United States v. Guadalupe Velazquez , 855 F.3d 1021 ( 2017 )


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  •                        FOR PUBLICATION
    UNITED STATES COURT OF APPEALS
    FOR THE NINTH CIRCUIT
    UNITED STATES OF AMERICA,                              No. 14-10311
    Plaintiff-Appellee,
    D.C. No.
    v.                             2:12-cr-00877-
    JAT-4
    GUADALUPE VELAZQUEZ,
    Defendant-Appellant.
    OPINION
    Appeal from the United States District Court
    for the District of Arizona
    James A. Teilborg, Senior District Judge, Presiding
    Argued and Submitted November 18, 2016
    San Francisco, California
    Filed May 1, 2017
    Before: Alex Kozinski, Ronald Lee Gilman, * and
    Michelle T. Friedland, Circuit Judges.
    Opinion by Judge Friedland;
    Concurrence by Judge Kozinski
    *
    The Honorable Ronald Lee Gilman, United States Circuit Judge
    for the U.S. Court of Appeals for the Sixth Circuit, sitting by designation.
    2                UNITED STATES V. VELAZQUEZ
    SUMMARY **
    Criminal Law
    The panel vacated the defendant’s convictions that
    resulted from her guilty plea, and remanded for further
    proceedings, in a case in which the defendant argued that she
    was constructively denied her right to counsel.
    The panel held that the district court abused its discretion
    by denying the defendant’s requests to substitute counsel
    without conducting an adequate inquiry. The panel observed
    that (1) the defendant did everything in her power to alert the
    court to her belief that she was receiving inadequate
    assistance of counsel, and the district court never conducted
    any meaningful inquiry into her concerns about her counsel
    or their relationship; (2) the record reflects serious
    breakdowns in communication and trust; (3) the defendant’s
    two motions to substitute counsel, and three attempts to
    argue that her attorney had not advised her on the plea, were
    all made in advance of her plea deadline and more than a
    month before trial; and (4) even if her motions could be
    considered untimely, the court’s failure to conduct an
    adequate inquiry and the extent of the conflict outweigh any
    untimeliness.
    Rejecting the government’s argument that any concerns
    the defendant had about her counsel were remedied by
    meetings she had with him, the panel wrote that there is a
    substantial risk that the defendant agreed that she was
    **
    This summary constitutes no part of the opinion of the court. It
    has been prepared by court staff for the convenience of the reader.
    UNITED STATES V. VELAZQUEZ                 3
    satisfied with her attorney’s performance because the
    magistrate judge pressured her to accept the plea and she
    knew that she had to make that statement to enter the plea.
    Concurring, Judge Kozinski wrote only to note that the
    judges below acted with what they believed to be the
    defendant’s best interest at heart.
    COUNSEL
    Michael J. Bresnehan (argued), Law Offices of Michael J.
    Bresnehan P.C., Tempe, Arizona, for Defendant-Appellant.
    Keith E. Vercauteren (argued), Assistant United States
    Attorney; Krissa M. Lanham, Deputy Appellate Chief;
    United States Attorney’s Office, Phoenix, Arizona; for
    Plaintiff-Appellee.
    OPINION
    FRIEDLAND, Circuit Judge:
    Guadalupe Velazquez seeks to vacate a guilty plea on the
    ground that she was constructively denied her right to
    counsel when the district court denied her motions to
    substitute counsel without conducting an adequate inquiry.
    We agree that the district court abused its discretion in
    denying Velazquez’s motions and thus vacate the
    convictions that resulted from her plea.
    4             UNITED STATES V. VELAZQUEZ
    I. BACKGROUND
    Guadalupe Velazquez was in her late teens and on a
    scholarship at Arizona State University when she began
    dating Hector Ortiz, Jr. At some point, Ortiz and his father
    began running a drug-trafficking organization that shipped
    marijuana across the United States and laundered the
    proceeds. Local police and federal agents compiled
    evidence against the organization, including photographs
    and videos of Velazquez dropping off marijuana shipments
    at UPS. When police executed a search warrant on the home
    that Velazquez shared with Ortiz, they found guns,
    ammunition, and large quantities of marijuana.
    Ortiz, his father, Velazquez, and nine other associates
    were indicted on various charges stemming from their
    participation in the organization. District Judge Teilborg of
    the United States District Court for the District of Arizona
    presided over the resulting criminal proceedings.
    Velazquez was initially represented by Craig Orent, a
    court-appointed attorney. Orent moved to withdraw and to
    have new counsel appointed on the basis of irreconcilable
    conflict and a breakdown in communications. Velazquez
    then filed a pro se motion requesting the removal of Orent, a
    hearing on that request, and the appointment of substitute
    counsel. After a four-minute hearing in which the district
    court refused Velazquez’s request to speak, the court granted
    counsel’s motion to withdraw. The court then appointed
    Kenneth Countryman to represent Velazquez.
    UNITED STATES V. VELAZQUEZ                  5
    Because the course of Velazquez’s relationship with
    Countryman and the circumstances of her eventual guilty
    plea are central to her arguments on appeal, we recount both
    in detail.
    In September 2013, Ortiz’s counsel filed two motions to
    suppress wiretap evidence.        On Velazquez’s behalf,
    Countryman filed requests to join in each motion. On
    October 1, the court denied all motions to join another
    defendant’s motion to suppress, but allowed the defendants
    to file their own suppression motions within five business
    days. Countryman missed that deadline. On November 8,
    in a motion to extend the deadline, Countryman stated that
    he “did not discover the Court’s Order . . . until recently”
    because he had been in trial. He also filed a motion to
    suppress wiretap evidence and a motion to sever. Later that
    day, the court denied all three motions, and the Government
    offered Velazquez a plea agreement.
    On November 18, 2013, Velazquez filed a pro se request
    for new counsel, arguing that Countryman’s representation
    of her was “beset by failed communications and inexcusable
    inattentiveness.” Specifically, she cited Countryman’s
    failure to file timely pretrial motions despite multiple
    warnings of the deadline from the court and Velazquez
    herself, a breakdown in communications, and an unspecified
    conflict of interest. She also “respectfully request[ed the]
    Court hold a hearing and conduct [an] inquiry into” her
    claims. On November 19, a second superseding indictment
    was issued and Velazquez filed five pro se motions relating
    to discovery, trial timelines, and the court’s jurisdiction.
    On December 3, the district court held a six-minute
    hearing on the pro se motions. After listing the motions,
    6             UNITED STATES V. VELAZQUEZ
    Judge Teilborg stated, “I have reviewed those motions and
    . . . they are denied . . . as lacking any merit whatsoever,”
    and he adjourned the proceeding. The following exchange
    then occurred:
    The Defendant: Excuse me, sir. May I say
    something?
    The Court: I’m sorry?
    The Defendant: May I say something?
    The Court: What is it you wish to say?
    The Defendant: Did you – sorry. I need
    clarification. . . . So basically are you telling
    me that you denied all my motions outright,
    even the request to conduct an inquiry as to
    the conflict of interest with Mr. Ken
    Countryman?
    The Court: I have denied the motions, and I
    went through them one by one, so each of
    them has been denied.
    The Defendant: Okay. So I’m not – there’s
    absolutely no way I can address the Court?
    The Court: I’m sorry?
    The Defendant: There’s – Your Honor, I need
    – I – I – I need to make a record, Your Honor,
    I absolutely need to make a record of his
    failure of communications, the fact that I
    have a plea deadline today and he has failed
    UNITED STATES V. VELAZQUEZ                  7
    to communicate the plea with me. I mean, I
    have evidence upon evidence, I have
    recorded e-mails, calls, everything, Your
    Honor, that he has continuously failed me.
    We have not gone through any of the
    discovery. He’s lied to the Court and told you
    that –
    The Court: I considered everything that was
    in writing that you filed with the Court and
    ruled on them. All right?
    The Defendant: So there’s absolutely nothing
    we can do now, even though he has not met
    with me, he hasn’t done anything.
    The Court: As I said, I reviewed what you put
    in writing and have ruled on it.
    The Defendant: Okay. May I ask another
    thing, Your Honor, please, so I can state this
    on the record? I have a deadline for my plea.
    Okay? Today. If he stays on my case, that
    plea expires at five o’clock. Mr. Ken
    Countryman has never met with me and told
    me anything about the plea, never, Your
    Honor, absolutely never.
    The Court: I’ve taken up the only thing before
    the Court at this time, and he, as your counsel,
    I’m sure, will do what he is obligated to do.
