United States v. Jeremy Outland ( 2021 )

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 20-1160
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
JEREMY OUTLAND,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Central District of Illinois.
No. 3:17-cr-30073 — Sue E. Myerscough, Judge.
____________________
ARGUED JANUARY 22, 2021 — DECIDED APRIL 14, 2021
____________________
Before RIPPLE, KANNE, and SCUDDER, Circuit Judges.
SCUDDER, Circuit Judge. Shortly after police arrested him
for suspected drug dealing, Jeremy Outland overdosed on
heroin and fell unconscious. The officers brought Outland to
a local hospital where, after receiving care, he agreed to talk
to the police, received Miranda warnings, and made several
incriminating statements which led to federal charges for dis-
tributing heroin. Outland moved to suppress his statements,
arguing that he was in no condition at the hospital either to
2 No. 20-1160
knowingly and intelligently waive his Miranda rights or to
otherwise give voluntary statements to the police.
The district court denied Outland’s motion, finding that
his statements were voluntary. At no point, though, did the
district court analyze or answer whether Outland knowingly
and intelligently waived his Miranda rights. The questions are
not one and the same: to the contrary, whether a defendant
knowingly and intelligently waived his rights at the outset of
a police interview is a distinct and separate inquiry from
whether, in the circumstances of the interview as a whole, the
defendant’s statements were voluntary. Given that Outland
was unconscious and entirely incapacitated from an overdose
just two hours before police questioned him, a finding on the
former question matters. We therefore remand for the district
court to make a determination on the validity of Outland’s
Miranda waiver in the first instance.
I
A
Hoping to stem the swelling tide of heroin use in Spring-
field, Illinois, the city’s police department opened an investi-
gation in 2017 to root out heroin traffickers. As part of this in-
vestigation, police arrested Jeremy Outland mid-morning in
November 2017 for selling heroin. The officers placed Out-
land in a squad car and planned to bring him to the local Drug
Enforcement Agency office for questioning. But on the way,
and somehow while handcuffed, Outland consumed what he
claimed was 3.5 grams of heroin he managed to hide from the
police. One of the officers then noticed that Outland had col-
lapsed in the back seat, observed a white powder covering his
face and jacket, and rerouted to a nearby emergency room.
No. 20-1160 3
Outland was unresponsive upon arrival at 10:44 a.m., requir-
ing doctors to administer multiple medications to treat the
heroin overdose.
Outland regained consciousness around 10:51 a.m. but fell
back into an unresponsive state around 11:10 a.m. and again
around 11:20 a.m. despite receiving additional doses of med-
ication in the intervals. He then experienced several apneic
episodes where he would temporarily stop breathing while
asleep. Eventually doctors placed Outland on a continuous
medication drip at 12:25 p.m. and made plans to transfer him
to the intensive care unit.
Around 1:00 p.m.—slightly over two hours after Outland
first arrived unconscious in the ER—Daniel Weiss, a narcotics
officer with the Springfield Police Department, came to the
hospital to speak with Outland. Officer Weiss began by read-
ing Miranda warnings and Outland agreed to talk. Over the
span of a 45-minute interview, Outland made several incrim-
inating statements about his heroin dealing between Chicago
and Springfield.
B
Federal charges followed for distributing and conspiring
to distribute 100 grams or more of heroin, in violation of
21 U.S.C. §§ 841(a)(1), 841(b)(1)(B)–(C), 846. Outland later
moved to suppress the statements he made to Officer Weiss
as well as other evidence obtained by police not relevant to
his appeal. Outland advanced the twofold contention that he
“was so intoxicated as to render his statement involuntary”
and that “he was unable to voluntarily and knowingly waive
his Miranda rights based upon a long list of medications he
was under at the time.” In the argument section of his motion,
4 No. 20-1160
Outland similarly contended that “[w]here the evidence
plainly shows that a suspect is so grossly intoxicated that he
no longer has the capacity to knowingly waive his rights, sup-
pression of any resulting statement is warranted.”
The district court held an evidentiary hearing, received
testimony from Officer Weiss, Outland, and a DEA agent, and
ultimately issued an order denying Outland’s motion. In the
course of its ruling, the district court summarized Outland’s
testimony that he did not recall waiving his rights and was
under the influence of drugs during the interview. The court
also recounted Officer Weiss’s contrary impressions of Out-
land’s mental state—that Outland was coherent, had re-
quested to speak with law enforcement, and, despite appear-
ing under the influence of heroin, never lost consciousness
during the interview.
Yet the district court made no determination that Outland
knowingly and intelligently waived his Miranda rights at the
outset of his interview with Officer Weiss. The court instead
disposed of the motion by focusing exclusively on the volun-
tariness of the statements. In a very brief analysis, spanning
just over a page, the court underscored that it found no evi-
dence of police coercion during the interview and that it cred-
ited Officer Weiss’s testimony that Outland had asked to
speak with law enforcement—a fact tending to show volun-
tariness. The court concluded that, regardless of whether Out-
land was intoxicated from heroin or hospital-administered
medication, his statements were voluntary.
