United States v. Jones

20-3009
United States v. Jones
UNITED STATES COURT OF APPEALS
FOR THE SECOND CIRCUIT
August Term 2021
(Argued: September 17, 2021 Decided: August 1, 2022)
No. 20-3009
––––––––––––––––––––––––––––––––––––
UNITED STATES OF AMERICA,
Appellee,
-v.-
DAVID ROY JONES,
Defendant-Appellant.
––––––––––––––––––––––––––––––––––––
Before: LIVINGSTON, Chief Judge, CHIN and NARDINI, Circuit Judges.
Defendant-Appellant David Roy Jones was indicted for knowingly produc-
ing child pornography in violation of federal law. He moved to suppress evidence
gathered from his electronic devices, arguing that the government’s search war-
rants lacked probable cause and therefore violated his Fourth Amendment rights.
The United States District Court for the Western District of New York (Feldman,
M.J. & Larimer, J.) denied the motion. Jones then pleaded guilty but reserved the
right to appeal the district court’s decision on his motion to suppress.
1
We disagree with the district court that Jones’s prior guilty plea to an earlier
charge in Tennessee state court precludes him from challenging the search war-
rants in this case. But we agree that, even assuming arguendo that the warrants are
defective, the good-faith exception to the exclusionary rule applies. We therefore
AFFIRM the judgment of the district court.
FOR APPELLEE: TIFFANY H. LEE, Assistant United States At-
torney, for James P. Kennedy, Jr., United
States Attorney for the Western District of
New York, Buffalo, NY.
FOR DEFENDANT-APPELLANT: JAY OVSIOVITCH, Assistant Federal Public
Defender, Federal Public Defender’s Office,
Western District of New York, Rochester,
NY.
2
DEBRA ANN LIVINGSTON, Chief Judge:
Defendant-Appellant David Roy Jones (“Jones”) appeals from an August
31, 2020 judgment of the United States District Court for the Western District of
New York (Larimer, J.), convicting him of the knowing production of child por-
nography and sentencing him to a term of imprisonment of 240 months and a 10-
year term of supervised release. Jones pleaded guilty pursuant to a plea agree-
ment but reserved the right to appeal the district court’s denial of his suppression
motion. On appeal, Jones challenges the district court’s determinations that (1) his
earlier guilty plea in Tennessee state court precludes him from challenging the va-
lidity of search warrants issued in Tennessee; and (2) even assuming the warrants
are defective, the good-faith exception to the exclusionary rule applies.
As explained below, we conclude that the district court erred by precluding
Jones from challenging the Tennessee warrants and the use of any evidence de-
rived from those warrants. At the same time, we agree with the district court that
even assuming arguendo that the warrants are defective, the exclusionary rule does
not apply here. We therefore affirm the district court’s judgment.
3
BACKGROUND
I. Factual Background 1
A. The Tennessee Investigation
The Hamblen County, Tennessee Sheriff’s Office (the “Sheriff’s Office”) be-
gan investigating Jones in 2016 when it received information that he had taken
pornographic photographs of two minors—one 17 years old (“State Victim 1”) and
the other 15 years old (“State Victim 2”). State Victim 1’s mother (“Complainant”)
alleged that Jones gave the victims alcohol and drugs, took nude pictures of them,
and made sexual advances toward them. She also attested that she had seen a text
message from Jones in which he requested nude photographs from her daughter.
That same day, the Sheriff’s Office received signed statements from each
victim describing Jones’s behavior. State Victim 1 alleged that Jones gave her and
State Victim 2 drugs and alcohol and took nude pictures of them. She also alleged
that Jones kept nude pictures of her on his phone. And she alleged that Jones often
made sexual remarks, including repeatedly asking to perform oral sex on State
Victim 2.
1 The facts are not in dispute and are derived from evidence the parties presented
regarding Jones’s motion to suppress, the magistrate judge’s report and recommendation
addressing Jones’s motion to suppress, and the district court’s subsequent decision and
order denying Jones’s motion to suppress.
4
State Victim 2 made similar allegations. She alleged that Jones plied her and
State Victim 1 with drugs and alcohol. She also alleged that Jones asked them to
pose nude for him on a bed so he could take photographs of them. And she added
that Jones often made sexual remarks directed at her, echoing State Victim 1’s al-
legation that Jones asked repeatedly to perform oral sex on her.
Based on these allegations, Detective Sergeant Jim Brooks (“Detective
Brooks”) sought and obtained six separate warrants (“Tennessee Warrants”).
These warrants authorized the Sheriff’s Office to seize and search Jones’s property
for evidence that he sexually exploited a minor in violation of Tennessee law. See
Tenn. Code Ann. § 39-17-1003.
Detective Brooks first sought a warrant to seize Jones’s cellular devices. In
an affidavit submitted in support of his application for the first warrant, Detective
Brooks attested:
[The] listed cellular device[] or devices in the possession
of David Ray [sic] Jones at [Jones’s address] were used to
take pictures of minor children. On June 28, 2016[,]
[K.B.], the mother of 17 year old minor child [State Victim
1] reported that on or about January 1, 2016 to June 28,
2016[,] David Ray Jones . . . did make sexual advances to-
wards her daughter. [K.B.] also stated that David Ray
Jones . . . got her daughter and her friend [State Victim
2], 15 years old, drunk and high[,] took nude pictures of
them, and made sexual advances towards [them].