    The Defendant: But he hasn’t done that, Your
    Honor.
    8              UNITED STATES V. VELAZQUEZ
    The Court: Very well.
    Following this hearing, it appears that the prosecution
    granted Velazquez an extension to respond to its proffered
    plea deal. On December 4, Velazquez appeared for
    arraignment on the second superseding indictment before
    Magistrate Judge Bade. As Countryman was stating his
    appearance, Velazquez interjected that she and Countryman
    were “at great odds,” and explained that he had given
    Velazquez only a few minutes to review the indictment, did
    not know what her charges were, and had missed several
    deadlines. Judge Bade responded that she was not going to
    consider those issues because Judge Teilborg had already
    denied Velazquez’s motions, including her motion to
    appoint new counsel. Judge Bade then told Velazquez that
    she could file another motion for new counsel with Judge
    Teilborg and rescheduled the arraignment.
    In accordance with Judge Bade’s suggestion, Velazquez
    filed another motion for new counsel on December 10 and
    requested an evidentiary hearing.           She alleged that
    Countryman had not conducted any independent
    investigation of her case, had not given her access to the
    discovery, and could not answer basic questions about the
    charges against her. She claimed that he repeatedly fell out
    of contact for months at a time, met with her only in public
    places like restaurants, and lied to her about deadlines, when
    she needed to appear in court, and what motions he had filed.
    She asserted that he had filed confidential information
    without her permission.          She further claimed that
    Countryman’s paralegal—a disbarred attorney—“used
    tactics of intimidation, humiliation, and sexual harassment
    to scare her to not go to trial” and told her that he, not
    Countryman, would be the one to file motions on her behalf.
    Finally, she alleged that Countryman had not discussed her
    UNITED STATES V. VELAZQUEZ                   9
    plea offer with her because he said that he had been too busy
    to read it. She concluded that she would be committing
    perjury if she agreed as part of a plea that she had received
    effective representation.
    On December 10, Velazquez appeared before then-
    Magistrate Judge Logan for her rescheduled arraignment.
    The tensions between Velazquez and Countryman were
    evident from the beginning of the hearing. After stating his
    appearance, Countryman said, “Your Honor, I met with my
    client about the indictment. . . . [B]ecause of the nature of
    our communications, I’m not inclined to waive a reading [of
    the indictment] . . . . [W]e’ve been unable to meet and
    communicate and have any kind of productive meeting, and
    the last meeting we had I terminated.” When Velazquez
    tried to bring up her motion for new counsel, Judge Logan
    said:
    The first thing is Judge Teilborg, he’s a senior
    judge in this building, and he’s an Article III
    district judge, and he’s a higher level judge
    than I am. I can’t overrule what he’s already
    done. If he’s already listened or taken
    consideration of the situation as it relates to
    your representation of Mr. Countryman, and
    he’s already ruled on the issue in terms of Mr.
    Countryman being the person that will
    represent you, you can talk for the next two
    hours, and there’s no way for me to change
    anything.
    Judge Logan then explained each of the charges.
    Velazquez indicated that she understood the charges but
    stated that her attorney did not. The judge disagreed: “He
    10            UNITED STATES V. VELAZQUEZ
    understands the nature of your charges, and you certainly
    understand the nature of your charges now.” Although
    Judge Logan observed, “it’s pretty clear to me that you don’t
    wish to plead guilty to anything in this case,” he began to
    address the plea offer.
    Velazquez interjected to raise concerns about her
    counsel. She explained that she had not yet reviewed the
    plea with Countryman. She also alerted Judge Logan that
    she had filed another motion to substitute counsel with Judge
    Teilborg and had attached supporting exhibits. She
    explained that she had recorded her last meeting with
    Countryman “because of our mistrust, because of the
    breakdown in relationship,” and offered the recording as
    proof of her claims.
    Judge Logan declined to review the exhibits or recording
    and instead began explaining that Velazquez would not have
    received a more favorable plea agreement with different
    counsel. He stated that a defense attorney “can’t make the
    executive branch, the federal government, do anything.” He
    added, “If I were standing next to you as a defense counsel,
    it wouldn’t change anything that the U.S. Attorney’s Office
    was willing to do.” The judge went on:
    The Court: So there’s a plea agreement here
    that I’ve received . . . . [W]hen I read through
    the indictment and I read the plea offer, I see
    a few things in here that really popped out.
    And there were agreements, you know, to
    basically dismiss . . . Counts 2, 3, 7, 9, 13, 14,
    26, 27, 28, 29, which led me to believe that
    the United States Government was seeking to
    have you plead guilty to Count No. 1 and
    Count No. 10 of the second superseding
    indictment. What that told me is your lawyer
    UNITED STATES V. VELAZQUEZ                 11
    clearly had some kind of interaction with the
    United States Government because the
    United States Government could have been
    seeking a plea of guilt to everything that’s in
    the indictment. Mr. Vercauteren, what’s her
    exposure if she goes to trial and she’s
    convicted of all of these counts?
    Mr. Vercauteren [the Prosecutor]: She’s
    looking at over 40 years, I would say, pretty
    easily, and that’s I think, under the
    Guidelines, not statutorily. Statutorily she
    could be facing life imprisonment.
    The Court: So she’s facing natural life in
    prison if she’s convicted statutorily. And,
    ma’am, you wouldn’t receive natural life.
    But if the [G]overnment, because what’s
    driving the indictment, you have the
    conspiracy, you have the possessions, the
    money laundering, it’s a lot of time but not as
    much as the big chunks with the drug
    conspiracy. But you have some . . . counts
    involving the guns which push the numbers
    up pretty much. So without getting into the
    actual negotiations, I would assume – and
    correct me if I’m wrong – as part of trying to
    resolve this case, the [G]overnment has
    agreed not to go forward with the [gun]
    counts. Is that right?
    Mr. Vercauteren: That’s correct. Those are
    being dismissed as part of the agreement
    under Section 4A.
    12          UNITED STATES V. VELAZQUEZ
    The Court: And, Mr. Vercauteren, I know
    you’re not Judge Teilborg, but I’m pretty sure
    you have an idea if she pled guilty to this
    offense – And, Mr. Countryman, my
    recollection is your client doesn’t have any
    criminal history; is that right?
    Mr. Countryman: She has zero, Judge.
    The Court: Okay. So –
    Mr. Countryman: She’d be – she should have
    zero points on her criminal history, category
    I.
    The Defendant: I asked him what level I was
    at, and he couldn’t tell me. I asked him what
    is the total amount of the contraband they
    were alleging. He couldn’t tell me. And I
    have that all recorded.
    Mr. Countryman: Well, first of all, Judge,
    anytime somebody sits in front of you and
    puts a bag in front of you, you ought to know
    that they’re surreptitiously recording you, so
    it comes as no surprise. I would be shocked
    that she would submit that to the Court, given
    her behavior during that instance, but that’s
    up to her. I’m sure she probably deleted that
    section.
    The Defendant: It’s all there.
    Mr. Countryman: I told her very clearly
    during that meeting that she was a level 26 to
    UNITED STATES V. VELAZQUEZ                13
    start. We could not get into how far she’d go
    up and down because I’m not going to meet
    with somebody who’s yelling at me.
    ***
    The Court: . . . Well, not every defendant and
    defense lawyer like each other. But I want to
    make sure that you understand something,
    and this is very, very important for you to
    understand. If you don’t like your lawyer and
    if the Judge allows you to get another lawyer,
    it doesn’t mean that your contract changes.
    This is a plea agreement that the executive
    branch is offering you. Okay.
    The Defendant: I –
    The Court: Ma’am, let me just finish. Mr.
    Vercauteren, I’m just going to ask you if she
    for some reason received another lawyer,
    does the plea offer get better?
    Mr. Vercauteren: No.
    The Court: Do you understand that?
    The Defendant: Yes, Your Honor. But the
    thing here is it’s not about us liking each
    other, if he likes me or I don’t like him. The
    point is the record will show, Your Honor,
    that he did not do one thing for my case,
    absolutely not one thing. I mean, he
    defaulted, procedurally defaulted on
    timelines, on the pretrial motion timeline.
    14          UNITED STATES V. VELAZQUEZ
    Over a month, I believe, that’s how late he
    was. And with all due respect, Judge
    Teilborg, I mean I know he’s –