Having failed to suppress any of the government’s evi-
dence against him, Outland entered a conditional guilty plea
to both counts in the indictment but reserved the right to ap-
peal the denial of his suppression motion. The district court
No. 20-1160 5
imposed a below-guidelines sentence of 108 months followed
by four years of supervised release.
Outland now appeals the district court’s denial of his sup-
pression motion.
II
A
We review a district court’s denial of a motion to suppress
under a dual standard, assessing conclusions of law de novo
and evaluating factual findings for clear error with special
deference granted to the court’s credibility determinations.
See United States v. Nichols, 847 F.3d 851, 856–57 (7th Cir.
2017).
A defendant’s challenge to the admission of statements
made during a custodial interrogation presents two separate
questions: whether he received and validly waived his Mi-
randa rights, and whether his statements themselves were vol-
untary. See Missouri v. Seibert, 542 U.S. 600, 608–09 (2004);
Dickerson v. United States, 530 U.S. 428, 444 (2000) (“The re-
quirement that Miranda warnings be given does not, of course,
dispense with the voluntariness inquiry.”); Henderson v. De-
Tella, 97 F.3d 942, 946 (7th Cir. 1996).
The first question stems from the obligation that law en-
forcement, at the outset of a custodial interrogation, convey
Miranda warnings—a prophylactic requirement designed to
safeguard a suspect’s Fifth Amendment privilege against self-
incrimination—and secure a waiver of those rights. See Mi-
randa v. Arizona, 384 U.S. 436, 467 (1966); Dickerson, 530 U.S. at432–35 (recounting the historical development of the Miranda
rule). A defendant can waive his Miranda rights and agree to
speak to the authorities as long as the waiver is “the product
6 No. 20-1160
of a free and deliberate choice rather than intimidation, coer-
cion, or deception” and is made knowingly and intelligently,
“with a full awareness of both the nature of the right being
abandoned and the consequences of the decision to abandon
it.” Moran v. Burbine, 475 U.S. 412, 421 (1986).
The second question is broader and asks whether, in the
totality of the circumstances, the defendant’s statements to
authorities were voluntary. See Mincey v. Arizona, 437 U.S.
385, 398 (1978) (“[A]ny criminal trial use against a defendant
of his involuntary statement is a denial of due process of
law.”). A confession will be deemed involuntary if police ob-
tained the statement through coercive means that overcame
the defendant’s free will. See Colorado v. Connelly, 479 U.S. 157,
164–65 (1986).
These two inquiries are deliberately distinct. Indeed, “Mi-
randa’s procedural safeguards exist,” the Supreme Court has
emphasized, “precisely because the voluntariness test is an
inadequate barrier when custodial interrogation is at stake”
for ensuring that inculpatory statements admitted as evidence
were the product of free choice. J.D.B. v. North Carolina,
564 U.S. 261, 281 (2011). Putting these two questions together,
“a valid waiver of Miranda rights is necessary before a custo-
dial statement may be admitted,” but is not sufficient because
“a statement may still be found involuntary under the totality
of the circumstances even though the waiver was valid.”
United States v. LeShore, 543 F.3d 935, 941 (7th Cir. 2008); see
also Miller v. Fenton, 474 U.S. 104 (1985) (recognizing that co-
ercive interrogation techniques may have rendered a confes-
sion involuntary notwithstanding a valid Miranda waiver).
Likewise, the failure to comply with Miranda’s prescription
may require the exclusion of incriminating custodial
No. 20-1160 7
statements that are otherwise voluntary. See Oregon v. Elstad,
470 U.S. 298, 306–07 (1985). In the end, then, the prosecution
must prove both a valid Miranda waiver and the voluntariness
of the resulting confession by a preponderance of the evi-
dence. See Seibert, 542 U.S. at 608 n.1.
B
Outland’s motion to suppress raised both of these ques-
tions. He contended that, given his severe state of drug intox-
ication upon arriving at the hospital, he was unable to know-
ingly waive his Miranda rights when he agreed to speak with
Officer Weiss. Outland separately maintained his subsequent
statements were involuntary. To be sure, Outland could have
included a more fulsome argument to address how the heroin
or hospital-administered medications impacted his ability to
understand and waive his Miranda rights at the outset of the
interview with Officer Weiss. But we are satisfied, and the
government agreed at oral argument, that Outland ade-
quately raised challenges before the district court to both the
knowing and intelligent nature of his waiver and to the vol-
untariness of his statements.
On appeal Outland focuses only on the Miranda waiver,
without renewing the contention that his statements them-
selves were involuntary. So we focus our review only on the
sufficiency of Outland’s Miranda waiver.