5
ECF No. 25-1 at 7. 2 Based on his knowledge, training, and experience, Detective
Brooks attested that he believed that the devices would “contain evidence of pic-
tures of minor children in different stages of undress.” Id. at 8. After Tennessee
Criminal Court Judge John Dugger (“Judge Dugger”) granted the application, De-
tective Brooks executed the warrant.
Detective Brooks applied for two more warrants to search Jones’s home and
vehicles for electronic devices the next day. Detective Brooks submitted similar
affidavits in support of the applications for these warrants. Judge Dugger granted
the applications, and the Sheriff’s Office executed both warrants. Detective Brooks
recovered photographs and other electronic devices from Jones’s residence.
Detective Brooks later obtained three more warrants that authorized him to
search the electronic devices the Sheriff’s Office had seized. The final application
explained that Detective Brooks had “learned of the existence of a third victim”—
Jones’s “ex stepdaughter from New York”—and that there was “reason to believe
that photos of [her were] stored on the laptop computer, hard drive, and memory
cards” the Sheriff’s Office had recovered. Id. at 29.
2 Citations to “ECF” are to the district court’s docket, No. 18-cr-6061 (DGL) (JWF).
6
Jones pleaded guilty to two counts of Sexual Exploitation of a Minor in
Hamblen County Criminal Court in July 2017. Tennessee first charged Jones with
possessing more than 50 pornographic images, a Class C felony under Tennessee
law that is punishable by three to fifteen years’ imprisonment. See Tenn. Code
Ann. § 39-17-1003(a), (b); id. § 40-35-111. But Jones pleaded guilty to possessing
fewer than 50 images, a Class D felony punishable by only two to twelve years’
imprisonment. See id. § 39-17-1003(d); id. § 40-35-111. Judge Dugger sentenced
Jones to serve two years in prison.
B. The Federal Investigation
Federal law enforcement started investigating Jones in 2017 when a different
victim (“Federal Victim 1”), who resided in the Western District of New York, con-
tacted the Federal Bureau of Investigation (“FBI”). Federal Victim 1 alleged that
Jones had taken nude pictures of her when she was between 13 and 16 years old.
An FBI agent contacted Detective Brooks, who provided two pornographic pho-
tographs obtained from Jones’s residence through the state investigation. Federal
Victim 1 confirmed that the photographs depicted her and alleged that Jones took
them when she was about 14 years old.
7
The FBI obtained two search warrants (the “Federal Warrants”), authorizing
it to search electronic devices previously collected by the Sheriff’s Office. The
Sheriff’s Office sent the FBI digital copies of three storage cards seized from Jones’s
residence. Those storage cards contained pornographic pictures and videos of two
minors. Federal Victim 1 confirmed that these pictures and videos depicted her
and a minor male (“Federal Victim 2”). She claimed that she and Federal Victim 2
took the pictures at Jones’s direction and that Jones took the videos.
II. Procedural History
A federal grand jury indicted Jones on two counts of Production of Child
Pornography in 2018. See 18 U.S.C. § 2251(a). The government later filed a notice
of its intent to use evidence seized under the Tennessee and Federal Warrants. See
Fed. R. Crim. P. 12(b)(4). Jones moved to suppress. He argued that the Tennessee
Warrants violated the Fourth Amendment’s particularity and probable cause re-
quirements and that the evidence seized under the Federal Warrants was fruit of
the poisonous tree.
In a report and recommendation, Magistrate Judge Jonathan Feldman rec-
ommended that the district court deny Jones’s motion. United States v. Jones (R&R),
2019 U.S. Dist. LEXIS 101810 (W.D.N.Y. Apr. 11, 2019). Relying largely on this
8
Court’s decision in United States v. Gregg, 463 F.3d 160 (2d Cir. 2006) (per curiam),
Judge Feldman reasoned that Jones’s guilty plea in Tennessee state court “collat-
erally estopped” him from challenging the constitutional validity of the Tennessee
Warrants. Id. at *5–11. The district court adopted Judge Feldman’s recommenda-
tion. United States v. Jones, 2019 U.S. Dist. LEXIS 101507 (W.D.N.Y. June 18, 2019).
It agreed that “the principle of collateral estoppel” precluded Jones from challeng-
ing the validity of the Tennessee Warrants. Id. at *5–7. In the alternative, the dis-
trict court held that suppression was unwarranted because the good-faith excep-
tion to the exclusionary rule applies. Id. at *7–8. Jones pleaded guilty to Count
Two of the indictment pursuant to a plea agreement but reserved the right to ap-
peal the denial of his motion to suppress.
DISCUSSION
Jones argues that the district court erred in concluding that (1) his prior
guilty plea in Tennessee state court collaterally estops him from challenging the
Tennessee Warrants and (2) the good-faith exception to the exclusionary rule pre-
cludes suppression. We agree with Jones that the district court erred in precluding
Jones from challenging the Tennessee Warrants but disagree that exclusion is re-
quired here.