    ***
    The Court: The Article III district judge has
    already decided, whether you enter a plea of
    guilty or you go to trial, Mr. Countryman will
    be standing next to you. Okay? . . . I don’t
    want you to feel pressured in any way,
    because you need to maintain your
    innocence. If you did nothing wrong and the
    marijuana in the house you never saw, the
    bundles in the bathroom, you never saw a
    single firearm, you never saw anything, you
    never did anything, the cameras were wrong,
    it wasn’t you, whatever the situation may be,
    if you feel that you’ve done nothing wrong,
    maintain your innocence and go to trial if
    that’s what’s best for you and your family. I
    want to make sure that you . . . understand
    that the United States Government – it
    doesn’t matter who’s standing there – they’ve
    offered you a disposition that will give you
    an opportunity to enter a plea if you choose
    to.
    The Defendant: Okay.
    The Court: So the fact that Mr. Countryman
    didn’t answer a question about the sentencing
    table, I can answer any question you need to
    know about a sentencing table. . . . But Mr.
    Countryman has been practicing law for a
    UNITED STATES V. VELAZQUEZ                  15
    long, long time. And, ma’am, the things that
    you allege can get a lawyer in a position
    where, you know, they may have some
    difficulty. So I don’t know what happened
    between the two of you, and if you feel the
    need to file another motion with Judge
    Teilborg, I can’t tell you what to do. . . . So,
    ma’am, you seem to think that if you can
    show me that Mr. Countryman is the bad guy
    in terms of he’s not helping you, you get
    another lawyer or this whole thing goes
    away.
    The Defendant: Your Honor, thank you for,
    you know, the information that you’re
    sharing with me, but I’m not here asserting
    that if I get a different attorney, my plea will
    change. That’s not what I’m here to say. . . .
    My issue here is that because of his right to
    effectively assist me or represent me, that’s
    where it’s been a conflict. How can, if he
    really doesn’t know the case, how can he tell
    me or advise me on what’s the best thing to
    do, whether it’s to go to trial or to take the
    plea? My issue about going to trial is that I
    don’t think that he’s going to serve as an
    advocate for me, given his track record.
    Now, the thing about Mr. Ken Countryman
    right from the beginning, we did get
    along. . . . But getting along is one thing.
    Doing something on a case is another thing.
    And this goes back to, you know, the whole
    issue with him not doing anything for me.
    It’s not saying like, oh, I don’t like Mr. Ken
    16          UNITED STATES V. VELAZQUEZ
    Countryman; he’s not getting me a plea that I
    want. That’s not it, Your Honor.
    The Court: Okay. This is where I’m
    confused. How is it that you have – Mr.
    Vercauteren, this plea offer – I think I’ve
    asked before – does this offer get any better?
    If she had three retained lawyers and two CJA
    panel lawyers, does the offer from the United
    States Government get any better?
    Mr. Vercauteren: No.
    The Defendant: And I get that, Your Honor.
    But the thing is it’s such a big range, right,
    from 5 to 40 years – and then it goes into . . .
    is my attorney going to effectively, you
    know, represent me and fight for me and
    make sure that I don’t get that much time?
    That’s what it all plays into. It’s not about the
    plea and not being good enough. And then
    also, about the plea, I have to commit perjury.
    Everything else aside–I’m not going to
    comment on that–I’m only going to comment
    on the fact that I have to–
    The Court: Ma’am, I can tell you right now
    I’m pretty confident that Mr. Countryman
    and Mr. Vercauteren aren’t advocating for
    anyone to come in here and perjure
    themselves and commit a crime, an additional
    crime.
    The Defendant: Okay. And I get that, but in
    the plea it –
    UNITED STATES V. VELAZQUEZ                  17
    The Court: No, no, no, you don’t get that,
    because if you just placed on the record that,
    you know, you would have to commit
    perjury, I would love to hear about that. Who
    asked you to commit perjury?
    The Defendant: No. Sorry. I misspoke. I’m
    sorry. I apologize. What I meant to say is
    that at the end of the plea, it says that I have
    to submit and say I have been . . . that “I am
    satisfied that my defense attorney has
    represented me in a competent manner,” . . .
    I don’t want – I’m scared to go to trial
    because I don’t think that he’s going to, you
    know, put a fight for me. Your Honor, he
    didn’t submit any pretrial motions at all.
    ***
    The Court: . . . This is all I need to know from
    you, ma’am. You’ve been arraigned on the
    second superseding indictment. I’ve also
    informed you of your trial date. Do you wish
    to go forward with the change of plea
    hearing? Yes or no.
    The Defendant: Do I have to have the clause
    in there about my attorney?
    Mr. Vercauteren: Yes. You’re asking me?
    The Court: Yes, you do.         Who are you
    asking?
    The Defendant: Just – I don’t know.
    18            UNITED STATES V. VELAZQUEZ
    The Court: Well, you turned to Mr.
    Vercauteren. That’s part of [Federal Rule of
    Criminal Procedure] 11, ma’am, because you
    have to be satisfied with the representation
    and understand the terms and conditions of
    your plea agreement. But in terms of
    satisfied with the representation, it doesn’t
    mean – There’s – In terms of competent
    representation, it doesn’t mean that Mr.
    Countryman has to look at and touch every
    single aspect of the case. If Mr. Vercauteren
    reached out to Mr. Countryman and said,
    okay, count number one and count number
    ten, which happen to be what we’re seeking
    your client’s guilty plea on, here’s the
    discovery information that directly relates to
    Count 1 and Count 10. If he reviews that,
    that’s a diligent lawyer who’s doing what
    he’s supposed to be doing.
    The court then held a sidebar with the attorneys and
    asked Vercauteren to recount his evidence against
    Velazquez and his negotiations with Countryman that led to
    omitting from the plea a gun charge that would have
    increased her sentence.      Following that sidebar, the
    discussion in open court continued:
    The Court: Ma’am, you have an opportunity.
    Mr. Vercauteren is standing right there in
    front of you. Is there anything you would like
    to ask of him?
    The Defendant: Why is it the fact that even if
    I’m willing to take the plea, that clause about
    him, about my attorney? Why do I have to
    UNITED STATES V. VELAZQUEZ                 19
    submit to the fact that he competently, you
    know, advised me in the matter? . . .
    The Court: Rule 11, there’s certain things that
    must happen if a person says I wish to plead
    guilty. As part of Rule 11, you have to
    believe that your lawyer is competent and has
    represented you properly.
    The Defendant: Your Honor, I don’t believe
    that, but at the same time I’m scared to go to
    trial with him because I don’t think that he’s
    going to do me justice.
    The Court: Well, ma’am–and I’m not going
    to advocate in terms of what I believe you
    need to do, because that’s not my role. Only
    you can decide that. But I’ll tell you this. If
    you have videotape and other co-defendants
    or whatever the evidence will show that says,
    yes, ladies and gentlemen, I’m sworn under
    oath, and yes, that lady in the video right
    there, that’s Guadalupe Velazquez, and if the
    [G]overnment says do you see this woman in
    the courtroom, and the witnesses say, yeah,
    she’s right there, whether they’re agents, lay
    witnesses, co-accused, that’s difficult
    evidence to get around. You could be the best
    defense counsel ever, but if there’s a
    videotape and people say yes, the woman
    with the box is Ms. Velazquez, and the box
    contains marijuana or the package contains
    cash money, and yes, that’s her voice on the
    video audio, and she’s talking about
    structuring cash amounts for deposit in an
    20          UNITED STATES V. VELAZQUEZ
    FDIC bank, that’s devastating. But I’m not
    saying that you’ll be convicted, but your
    lawyer’s job is to make sure that you
    understand that if you take that risk and
    ultimately you’re convicted, that’s a lot of
    time. . . .
    Mr. Countryman: And just for the record,
    Judge, I have advised her that if she doesn’t
    take the plea, there will probably be more
    evidence against her that I haven’t received
    yet.
    The Court: Well, ma’am, the only thing I can
    say about that part is Mr. Vercauteren, he just
    stood up and said it’s today or it’s gone.
    There’s no plea after today from what Mr.
    Vercauteren has said, so –
    The Defendant: Is there any way, Your
    Honor, that my attorney and I could have a
    few days so we can, like, go over the plea?
    The Court: What I can do – I can’t give you
    – Well, the [G]overnment has already placed
    on the record that if the plea –
    The Defendant: Can we ask him?
    The Court: If the plea is not placed on the
    record today, they’re withdrawing. Is that
    correct, Mr. Vercauteren?
    The Defendant: Please, can we just have –