C
What concerns us is what is missing from the district
court’s findings. The court’s analysis, in a mere three para-
graphs, found that Outland’s statements over the course of his
encounter with Officer Weiss were voluntary and not the
8 No. 20-1160
product of police coercion. We have no issue with that find-
ing, and Outland does not press any challenge in that respect.
But nowhere in its order did the district court make any
finding as to whether Outland knowingly and intelligently
waived his Miranda rights before the interview began—a
point the government candidly recognized at oral argument.
Nothing in the court’s order leads us to presume that the court
necessarily or implicitly made such a determination. Cf., e.g.,
United States v. Combs, 222 F.3d 353, 362 (7th Cir. 2000) (over-
looking the lack of an explicit finding that police read a sus-
pect his Miranda rights where such a finding was implicit in
the court’s order). On the contrary, the district court seemed
to assume Outland’s intoxication was irrelevant in light of the
court’s finding of no police coercion—but the mere fact “that
a Miranda warning was given and the accused made an unco-
erced statement” to police “is insufficient to demonstrate a
valid waiver of Miranda rights.” Berghuis v. Thompkins,
560 U.S. 370, 384 (2010). “The prosecution must make the ad-
ditional showing that the accused understood these rights.”
Id.Remember the events leading to Outland’s police inter-
view. He overdosed on heroin, awoke in an emergency room,
and lapsed in and out of consciousness as the medical team
administered several rounds of drugs. Less than two hours
later, Officer Weiss arrived to speak with him. In these circum-
stances, and given the potential that Outland’s mental and
physical state may have impacted his comprehension of his
Miranda rights, the district court’s failure to make a finding
that Outland’s waiver was knowing and intelligent represents
a material omission.
No. 20-1160 9
The government invites us to overlook the gap. It points
to exhibits and portions of testimony from the suppression
hearing and specific segments of the interview recording to
show that Outland was alert, responsive, coherent, and of
sound mind when the colloquy with Officer Weiss began. The
totality of circumstances, the government maintains, demon-
strates that Outland understood his Miranda rights and know-
ingly waived them—regardless of any heroin or medication
in his system.
Maybe. But maybe not. We hesitate because the district
court did not make any such determination, and we are reluc-
tant to make this necessary factual finding for the first time on
appeal. Miranda has been on the books since 1966. But in the
subsequent 55 years, we have found not one example, nor has
the government identified any, of our court making a finding
in the first instance that a defendant knowingly and intelli-
gently waived his rights. For good reason. The “resolution of
a motion to suppress is almost always a fact-specific inquiry,
and it is the district court which heard the testimony and ob-
served the witnesses at the suppression hearing.” United
States v. Terry, 915 F.3d 1141, 1144 (7th Cir. 2019). Sitting in
review as a court of appeals, we lack the benefit of evaluating
Outland’s credibility and demeanor in person or comparing
Outland’s testimony against Officer Weiss’s version of events.
District courts are much better suited to undertake these
tasks. “While we largely read briefs for a living, they largely
assess the credibility of parties and witnesses for a living.”
June Med. Servs. L.L.C. v. Russo, 140 S. Ct. 2103, 2141 (2020)
(Roberts, C. J., concurring) (quoting Taglieri v. Monasky,
907 F.3d 404, 408 (6th Cir. 2018) (en banc)); see also DeMarco
v. United States, 415 U.S. 449, 450 n.* (1974) (“[F]actfinding is
10 No. 20-1160
the basic responsibility of district courts, rather than appellate
courts.”).
D
A suspect’s waiver of his Miranda rights, and the resulting
admissibility of his incriminating statements, often have
grave consequences for individual liberty. It is the confluence
of two considerations that motivates our concern in this case:
the fact pattern involving a hospital-setting interrogation of a
recently resuscitated man, and the district court’s failure to
make any assessment of whether he was capable, in his con-
dition, of knowingly and intelligently waiving his Miranda
rights. We are reluctant to make the call ourselves or to deem
the district court’s analysis close enough.
It may be that the totality of the facts demonstrates that
Outland understood his rights and the consequences of their
abandonment when he agreed to talk to Officer Weiss. But it
falls within the district court’s competency to make such a de-
termination in the first instance. See Pullman-Standard v.
Swint, 456 U.S. 273, 291 (1982) (“When an appellate court dis-
cerns that a district court has failed to make a finding because
of an erroneous view of the law, the usual rule is that there
should be a remand for further proceedings to permit the trial
court to make the missing findings.”). Because the district
court did not resolve whether Outland knowingly and intelli-
gently waived his Miranda rights, we remand for the limited
purpose of allowing the district court to make such a determi-
nation. “Absent a compelling reason otherwise, [this] deter-
mination[] should be based on the existing record and limited
to the testimony and other evidence already presented.”
United States v. Fields, 371 F.3d 910, 917 (7th Cir. 2004).
No. 20-1160 11
We therefore REMAND for further proceedings consistent
with this opinion.