9
I.
A.
We begin with collateral estoppel. “Issue preclusion, also referred to as col-
lateral estoppel, 3 bars ‘successive litigation of an issue of fact or law actually liti-
gated and resolved in a valid court determination essential to a prior judgment.’”
Cayuga Nation v. Tanner, 6 F.4th 361, 374 (2d Cir. 2021) (quoting New Hampshire v.
Maine, 532 U.S. 742, 748–49 (2001)); see also 18 Charles Alan Wright, Arthur R. Mil-
ler & Edward H. Cooper, Federal Practice & Procedure § 4416 (3d ed. Apr. 2022 up-
date); Restatement (Second) of Judgments § 27 (Am. L. Inst. 1982) (“Restate-
ment”). 4
“Although . . . developed in civil litigation,” the doctrine of issue preclusion
has been “extended” into the criminal sphere. Yeager, 557 U.S. at 119 n.4. More
than a century ago, the Supreme Court “recognized in federal criminal prosecu-
tions a claim of what was called res judicata, but which today would be described
as collateral estoppel” or issue preclusion. United States ex rel. DiGiangiemo v.
3The Supreme Court “has observed” that “‘issue preclusion’ is the more descrip-
tive term.” Bravo-Fernandez v. United States, 137 S. Ct. 352, 356 n.1 (2016) (quoting Yeager
v. United States, 557 U.S. 110, 120 n.4 (2009)).
4 Unless otherwise indicated, we omit all internal citations, quotation marks, alter-
ations, emphases, and footnotes from citations.
10
Regan, 528 F.2d 1262, 1264 (2d Cir. 1975) (Friendly, J.) (citing United States v. Op-
penheimer, 242 U.S. 85 (1916) (Holmes, J.)); see also Currier v. Virginia, 138 S. Ct. 2144,
2159 (2018) (Ginsburg, J., dissenting). And in Ashe v. Swenson, 397 U.S. 436 (1970),
the Supreme Court “link[ed] the issue-preclusion inquiry to the Double Jeopardy
Clause” of the Fifth Amendment. Bravo-Fernandez, 137 S. Ct. at 358 & n.2. Since
Ashe, we have recognized that there is an “‘issue preclusion’ component” of the
Double Jeopardy Clause, which “precludes the Government from relitigating any
issue that was necessarily decided by a jury’s acquittal in a prior trial.” United
States v. Hicks, 5 F.4th 270, 275 (2d Cir. 2021) (quoting Yeager, 557 U.S. at 119).
Although the Supreme Court “has not addressed directly the question of
whether collateral estoppel can be applied against the defendant in a criminal
case,” United States v. Gallardo-Mendez, 150 F.3d 1240, 1242 (10th Cir. 1998); see also
Currier, 138 S. Ct. at 2155 (plurality opinion), most courts have held that the Con-
stitution does not permit the government to preclude a defendant from contesting
an element of a criminal offense, see Gallardo-Mendez, 150 F.3d at 1246; United States
v. Smith Baltiher, 424 F.3d 913, 920–23 (9th Cir. 2005); United States v. Pelullo, 14 F.3d
881, 889–97 (3d Cir. 1994); United States v. Harnage, 976 F.2d 633, 634–36 (11th Cir.
11
1992); State v. Hewins, 760 S.E.2d 814, 822–23 (S.C. 2014) (collecting state court de-
cisions holding the same). 5
We agree with this consensus because the Fifth Amendment’s due process
guarantee and the Sixth Amendment’s jury trial guarantee “require criminal con-
victions to rest upon a jury determination that the defendant is guilty of every
element of the crime with which he is charged, beyond a reasonable doubt.”
United States v. Gaudin, 515 U.S. 506, 510 (1995); see also Sandstrom v. Montana, 442
U.S. 510, 523 (1979) (noting “the overriding presumption of innocence with which
the law endows the accused and which extends to every element of the crime”).
Precluding a criminal defendant from relitigating an element of a criminal of-
fense—in effect, issuing a partial directed verdict in the government’s favor on that
element—would impermissibly “invade the factfinding function which in a crim-
inal case the law assigns solely to the jury.” Sandstrom, 442 U.S. at 523; see also
United States v. Singleton, 532 F.2d 199, 206 (2d Cir. 1976) (noting that a partial
5 In at least two Ninth Circuit cases, the federal government agreed. See Smith Bal-
tiher, 424 F.3d at 920 (“[T]he government abandoned its defense of the use of offensive
collateral estoppel against criminal defendants, informing us that ‘in federal criminal tri-
als, the United States may not use collateral estoppel to establish, as a matter of law, an
element of an offense or to conclusively rebut an affirmative defense on which the Gov-
ernment bears the burden of proof beyond a reasonable doubt.’” (quoting United States v.
Arnett, 353 F.3d 765, 766 (9th Cir. 2003) (en banc))).