    UNITED STATES V. VELAZQUEZ                 21
    Mr. Vercauteren: Judge, I’ve delayed this so
    often. . . . And so she’s had this plea for a
    long time. It’s time to make a decision. . . .
    The Defendant: Well, see, Your Honor, the
    plea was forwarded to me November 8th. My
    attorney and me, we still haven’t met. Like
    we haven’t gone through, okay, what would
    be my corner if we were to go to trial? What
    are the witnesses that he would like to call?
    What can really hurt me? What can go
    against me? And talk about the pros and cons
    of the plea. That’s the only thing that I’m
    asking for, Your Honor. I’m not trying to
    delay anything. Yes, it was forwarded to me
    on November 8th. Have I sat down with my
    attorney and have we really like, delved into
    it? No, we have not. So how can I
    competently sign something which I really
    don’t know anything about because he hasn’t
    advised me to it?
    The Court: Mr. Countryman, I don’t know
    how much of that is lacking, but if she hasn’t
    had a chance to sit down with you and go
    through it –
    Judge Logan then cleared the courtroom of the
    prosecutor and observers. Countryman reported that he had
    tried to advise Velazquez about her Guidelines level and the
    possibility of an exception to a mandatory minimum
    sentence. Countryman also raised mitigating arguments
    about Velazquez’s education and work ethic, and Judge
    Logan responded that “Judge Teilborg would certainly listen
    22           UNITED STATES V. VELAZQUEZ
    to” such arguments at the sentencing stage. The dialogue
    then continued:
    Mr. Countryman: And just for the record, I
    mean, everyone’s agreed to enter a plea but
    Ms. Velazquez. And a lot of these defendants
    who filed these suppression motions entered
    pleas before that hearing because, in my
    opinion, they knew what the result of that was
    going to be. And if they went to hearing, they
    weren’t going to have pleas. So I just want
    the record clear about that. However, I mean,
    she can do what she wants.
    The Defendant: And then –
    Mr. Countryman: She’s smart. She has her
    own PACER account. She understands. And
    if she doesn’t want to plead, I understand.
    But it’s a lot of time she’s looking at, and it’s
    a lot of evidence.
    The Court: Go ahead, ma’am.
    The Defendant: Your Honor, we go back to –
    we just go back to the core of everything. We
    go back to the basis of, you know, I don’t feel
    that Ken has tried to put any work into my
    case. . . . [W]e don’t have any pretrial
    motions in, Your Honor, in respect to my
    case. I have given him leads upon leads upon
    leads that he never followed up with. . . . But
    at the end of the day, Your Honor, the only
    thing I’m asking is, again, I’m not trying to
    delay. It’s just, like, I cannot make a decision
    UNITED STATES V. VELAZQUEZ                   23
    right now. I can’t. I can’t decide whether I’m
    going to sign the plea or go to trial. I just
    can’t right now, Your Honor. I just can’t.
    ***
    Mr. Countryman: She needs to understand
    that Mr. Vercauteren’s very serious about her
    and putting her on trial. He would have no
    problem with her getting 38 to 42 years, none
    whatsoever. The fact that I –
    The Defendant: But what have you done to
    push back, Ken? What have you done to push
    back, with all due respect?
    Mr. Countryman: . . . This is a mountain of
    evidence against her, and the motions that she
    wanted submitted, she filed them. The Judge
    denied them on the merits. She filed them pro
    se.
    ***
    The Court: Ms. Velazquez, is there anything
    else you would like to tell me?
    The Defendant: Your Honor, I just can’t
    competently make a decision whether I want
    to waive the plea. I know that he’s already
    said that. But I don’t really want to go to trial
    because I’m scared, you know. And it is a lot
    of time to face.
    24            UNITED STATES V. VELAZQUEZ
    The Court: 40 years is a lot of time. You’re
    correct. Five years is a lot of time. Any time
    is a lot of time.
    The Defendant: Any time is a lot of time,
    Your Honor. I just can’t make the decision
    right now. I just can’t. I don’t want to say no
    to the plea. I just can’t make the decision.
    Velazquez then conferred with Countryman, who informed
    the judge that Velazquez wanted to take the plea agreement
    but needed more time to make her decision. The prosecutor
    agreed to give Velazquez one more day to review the
    agreement with her counsel. Judge Logan then adjourned
    the change of plea hearing until the next day.
    Judge Logan reconvened the hearing on December 11.
    Without interruption, the judge proceeded with a standard
    plea colloquy, including reading the charges, explaining the
    plea agreement, explaining what rights Velazquez would
    waive by pleading guilty, and asking whether she
    understood. Toward the end of the hearing, Judge Logan
    raised the issue of Velazquez’s satisfaction with her
    attorney.
    The Court: Ma’am, are you fully satisfied
    with all the assistance your lawyer Mr.
    Countryman’s provided you?
    (The defendant and her counsel confer off the
    record.)
    Mr. Countryman: Just one moment, Judge.
    The Court: Of course.
    UNITED STATES V. VELAZQUEZ                  25
    (The defendant and her counsel confer off the
    record.)
    The Court: Ma’am, is there anything else you
    would like to tell me?
    Mr. Countryman: No, Judge, no, there’s – We
    don’t want to address this particular issue. I
    think the question the Court posited had to do
    with counsel, so if the Court could repeat that.
    The Court: Of course. Mr. Countryman, your
    lawyer –
    The Defendant: Yes.
    The Court: – are you fully satisfied with all
    the assistance that he’s provided you?
    The Defendant: Yes.
    The Court: And, ma’am, yesterday that
    wasn’t the case. What’s changed?
    The Defendant: Well, he – Well, I’m going
    to, you know – extended my arm in good faith
    that even though –
    The Court: You extended your arm?
    The Defendant: I meant to say – I meant to
    say –
    Mr. Countryman: I think she’s trying to say
    we had a –
    26          UNITED STATES V. VELAZQUEZ
    The Defendant: Tried to have a fresh start.
    Mr. Countryman: Right. We had a meeting
    yesterday and today and –
    The Defendant: Fresh start.
    Mr. Countryman: – work together and move
    forward –
    The Defendant: Yeah.
    Mr. Countryman: – and try to get the best
    possible outcome at sentencing.
    The Court: So you believe that the extra time
    that you had with Mr. Countryman allowed
    you to sit down with him, and it allowed Mr.
    Countryman to answer the questions you had
    about this document that you’ve had for a
    month?
    The Defendant: Yes.
    The Court: And he’s answered all those
    questions?
    The Defendant: Yes.
    The Court: So you’re fully satisfied with all
    the assistance he’s provided you in your
    case?
    The Defendant: Yes, yes.
    UNITED STATES V. VELAZQUEZ                   27
    The plea agreement contained a waiver of the right to
    appeal. Judge Logan confirmed during the hearing that
    Velazquez understood the appeal-waiver section and that she
    did not have any questions about it.
    On December 13, 2013, without holding any hearing,
    Judge Teilborg denied Velazquez’s December 10 motion for
    new counsel as moot or, in the alternative, on the merits. The
    order stated that the court had reviewed her motion and her
    testimony at the change-of-plea proceeding, “at which she
    admitted she is fully satisfied with all the assistance she has
    received from her counsel.” On January 2, 2014, the district
    court adopted Judge Logan’s recommendation to accept
    Velazquez’s guilty plea.
    On March 14, 2014, Juan Rocha, an attorney Velazquez
    retained, substituted in for Countryman. At the sentencing
    hearing in June, after asking Velazquez “Have you been
    satisfied with your lawyer” and receiving the response “yes,”
    Judge Teilborg imposed a sentence of 121 months. Rocha
    did not at any point try to withdraw Velazquez’s guilty plea.
    II. STANDARDS OF REVIEW
    We review de novo the validity of an appeal waiver.
    United States v. Portillo-Cano, 
    192 F.3d 1246
    , 1249 (9th
    Cir. 1999). We review a denial of a motion for substitution
    of counsel for abuse of discretion. United States v. Reyes-
    Bosque, 
    596 F.3d 1017
    , 1033 (9th Cir. 2010).
    28             UNITED STATES V. VELAZQUEZ
    III. DISCUSSION
    To begin, the Government contends that we should
    dismiss Velazquez’s appeal without reaching the merits
    because she waived her right to appeal as part of the plea
    agreement. We decline to do so.
    “[W]aivers of appeal must ‘stand or fall with the
    agreement of which they are a part.’” United States v.
    Portillo-Cano, 
    192 F.3d 1246
    , 1250 (9th Cir. 1999) (quoting
    United States v. Wenger, 
    58 F.3d 280
    , 282 (7th Cir. 1995)).
    In Portillo-Cano, the defendant challenged “the soundness
    of his plea allocution under Rule 11,” which provides the
    procedure for accepting pleas in criminal cases. 
    Id.
     We
    explained that such an error “goes to the heart of whether his
    guilty plea, including the waiver of appeal, is enforceable.”
    
