U.S. 296
     (2004), applies, whether the
    state court’s determination was an unreasonable application of
    the holding in that case; and (iii) what is the effect, if any,
    of People v. Rivera, 
    833 N.E.2d 194
     (N.Y. 2005).
    10.   The confusion originates with Williams v. Taylor, 
    529 U.S. 51
    362 (2000), which considered the interplay between AEDPA and
    Teague v. Lane, 
    489 U.S. 288
     (1988).     See Williams, 
    529 U.S. at 412
     (O’Connor, J., for the Court).     As we noted earlier, the
    Court read the term “clearly established federal law” as
    generally codifying Teague v. Lane’s rule against retroactive
    application of cases announcing “new” legal rules.     See 
    id. at 390-91
     (Stevens, J., for the Court) (citing Teague, 
    489 U.S. at 301
    ).   However, the court gave two different answers as to
    whether the operative period for assessing “clearly established”
    law was the same as the period for determining whether a rule is
    “new” for Teague purposes.     Under Teague, the relevant period is
    “the time the defendant’s conviction became final.”     See Teague,
    
    489 U.S. at 301
     (O’Connor, J., concurring).     Justice Stevens,
    speaking for the Court, concluded that the relevant period for
    AEDPA purposes was the same.    See Williams, 
    529 U.S. at 390
    (Stevens, J., for the Court).    Justice O’Connor, speaking later
    for the Court, concluded that habeas courts should look to
    “clearly established” law at the time of the “relevant state-
    court decision” or “state-court adjudication.”    
    Id. at 412
    (O’Connor, J., for the Court).
    11.   Indeed, the statute in Blakely stated that the maximum
    sentence for the crime was the higher limit but was held
    unconstitutional because a “standard” sentencing range with a
    lower limit was mandatory absent the required findings.    See
    Blakely, 
    542 U.S. at 299, 303-05
    .
    52