12
directed verdict in the government’s favor in a criminal case would be an “unjus-
tifiable encroachment upon the jury’s sole duty, i.e., to decide all issues of fact”). 6
The “constitutional concerns” that would arise from precluding a criminal
defendant from contesting an element of an offense, however, do not apply to sup-
pression motions. United States v. Shaw, 2017 U.S. Dist. LEXIS 58433, at *12
(S.D.N.Y. Apr. 13, 2017) (Sullivan, J.). Such motions are “adjudicated by judges,”
not juries, “and determined based on the preponderance of the evidence for the
limited purpose of admitting or excluding evidence at trial.” Id. (citing United
States v. Matlock, 415 U.S. 164, 173–74 (1974)). And “[a]lthough the doctrine of col-
lateral estoppel as to the facts determined at the trial of criminal cases does not run
both ways” because it applies only against the government, “this does not bar ap-
plication of a collateral estoppel rule [to suppression motions].” 6 Wayne R.
LaFave, Search and Seizure § 11.2(g) (6th ed. Dec. 2021 update).
We have previously suggested in dicta that a defendant may be precluded
from relitigating a motion to suppress. See Laaman v. United States, 973 F.2d 107,
6 This conclusion casts no doubt on our prior holding that “a criminal conviction,
whether by jury verdict or guilty plea, constitutes estoppel in favor of the United States
in a subsequent civil proceeding as to those matters determined by the judgment in the
criminal case.” Maietta v. Artuz, 84 F.3d 100, 102 n.1 (2d Cir. 1996) (emphasis added).
13
113 (2d Cir. 1992) (noting that “a prior decision by another court on a motion to
suppress is not ordinarily reconsidered in the absence of substantial new evidence
or extraordinary circumstances” and collecting authorities). Most courts have
agreed. See, e.g., United States v. McManaman, 673 F.3d 841, 847 (8th Cir. 2012);
Shaw, 2017 U.S. Dist. LEXIS 58433, at *12–14 (collecting cases); United States v.
Walker, 239 F. Supp. 3d 738, 740 (S.D.N.Y. 2017); Hewins, 760 S.E. at 823; see also
Anne Bowen Poulin, Prosecution Use of Estoppel and Related Doctrines in Criminal
Cases: Promoting Consistency, Tolerating Inconsistency, 64 Rutgers L. Rev. 409, 432–
33 & nn.98–99 (2012) (collecting cases).
Supreme Court teaching in a related context supports—and may even re-
quire—the same conclusion. The Court has held that when a court denies a motion
to suppress, the defendant may be precluded from relitigating the Fourth Amend-
ment issue in a subsequent civil action under 42 U.S.C. § 1983. Allen v. McCurry,
449 U.S. 90, 103–05 (1980); see also Owens v. Treder, 873 F.2d 604, 607 (2d Cir. 1989)
(“Principles of collateral estoppel may bar relitigation in a subsequent civil rights
action in federal court of an issue that was determined in a state court criminal
proceeding.”). Allen rejected the “principle that every person asserting a federal
right is entitled to one unencumbered opportunity to litigate that right in a federal
14
district court, regardless of the legal posture in which the federal claim arises,” and
the argument that constitutional rules may rest on “a general distrust of the capac-
ity of the state courts to render correct decisions on constitutional issues.” 449 U.S.
at 103, 105. Though Allen arose in the civil context, we see no persuasive reason to
distinguish between the preclusive effect of a previously litigated Fourth Amend-
ment claim in a subsequent § 1983 action and in a subsequent prosecution. We
therefore conclude that precluding a criminal defendant from relitigating a sup-
pression motion—so long as the defendant had a full and fair opportunity to liti-
gate the issue once—is not per se unconstitutional. 7
B.
Next, we consider whether, under Tennessee law, Jones’s guilty plea pre-
cludes him from challenging the Tennessee Warrants. Like any other state court
7 We note that, with only narrow exceptions, nonparties are not subject to issue
preclusion. Restatement § 27; see also Taylor v. Sturgell, 553 U.S. 880, 892–93 (2008) (“The
application of claim and issue preclusion to nonparties . . . runs up against the deep-
rooted historic tradition that everyone should have his own day in court.”). For that rea-
son, we do not disturb the longstanding “rule in this Circuit that collateral estoppel never
bars the United States from using evidence previously suppressed in a state proceeding
in which the United States was not a party.” United States v. Miller, 116 F.3d 641, 663 (2d
Cir. 1997); see also United States v. Peterson, 100 F.3d 7, 12 (2d Cir. 1996) (noting that “crim-
inal collateral estoppel . . . generally may not be invoked against one sovereign on the
basis of a ruling in a prosecution brought by a different sovereign”); United States v. Davis,
906 F.2d 829, 835 (2d Cir. 1990) (similar); 6 LaFave, supra, § 11.2(g) (similar).
15
judgment, “the preclusive effect of a guilty plea entered in state court upon subse-
quent federal proceedings is determined on the basis of collateral estoppel and the
full faith and credit statute.” Gregg, 463 F.3d at 165; see also Watley v. Dep’t of Child.
& Families, 991 F.3d 418, 425 (2d Cir. 2021). We must therefore determine whether
Tennessee courts would apply issue preclusion against Jones in the circumstances
presented here. We conclude they would not because the government has pro-
duced no evidence (and does not argue) that the suppression issue was actually
litigated or decided in the prior state case.