    Id.
     As a result, we concluded that “we must determine
    whether the plea was valid in order to determine if appeal is
    permitted.” 
    Id.
     Here, Velazquez asserts that Judge
    Teilborg’s denials of her motions to substitute counsel
    constructively denied her the right to counsel, and she also
    challenges Judge Logan’s compliance with Rule 11.
    Because, as explained below, we agree that she was
    constructively denied counsel, we hold that her appeal
    waiver is unenforceable.
    “Where a criminal defendant has, with legitimate reason,
    completely lost trust in his attorney, and the trial court
    refuses to remove the attorney, the defendant is
    constructively denied counsel.” Daniels v. Woodford,
    
    428 F.3d 1181
    , 1198 (9th Cir. 2005) (citing United States v.
    Adelzo-Gonzalez, 
    268 F.3d 772
    , 779 (9th Cir. 2001)). “A
    UNITED STATES V. VELAZQUEZ                    29
    defendant need not show prejudice when the breakdown of
    a relationship between attorney and client from
    irreconcilable differences results in the complete denial of
    counsel.” United States v. Moore, 
    159 F.3d 1154
    , 1158 (9th
    Cir. 1998); see also Perry v. Leeke, 
    488 U.S. 272
    , 280 (1989)
    (‘“[A]ctual or constructive denial of the assistance of
    counsel altogether’ is not subject to . . . prejudice analysis.”
    (quoting Strickland v. Washington, 
    466 U.S. 668
    , 692
    (1984))). Because the Sixth Amendment’s guarantee of
    effective assistance of counsel applies at the plea-bargaining
    stage, Missouri v. Frye, 
    566 U.S. 133
    , 143–44 (2012),
    constructive denial of counsel can occur at that phase just as
    it can at trial. See Appel v. Horn, 
    250 F.3d 203
    , 212 (3d Cir.
    2001).
    To evaluate whether a district court abused its discretion
    in denying a motion to substitute counsel, we consider three
    factors: “(1) the adequacy of the district court’s inquiry;
    (2) the extent of the conflict between the defendant and
    counsel; and (3) the timeliness of defendant’s motion.”
    United States v. Reyes-Bosque, 
    596 F.3d 1017
    , 1033 (9th
    Cir. 2010).
    1.
    With respect to the adequacy of the district court’s
    inquiry, the Supreme Court has emphasized that, in most
    cases, “courts cannot properly resolve substitution motions
    without probing why a defendant wants a new lawyer.”
    Martel v. Clair, 
    565 U.S. 648
    , 664 (2012); see also United
    States v. Musa, 
    220 F.3d 1096
    , 1102 (9th Cir. 2000) (finding
    error where the district court “made no inquiry at all” into
    the request to substitute); United States v. Gonzalez,
    