To begin, in State v. Flake, the Tennessee Supreme Court suggested that,
when the requirements for issue preclusion under Tennessee law are satisfied,
criminal defendants can be collaterally estopped from relitigating suppression mo-
tions. 114 S.W.3d 487, 507 (Tenn. 2003). Flake noted that “collateral estoppel likely
could be applied” to give preclusive effect to a prior suppression decision but pro-
ceeded to consider the merits of the defendant’s arguments as a matter of discre-
tion. Id. (emphasis added); see also State v. Mendenhall, 2020 Tenn. Crim. App.
LEXIS 343, at *76 (Crim. App. May 14, 2020). Relying on Flake, an intermediate
appellate court in Tennessee precluded a defendant from relitigating a motion to
suppress. See Mendenhall, 2020 Tenn. Crim. App. LEXIS 343, at *73–79 (noting that
16
suppression motions “are pretrial matters for the judge’s determination and do
not involve the jury or usurp [its] role as fact-finder”). But it appears that the Ten-
nessee Supreme Court has never squarely so held. See State v. Scarbrough, 181
S.W.3d 650, 655 n.3 (Tenn. 2005) (observing that Flake’s discussion of the issue was
dicta); Mendenhall, 2020 Tenn. Crim. App. LEXIS 343, at *76.
To the extent that this issue is unsettled under Tennessee law, we must
“carefully predict[] how the state’s highest court” would decide the issue. Tantaros
v. Fox News Network, LLC, 12 F.4th 135, 142 (2d Cir. 2021). “Our predictive inquiry
is guided by decisions of the state’s lower courts, decisions on the same issue in
other jurisdictions, and other sources the state’s highest court might rely upon in
deciding the question.” Id. We think it likely that the Tennessee Supreme Court
would permit the government to preclude criminal defendants from relitigating
suppression motions based on the Tennessee Supreme Court’s dictum in Flake, the
well-reasoned decision in Mendenhall, and the weight of authority in other juris-
dictions.
We need not resolve this issue, however. Even assuming arguendo that Ten-
nessee courts would apply issue preclusion to suppression motions in some cases,
the government has failed to meet its burden to show that the doctrine applies
17
here. Under Tennessee law, collateral estoppel “bars the same parties or their priv-
ies from relitigating in a later proceeding legal or factual issues that were actually
raised and necessarily determined in an earlier proceeding.” Mullins v. State, 294 S.W.3d
529, 534 (Tenn. 2009) (emphasis added); accord Mendenhall, 2020 Tenn. Crim. App.
LEXIS 343, at *74. In Tennessee,
[t]he party invoking collateral estoppel has the burden of
proof. To prevail with a collateral estoppel claim, the
party asserting it must demonstrate (1) that the issue to
be precluded is identical to an issue decided in an earlier
proceeding, (2) that the issue to be precluded was actu-
ally raised, litigated, and decided on the merits in the ear-
lier proceeding, (3) that the judgment in the earlier pro-
ceeding has become final, (4) that the party against
whom collateral estoppel is asserted was a party or is in
privity with a party to the earlier proceeding, and (5) that
the party against whom collateral estoppel is asserted
had a full and fair opportunity in the earlier proceeding
to contest the issue now sought to be precluded.
Moreover, in order for the doctrine of collateral estoppel
to apply, the issue must not only have been actually liti-
gated and decided, it must also have been necessary to
the judgment. Determinations of an issue or issues that
are not necessary to a judgment have the characteristics
of dicta and will not be given preclusive effect.
Mullins, 294 S.W.3d at 535; see also Bowen v. Arnold, 502 S.W.3d 102, 107 (Tenn.
2016); Mendenhall, 2020 Tenn. Crim. App. LEXIS 343, at *74.
18
Applying Tennessee’s test for issue preclusion, we conclude that the gov-
ernment has not established a basis for precluding Jones from challenging the Ten-
nessee Warrants. The government has not shown that a Fourth Amendment issue
in the present case “is identical to an issue decided in [the] earlier [state criminal]
proceeding,” nor even that any such issue “was actually raised,” much less “liti-
gated, and decided on the merits in the earlier proceeding.” Bowen, 502 S.W.3d at
107. To be sure, for an issue to have been “actually litigated” under Tennessee
law, it need not “have been litigated in a full evidentiary and adversarial trial.”
Mullins, 294 S.W.3d at 536. But the issue must have been “properly raised by the
pleadings or otherwise placed in issue” and “actually determined in the prior pro-
ceeding.” Id. And here, the government has not shown that Jones raised any
Fourth Amendment challenge to the Tennessee Warrants in the prior state case,
much less that resolution of this Fourth Amendment issue was “necessary to the
judgment.” Id.C.
The government does not argue that it has satisfied the requirements for
issue preclusion under Tennessee law. Instead, it relies on dicta in our decision in
Gregg to argue that Jones’s Fourth Amendment challenge is foreclosed because
19
“[t]he evidence recovered during the Tennessee state investigation is precisely the
same evidence that Jones seeks to suppress now in these federal court proceed-
ings.” Gov’t Br. 12. It is unclear whether the government intends to argue that
issue preclusion, waiver, or some other legal principle applies to bar Jones’s chal-
lenge. 8 In any event, for the reasons discussed below, we are not persuaded.
At the outset, our decision in Gregg relies heavily on the Supreme Court’s
decision in Haring v. Prosise, 462 U.S. 306 (1983). See Gregg, 463 F.3d at 164–66. And
Prosise fully supports our conclusion that Jones’s guilty plea in Tennessee does not
preclude his Fourth Amendment challenge here. In that case, Prosise pleaded
guilty to manufacturing a controlled substance after Virginia police officers found
incriminating evidence during a search of his apartment. Prosise, 462 U.S. at 308–
09. He subsequently sued the officers for violating his Fourth Amendments rights
under § 1983. The officers argued that Prosise’s guilty plea precluded him from
raising a Fourth Amendment claim in his civil case. Id. at 309–10.
8 The government argued before the magistrate judge that Jones “has waived and
abandoned his Fourth Amendment rights with respect to the specific evidence at issue.”
R&R, 2019 U.S. Dist. LEXIS 101810, at *5. The magistrate judge specifically rejected that
argument but held that Jones was “collaterally estopped” from challenging the Tennessee
Warrants under Gregg. Id. The district court similarly held that “under principles of col-
lateral estoppel, [Jones] is now barred” from challenging the Tennessee Warrants in this
case. Jones, 2019 U.S. Dist. LEXIS 101507, at *7.
20
After reviewing the requirements for issue preclusion under Virginia law—
which are the same as those under Tennessee law in all respects relevant here—
the Supreme Court rejected the officers’ argument. The Court noted that no Fourth
Amendment issue was litigated in the criminal proceeding or was “essential” to
Prosise’s guilty plea and that the criminal court did not actually decide against
Prosise on any issue on which he had to prevail to establish his § 1983 claim. Id. at
316. Observing that a defendant’s guilty plea may have any number of motiva-
tions, the Court similarly rejected the arguments that, by pleading guilty, Prosise
had admitted that the search of his apartment was lawful under the Fourth
Amendment or had waived any claim involving an antecedent Fourth Amend-
ment violation. Id. at 318–20; see also 18 Wright, Miller & Cooper, supra, § 4474.1
(noting that “a rational person” might “prefer the consequences of pleading guilty
to the costs and uncertainties of enduring through trial”).
Prosise’s analysis fits this case like a glove. Jones’s guilty plea does not sat-
isfy the requirements for issue preclusion under Tennessee law. Nor did Jones’s
plea “constitute[] an admission” that the Tennessee Warrants were proper or a
“waiver” of Jones’s Fourth Amendment claim in a subsequent case. Prosise, 462
U.S. at 318–20.
21
Gregg, which applied Prosise in the criminal context, supports this conclu-
sion. There, New York City police officers arrested Gregg, a felon, after he illegally
used his mother’s “disability fare Metrocard.” Gregg, 463 F.3d at 162. An arresting
officer searched Gregg incident to his arrest and discovered a firearm. Id. Gregg
pleaded guilty in New York state court to criminal impersonation in the second
degree and served a 15-day sentence. Id. A federal grand jury subsequently in-
dicted him on a felon-in-possession charge. Id. The district court concluded that
Gregg had waived any Fourth Amendment challenge in his federal firearms case
by pleading guilty to criminal impersonation in state court. But we rejected that
determination:
Just as the Court determined in Prosise that the defend-
ant’s guilty plea did not preclude him from seeking
§ 1983 damages for an alleged Fourth Amendment viola-
tion that was never considered in the state criminal pro-
ceedings, . . . Gregg should not have been barred—under
either waiver or collateral estoppel principles—from
challenging the seizure of the gun on Fourth Amend-
ment grounds. The legality of the firearm seizure was
not at issue when Gregg pleaded guilty to criminal im-
personation.
Id. at 165–66.
The government contends that this analysis from Gregg is inapplicable be-
cause Jones seeks in this federal case to suppress the very same evidence recovered
22
during the Tennessee state investigation, barring any challenge to the Tennessee
Warrants. In so arguing, the government relies on the following dicta from Gregg:
Were Gregg challenging law enforcement’s conduct
leading up to his surrender of his mother’s Metrocard,
i.e., the discovery of the evidence supporting the criminal
impersonation charge to which he pled guilty, then . . .
Gregg’s Fourth Amendment claims would be foreclosed.
This is because the plea conclusively establishes his fac-
tual guilt on the impersonation charge; how the support-
ing evidence was recovered is irrelevant. That is not the
case here. In the instant case, Gregg challenges law en-
forcement’s seizure of the firearm after the recovery of the
misused Metrocard. Therefore, the validity of Gregg’s
criminal impersonation conviction could not be affected
by the alleged Fourth Amendment violations he asserted
on the federal felon-in-possession charge.