    113 F.3d 1026
    , 1028–29 (9th Cir. 1997) (holding that the
    trial court abused its discretion by refusing to hold an
    evidentiary hearing on the motion to substitute). Failure to
    30             UNITED STATES V. VELAZQUEZ
    conduct an inquiry is not necessarily an abuse of discretion
    if the trial court has sufficient information to resolve the
    motion. See Martel, 
    565 U.S. at
    664–66; United States v.
    Smith, 
    282 F.3d 758
    , 764–65 (9th Cir. 2002); United States
    v. McClendon, 
    782 F.2d 785
    , 789 (9th Cir. 1986). Even so,
    “[t]here is no question that our case law favors an inquiry
    when a party seeks substitute counsel.” Smith, 
    282 F.3d at 764
    .
    We have held that, “[w]hen a trial court is informed of a
    conflict between trial counsel and a defendant, ‘the trial
    court should question the attorney or defendant privately and
    in depth, and examine available witnesses.’” Daniels,
    
    428 F.3d at 1200
     (quoting United States v. Nguyen, 
    262 F.3d 998
    , 1004 (9th Cir. 2001)). In Adelzo-Gonzalez, for
    example, the district court denied motions to substitute
    counsel despite obvious antagonism between the attorney
    and defendant. 
    268 F.3d at
    777–78. We held that the district
    court had failed to conduct an adequate inquiry into the
    attorney-client relationship and put “too much emphasis on
    the appointed counsel’s ability to provide adequate
    representation.” 
    Id. at 778
    . Similarly, in Moore, the parties
    alerted the court to a conflict on three occasions before the
    court conducted any inquiry. 
    159 F.3d at 1160
    . When the
    court finally inquired, it gave both parties a chance to speak,
    but “made no inquiries to help it understand the extent of the
    breakdown.” 
    Id.
     We found that this inquiry was inadequate
    and that, as a result, the court had failed to identify the
    irreconcilable conflict between the defendant and his
    attorney. 
    Id.
     at 1160–61.
    In cases in which we have held that the adequacy-of-
    inquiry factor was satisfied, the district court typically held
    at least one hearing during which it asked specific questions.
    See Reyes-Bosque, 
    596 F.3d at 1034
    ; United States v.
    UNITED STATES V. VELAZQUEZ                   31
    Mendez-Sanchez, 
    563 F.3d 935
    , 943–44 (9th Cir. 2009);
    United States v. McKenna, 
    327 F.3d 830
    , 843–44 (9th Cir.
    2003); Smith, 
    282 F.3d at 763
    ; United States v. Corona-
    Garcia, 
    210 F.3d 973
    , 977 (9th Cir. 2000).
    Here, Velazquez clearly and consistently raised concerns
    about her representation, and the district court’s response
    was clearly and consistently insufficient. Judge Teilborg
    summarily denied Velazquez’s first motion to replace
    Countryman. When Velazquez tried to present supporting
    evidence and to argue the motion in court on December 3,
    he refused to consider anything beyond Velazquez’s pro se
    written motion. Velazquez said that her plea deadline was
    that day and that her attorney had not yet met with her about
    it. Judge Teilborg replied that Countryman “will do what he
    is obligated to do.” When Velazquez responded that
    Countryman “hasn’t done that,” the judge merely replied,
    “[v]ery well,” and concluded the exchange.
    On December 10, Velazquez filed her second pro se
    motion for new counsel and requested “an evidentiary
    hearing before the Court.” As described above, this motion
    detailed a serious breakdown in the attorney-client
    relationship as well as claims of intimidation and
    harassment. It also attached supporting exhibits, including
    emails documenting Countryman’s failures to respond to her
    inquiries.
    On December 13, Judge Teilborg denied the December
    10 motion for new counsel as moot or, in the alternative, on
    the merits. He held no hearing and made no inquiry into
    Velazquez’s allegations. Instead, he relied on her testimony
    at the December 11 change-of-plea proceeding, “at which
    she admitted she is fully satisfied with all the assistance she
    has received from her counsel.”
    32             UNITED STATES V. VELAZQUEZ
    Velazquez did everything in her power to alert the court
    to her belief that she was receiving inadequate assistance of
    counsel. She filed two motions and supporting exhibits,
    raised her concerns before three judges at three different
    hearings, and was dogged in placing her concerns on the
    record. Despite all of this, the district court never conducted
    any meaningful inquiry into Velazquez’s concerns about her
    counsel or their relationship.
    Because Velazquez previously replaced an attorney
    based in part on a breakdown in communications, the district
    court, upon seeing her motion to replace Countryman, might
    have assumed that the conflicts stemmed from
    unreasonableness on Velazquez’s part. See Mendez-
    Sanchez, 
    563 F.3d at 944
    . But our precedent required at least
    an inquiry into the relationship between Velazquez and
    Countryman. See, e.g., Smith, 
    282 F.3d at 764
    . Given the
    specific, serious allegations that Velazquez had made about
    her counsel, the district court’s lack of any inquiry at all, let
    alone a “meaningful attempt to probe more deeply into the
    nature” of the attorney-client relationship, Adelzo-Gonzalez,
    
    268 F.3d at 778
    , left Velazquez’s right to counsel in
    jeopardy. The “adequacy of the district court’s inquiry”
    factor thus weighs in favor of finding an abuse of discretion.
    Reyes-Bosque, 
    596 F.3d at 1033
    .
    2.
    The second factor we consider is the extent of the
    conflict between the attorney and client. See 
    id.
     We ask
    whether “there was a serious breach of trust and a significant
    breakdown in communication that substantially interfered
    with the attorney-client relationship.” Adelzo-Gonzalez,
    
    268 F.3d at 779
    .
    UNITED STATES V. VELAZQUEZ                  33
    In situations similar to the one presented here, we have
    held that the extent of the conflict warranted granting
    substitution of counsel. In United States v. Williams,
    
    594 F.2d 1258
     (9th Cir. 1979) (per curiam), for example, we
    held that the district court abused its discretion when it
    denied substitution of counsel despite strong evidence of
    irreconcilable conflict between counsel and the defendant.
    