Id. at 166. 9
We disagree with Gregg’s dictum that if Gregg had “challeng[ed] law en-
forcement’s conduct leading up to . . . the discovery of the evidence supporting the
criminal impersonation charge to which he pled guilty, then . . . Gregg’s Fourth
Amendment claims would be foreclosed.” 463 F.3d at 166. Gregg relied mainly on
the Supreme Court’s decision in Tollett v. Henderson, 411 U.S. 258 (1973), for this
Gregg’s discussion of this issue was dicta because it addresses law enforcement
9
conduct that occurred before the discovery of the weapon, and Gregg did not even chal-
lenge that conduct. Thus, the discussion was not necessary to Gregg’s holding. See Gregg,
463 F.3d at 166.
23
assertion, but that case is inapposite. In Tollett, the Supreme Court held that a
habeas petitioner who had pleaded guilty could not collaterally challenge his con-
viction on Fourth Amendment grounds. Id. at 266–68. Citing Tollett, Prosise ex-
plained that “a Fourth Amendment claim ordinarily may not be raised in a habeas
proceeding following a plea of guilty.” 462 U.S. at 321. “[W]hen a defendant is
convicted pursuant to his guilty plea rather than a trial, the validity of that convic-
tion cannot be affected by an alleged Fourth Amendment violation because the
conviction does not rest in any way on evidence that may have been improperly
seized.” Id. (emphasis added). This conclusion “does not rest on any notion of
waiver” or issue preclusion, however, “but . . . on the simple fact that the [Fourth
Amendment] claim is irrelevant to the constitutional validity of the conviction.”
Id.Gregg’s overall analysis reaffirms this principle. We there concluded that
“the validity of Gregg’s criminal impersonation conviction could not be affected by
the alleged Fourth Amendment violations” because he pleaded guilty to that of-
fense. Id. (emphasis added). The same is true for Jones. He could not have at-
tacked the Tennessee Warrants on habeas review of his Tennessee conviction because
his guilty plea conclusively established his guilt as to that offense.
24
But that principle does not foreclose Jones’s Fourth Amendment challenge
here because Jones is not challenging his Tennessee conviction. True, “[b]y plead-
ing guilty to the state offense, [Jones] made a factual admission in that case that he
committed the charged state offense, thereby waiving any Fourth Amendment
claim that the state illegally seized his gun as evidence in that state prosecution.”
United States v. Farmer, 770 F.3d 1363, 1367 (10th Cir. 2014) (citing Prosise, 462 U.S.
at 321–23). But Jones’s “guilty plea did not waive his right to challenge the validity
of the search underlying his state conviction in other contexts.” Id. at 1366–67 (citing
Prosise, 462 U.S. at 308, 319–22); see Hewins, 760 S.E.2d at 820 (“[T]he waiver that
results from the entry of a guilty plea is confined to the offense that is the subject
of the plea.”); see also 6 LaFave, supra, § 11.2(g) (“[I]f the state prosecution resulted
in a plea of guilty (meaning the validity of that conviction is unaffected by any
alleged Fourth Amendment violation), such a ‘counseled guilty plea will not
waive defendant’s right to collaterally challenge alleged Fourth Amendment vio-
lations’ in a subsequent federal prosecution arising out of the same event.” (quot-
ing Gregg, 463 F.3d at 166)). To the extent that the dicta in Gregg on which the
government relies suggests otherwise, we decline to adopt it here.
25
Indeed, the totality of Gregg’s reasoning only confirms that Jones is not pre-
cluded from challenging the Tennessee Warrants in this case. Gregg concluded
that the defendant there “should not have been barred—under either waiver or
collateral estoppel principles—from challenging the seizure of the gun on Fourth
Amendment grounds” because the issue “was never considered in the state crim-
inal proceedings.” 463 F.3d at 165–66. And the panel emphasized that it published
an opinion on the subject to reject the “broad ‘waiver’ proposition adopted by the
district court.” Id. at 163. On balance, Gregg strongly supports our conclusion that
Jones is not collaterally estopped from challenging the Tennessee Warrants.
II.
We next turn to address the merits of Jones’s motion to suppress. The dis-
trict court denied Jones’s motion because, even assuming that Jones was not pre-
cluded from challenging the Tennessee Warrants, the good-faith exception to the
exclusionary rule applies. Jones, 2019 U.S. Dist. LEXIS 101507, at *7–8. We agree.
A.
1.
The Fourth Amendment protects “[t]he right of the people to be secure in
their persons, houses, papers, and effects, against unreasonable searches and sei-
zures” and prohibits the issuance of warrants without “probable cause, supported
26
by Oath or affirmation, and particularly describing the place to be searched, and
the persons or things to be seized.” U.S. Const. amend. IV. “The basic purpose of
this Amendment . . . is to safeguard the privacy and security of individuals against
arbitrary invasions by governmental officials.” Carpenter v. United States, 138 S. Ct.
2206, 2213 (2018). The Amendment’s “text makes clear” that “the ultimate touch-
stone of the Fourth Amendment is ‘reasonableness.’” Lange v. California, 141 S. Ct.
2011, 2017 (2021).
When the police undertake a search “to discover evidence of criminal
wrongdoing, reasonableness generally requires the obtaining of a judicial war-
rant.” Riley v. California, 573 U.S. 373, 382 (2014). Warrants “ensure[] that the in-
ferences to support a search are drawn by a neutral and detached magistrate in-
stead of being judged by the officer engaged in the often competitive enterprise of
ferreting out crime.” Id. Because warrants must be “supported by probable
cause,” Carpenter, 138 S. Ct. at 2213, warrants not so supported are “invalid,”
United States v. Raymonda, 780 F.3d 105, 113 (2d Cir. 2015).