    Id. at 1261
    . There, it was “clear from the transcript that
    client and attorney were at serious odds and had been for
    some time.” 
    Id. at 1259
    . Moreover, the defendant’s
    allegations of a lack of communication were unrefuted and
    “the response of counsel tended to confirm that the course of
    the client-attorney relationship had been a stormy one with
    quarrels, bad language, threats, and counter-threats.” 
    Id. at 1260
    . In Adelzo-Gonzalez, we likewise found an extensive
    conflict where, among other things, the attorney threatened
    to testify against his client, “virtually abandoned his
    representation of [the client] with respect to the motions to
    substitute counsel,” and left him “to make the motions by
    himself, while the appointed counsel took an adversary and
    antagonistic stance.” 
    268 F.3d at 779
    .
    The record here reflects serious breakdowns in
    communication and trust. Before Judge Teilborg on
    December 3, Velazquez asserted that her attorney had not
    advised her on her plea deal, even though the offer was set
    to expire that day. Her December 10 motion before the
    district court contained multiple specific, troubling
    allegations of a breakdown in communications, a failure to
    independently investigate the case, lies about deadlines and
    filings, and intimidation and harassment.
    The transcript of the hearing on December 10 is also
    replete with evidence of a dysfunctional attorney-client
    34              UNITED STATES V. VELAZQUEZ
    relationship. 1   Countryman began the December 10
    arraignment by reporting problems communicating with his
    client. Velazquez described recording their conversations
    out of a lack of trust; Countryman admitted to cutting
    meetings short because Velazquez yelled at him; they openly
    bickered in court. Countryman did not help Velazquez
    present her motions to substitute counsel. At times he
    actually argued against her position by trying to convince the
    magistrate judge that he had adequately advised her. He also
    made gratuitous statements about there being a mountain of
    evidence against her and the fact that the prosecutor would
    have “no problem with her getting 38 to 42 years, none
    whatsoever.”
    There was evidence that a “significant breakdown” in the
    attorney-client relationship had occurred. As a result, the
    “extent of the conflict” factor also weighs in favor of finding
    an abuse of discretion.
    3.
    The third factor we evaluate is the timeliness of the
    defendant’s request to substitute counsel. Reyes-Bosque,
    
    596 F.3d at 1033
    . In this inquiry, the court “balance[s] ‘the
    resulting inconvenience and delay against the defendant’s
    1
    We recognize that Judge Teilborg did not preside over the
    December 10 hearing. In his order denying Velazquez’s December 10
    motion to substitute counsel, however, he cited her testimony at the
    December 11 change-of-plea hearing as support for the denial. In the
    same passage of the December 11 transcript that Judge Teilborg cited,
    the magistrate judge referred to the fact that Velazquez had said on
    December 10 that she was not satisfied with her counsel, and Velazquez
    and Countryman described having tried during meetings on December
    10 and 11 to have a fresh start. These statements should have alerted
    Judge Teilborg that the December 10 hearing contained information
    relevant to ruling on the substitution motion.
    UNITED STATES V. VELAZQUEZ                  35
    important constitutional right.’” Moore, 
    159 F.3d at 1161
    (quoting United States v. D’Amore, 
    56 F.3d 1202
    , 1206 (9th
    Cir. 1995), overruled on other grounds by United States v.
    Garrett, 
    179 F.3d 1143
     (9th Cir. 1999)). This factor must
    always be evaluated in the context of the litigation in
    question, so no precise amount of advance notice is required
    to render a request timely. Compare, e.g., Moore, 
    159 F.3d at 1161
     (holding that attempts to substitute counsel one
    month before trial and then again two weeks before trial
    were timely even when they would have required
    continuances), and D’Amore, 
    56 F.3d at 1206
     (holding that
    an attempt to contact the court ten days before a hearing and
    a motion one day before the hearing were timely), with
    Mendez-Sanchez, 
    563 F.3d at 942
     (holding that a motion two
    weeks before a trial was not timely because trial had already
    been continued twice, “involved significant discovery,” and
    would have required a further continuance). This is in part
    because “sometimes a defendant would be unable to make a
    motion until shortly before trial—such as in a case where a
    defendant realized his or her counsel was not prepared.”
    Mendez-Sanchez, 
    563 F.3d at 942
    .
    Here, Velazquez filed her first motion to substitute
    counsel ten days after it became clear that Countryman had
    defaulted on the pretrial-motion deadline. In the week
    before her plea deadline, she filed another motion and made
    three attempts to argue in court that Countryman had not
    advised her on the plea. She made all of these efforts more
    than a month before the trial.
    Although this was a complex case with voluminous
    discovery that might have required a continuance if new
    counsel were appointed, Velazquez filed her motions
    promptly. The third factor thus also favors holding that the
    district court abused its discretion.
    36               UNITED STATES V. VELAZQUEZ
    4.
    Even if her motions could be considered untimely—a
    reason the district court never relied on in its rulings on the
    motions to substitute—the court’s failure to conduct an
    adequate inquiry and the extent of the conflict outweigh any
    untimeliness in the balance of factors. Taken together, the
    factors weigh in favor of finding an abuse of discretion. We
    thus conclude that the district court abused its discretion by
    denying Velazquez’s requests to substitute counsel without
    conducting an adequate inquiry.          The result was a
    constructive denial of counsel that requires us to vacate
    Velazquez’s guilty plea. 2 See Perry, 
    488 U.S. at 280
    ;
    Moore, 
    159 F.3d at 1158
    .
    The Government argues against this result, asserting that
    any concerns Velazquez had about her counsel were
    remedied by meetings she had with him on December 10 and
    11. The Government points out that Velazquez stated during
    the December 11 change-of-plea hearing that she had
    resolved the problems with her counsel during those
    meetings. Even if meetings the day before a plea hearing
    could potentially remedy serious and longstanding
    2
    In contrast to Musa, in which there was no record on the nature of
    conflict, 
    220 F.3d at 1099
    , 1102–03, here we have substantial
    information regarding Velazquez’s concerns about her counsel. As a
    result, unlike in Musa, it is unnecessary for us to remand for a further
    inquiry into Velazquez’s concerns before deciding whether her guilty
    plea should be vacated. In any event, the Government has not argued
    that vacatur of the plea is inappropriate if Velazquez succeeds on her
    substitution-of-counsel claim, and any argument to that effect is
    therefore waived.
    UNITED STATES V. VELAZQUEZ                         37
    breakdowns in an attorney-client relationship in a
    complicated case—a question we need not decide—we do
    not believe that Velazquez’s statements at the December 11
    hearing are a reliable indication that productive meetings
    between Velazquez and her counsel had occurred. As
    explained below, we think it is likely that her statements
    instead were caused by the magistrate judge’s discussion of
    the plea the day before. 3 See United States v. Anderson,
    
    993 F.2d 1435
    , 1438 (9th Cir. 1993) (explaining that when a
    judge improperly participates in a plea negotiation, the
    defendant’s “responses to the judge’s questioning during the
    formalistic colloquy do not allay our concerns regarding
    voluntariness”), abrogated on other grounds by United
    States v. Davila, 
    133 S. Ct. 2139
     (2013).
    Federal Rule of Criminal Procedure 11(c)(1) prohibits
    any participation by a judge in plea negotiations. See United
    States v. Bruce, 
    976 F.2d 552
    , 555–56 (9th Cir. 1992),
    abrogated on other grounds by Davila, 
    133 S. Ct. 2139
    .
    This includes magistrate judges even when they are neither
    “the sentencing judge nor the judge presiding over the
    defendant’s criminal case.” United States v. Myers, 
    804 F.3d 1246
    , 1253 (9th Cir. 2015). One of the reasons for Rule 11’s
    ban on judicial participation in plea discussions is to avoid
    the “high and unacceptable risk of coercing a defendant to
    accept the proposed agreement and plead guilty.” Bruce,
    
    976 F.2d at 556
    .
    3
    Because we have concluded that Velazquez’s plea must be vacated
    on Sixth Amendment constructive-denial-of-counsel grounds, we need
    not address the Government’s arguments that any Rule 11 violation is
    subject to plain error review, and that Velazquez has failed to show
    sufficient prejudice to meet that standard. We address Rule 11 only to
    respond to the Government’s argument that her statements on December
    11 indicated that the constructive denial of counsel had been remedied.
    38             UNITED STATES V. VELAZQUEZ
    In Bruce, for example, we were concerned that the
    judge’s involvement, even though well-intentioned, carried
    an undue risk of coercion. 
    Id. at 556, 558
    . In that case, the
    judge asked the prosecutor to summarize the plea offer and
    state the range of possible sentences based on the charges.
    
    Id. at 555
    . After confirming that the defendants understood
    they were facing a possible life sentence if they proceeded
    to trial, the judge asked them, “You don’t want to think about
    that some more, the two of you?” 
    Id.
     He continued, “I
    would think seriously about it, both of you. Life in prison is
    a long time. It is really nothing to play with.” 
    Id.
     We
    observed that the judge’s comments made “unambiguously
    clear [his] preference that the defendants accept the plea
    bargain and plead guilty,” despite the fact that the judge
    never explicitly advised the defendants to do so. 
    Id.
     at 556
    n.2. We emphasized that any judicial involvement in plea
    discussions carries an “unacceptably high risk of coercion.”
    
    Id. at 556
    .
    It is this risk that leads us to treat Velazquez’s statements
    at the December 11 hearing as unreliable. Even after
    explicitly recognizing that Velazquez was disinclined to
    plead guilty, Judge Logan proceeded for over an hour to
    effectively urge acceptance of the plea deal. He repeatedly
    asserted that the Government would not change the terms of
    its offer if Velazquez received a new lawyer. He elicited
    comments from the prosecutor on the deal’s advantages. He
    emphasized that Judge Teilborg had already decided that
    Countryman would be her attorney should she go to trial and
    tried to assuage her concerns about his performance. Judge
    Logan speculated that the evidence against her at trial could
    be “devastating,” but that, if she pleaded guilty, Judge
    Teilborg would be receptive to arguments that would shorten
    her sentence. And, finally, when Velazquez asked why the
    plea agreement required her to agree that she was satisfied
    UNITED STATES V. VELAZQUEZ                         39
    with her attorney, Judge Logan answered that Rule 11
    required it. 4 Although Judge Logan periodically stated that
    he was not interfering with the parties’ negotiations or
    advising Velazquez what to do, the full picture that
    Velazquez must have taken away from the December 10
    hearing is apparent: the only way to avoid facing a mountain
    of devastating evidence at trial with an attorney she did not
    trust was to plead guilty, and to plead guilty she must attest
    that she was satisfied with her attorney. 5
    As a result, Velazquez’s two meetings with her attorney
    after the December 10 hearing and her “responses to the
    judge’s questioning during the formalistic colloquy” on
    December 11 affirming her satisfaction with her attorney “do
    not allay our concerns.” See Anderson, 
    993 F.2d at 1438
    .
    We conclude that there is a substantial risk that Velazquez
    agreed that she was satisfied with her attorney’s performance
    because the magistrate judge pressured her to accept the plea
    and she knew that she had to make that statement to enter the
    plea. Her December 11 statement thus does not undermine
    4
    Of course, we do not fault the magistrate judge for accurately
    responding to Velazquez’s question about Rule 11. We include this
    because it is an important part of the message that Velazquez received.
    5
    The Government suggests that the fact that a day passed between
    the December 10 hearing and her December 11 plea allowed any
    coercion to dissipate. We disagree. See United States v. Sanya, 
    774 F.3d 812
    , 818, 822 (4th Cir. 2014) (finding a Rule 11 violation where plea
    changed five days after Rule 11 violation); Anderson, 
    993 F.2d at
    1438–
    39 (finding a Rule 11 violation where plea changed two days after
    violation); Bruce, 
    976 F.2d at
    554–56 (finding a Rule 11 violation where
    plea changed day after violation).
    40               UNITED STATES V. VELAZQUEZ
    our conclusion that the denial of Velazquez’s motion to
    substitute counsel was an abuse of discretion. 6
    IV. CONCLUSION
    For the foregoing reasons, we VACATE Velazquez’s
    convictions and REMAND for further proceedings.
    KOZINSKI, Circuit Judge, concurring:
    I join Judge Friedland’s thorough opinion without
    reservation. I write only to note that the judges below acted
    with what they believed to be Velazquez’s best interest at
    heart. Even now, withdrawing from the plea may not be
    wise, but it’s Velazquez’s choice to make. I hope and trust
    that the government will accept her choice with generosity
    and compassion.
    6
    The transcript of the hearing on December 11 and Velazquez’s
    actions after it serve only to strengthen this assessment. On December
    11, when Judge Logan asked whether Velazquez was satisfied with her
    attorney, she hesitated to respond. She and Countryman conferred off
    the record. He then said, “We don’t want to address this particular
    issue.” When the judge asked her again, Velazquez said she was
    satisfied. But only two months later, a privately retained attorney
    substituted in for Countryman. Taken together, these facts suggest that
    Velazquez was not, in fact, satisfied with Countryman’s performance.
    

Document Info

Docket Number: 14-10311

Citation Numbers: 855 F.3d 1021

Filed Date: 5/1/2017

Precedential Status: Precedential

Modified Date: 1/12/2023

Authorities (23)

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United States v. Rupert Earl McClendon United States of ... , 782 F.2d 785 ( 1986 )

United States v. Trung Tran Nguyen , 262 F.3d 998 ( 2001 )

United States v. Francisco Alonso Portillo-Cano , 192 F.3d 1246 ( 1999 )

United States v. Reyes-Bosque , 596 F.3d 1017 ( 2010 )

United States v. Benjamin Corona-Garcia , 210 F.3d 973 ( 2000 )

United States v. Carlos Adelzo-Gonzalez , 268 F.3d 772 ( 2001 )

United States v. Carl Dexter Moore , 159 F.3d 1154 ( 1998 )

United States v. Michael Andrew Smith, AKA the Bird , 282 F.3d 758 ( 2002 )

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United States v. Drago Carl Musa , 220 F.3d 1096 ( 2000 )

United States v. Mark Roy Anderson , 993 F.2d 1435 ( 1993 )

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United States v. Kenneth R. Bruce , 976 F.2d 552 ( 1992 )

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