“Probable cause ‘is not a high bar.’” District of Columbia v. Wesby, 138 S. Ct.
577, 586 (2018) (quoting Kaley v. United States, 571 U.S. 320, 338 (2014)). To deter-
mine whether probable cause to search exists, an issuing magistrate must “make
27
a practical, common-sense decision whether, given all the circumstances set forth
in [an] affidavit . . . , there is a fair probability that contraband or evidence of a
crime will be found in a particular place.” Illinois v. Gates, 462 U.S. 213, 238 (1983);
accord United States v. Boles, 914 F.3d 95, 102 (2d Cir. 2019). “Because probable
cause ‘deals with probabilities and depends on the totality of the circumstances,’
it is a ‘fluid concept’ that is ‘not readily, or even usefully, reduced to a neat set of
legal rules.’” Wesby, 138 S. Ct. at 586 (first quoting Maryland v. Pringle, 540 U.S.
366, 371 (2003), then quoting Gates, 462 U.S. at 232). Probable cause is a “practical,”
“common-sensical,” and “all-things-considered” standard. Florida v. Harris, 568
U.S. 237, 244 (2013); see also Wesby, 138 S. Ct. at 587 (holding that probable cause
permits law enforcement to draw “common-sense conclusions about human be-
havior” (quoting Gates, 562 U.S. at 231)). It “requires only the ‘kind of fair proba-
bility’ on which ‘reasonable and prudent people, not legal technicians, act.’” Kaley,
571 U.S. at 338 (quoting Harris, 568 U.S. at 244).
“On appeal from a district court’s ruling on a suppression motion, we re-
view a district court’s findings of fact for clear error, and its resolution of questions
of law and mixed questions of law and fact de novo.” United States v. Eldred, 933
F.3d 110, 114 (2d Cir. 2019). But in the context of a warrant-based search, “[w]e
28
accord substantial deference to the finding of an issuing judicial officer that prob-
able cause exists, limiting our inquiry to whether the officer had a substantial basis
for his determination.” Boles, 914 F.3d at 102; see also McLane Co. v. EEOC, 137 S.
Ct. 1159, 1169 (2017) (“[C]ourts should pay ‘great deference’ to a magistrate judge’s
determination of probable cause.” (quoting Gates, 462 U.S. at 236)). “This degree
of deference derives from a concern that ‘a grudging or negative attitude by re-
viewing courts toward warrants will tend to discourage police officers from sub-
mitting their evidence to a judicial officer before acting.’” United States v. Thomas,
788 F.3d 345, 350 (2d Cir. 2015) (quoting United States v. Ventresca, 380 U.S. 102, 108
(1965)).
2.
On appeal, Jones argues that the Tennessee Warrants were not supported
by probable cause. We are dubious. As set forth in Detective Brooks’s affidavits,
the Complainant reported that Jones plied her daughter and her daughter’s
friend—both underage and both of whom she identified by name—with alcohol
and drugs, took nude photographs of them, and made sexual advances toward
them. This statement at least arguably establishes “a fair probability that . . . evi-
dence of a crime” would be found on Jones’s devices. Gates, 462 U.S. at 238.
29
Jones objects that Detective Brooks’s affidavits do not provide adequate cor-
roboration for these allegations. But State Victim 1’s mother “was a person known
to law enforcement officers and not an anonymous tipster, a circumstance that we
have recognized weighs in favor of reliability.” McColley v. County of Rensselaer,
740 F.3d 817, 842 (2d Cir. 2014) (Raggi, J., dissenting) (citing United States v. Elmore,
482 F.3d 172, 180–81 (2d Cir. 2007) (explaining that information from a known in-
formant is entitled to greater weight because, among other things, a known in-
formant “runs a greater risk that he will be held accountable if his information
proves false”); United States v. Gagnon, 373 F.3d 230, 236 (2d Cir. 2004) (similar));
see also United States v. Salazar, 945 F.2d 47, 50–51 (2d Cir. 1991) (similar).
Jones also objects that the Tennessee Warrants do not spell out the basis for
the Complainant’s knowledge. But that objection gives short shrift to the “com-
mon-sensical” nature of the probable cause inquiry. Harris, 568 U.S. at 244. We
think it was at least arguably reasonable for the issuing magistrate to draw the
common-sense inference that State Victim 1’s mother spoke with her daughter about
Jones’s behavior. Though a “legal technician” could still object (as Jones does) that
this proposition is not made explicit in the warrant application, we believe a “rea-
sonable and prudent” person might well conclude that the Complainant’s
30
statements nevertheless clear the low threshold for probable cause, see Kaley, 571
U.S. at 338—or, more to the point, that the issuing magistrate had a substantial
basis for so concluding. See Gates, 462 U.S. at 236 (noting “great deference” owed
to the issuing judge’s probable cause assessment).
At any rate, we need not resolve the probable cause issue. This is because,
as set forth below, we agree with the district court that the good-faith exception to
the exclusionary rule applies.
B.
1.
“Even where a warrant was issued without probable cause in violation of
the Fourth Amendment, suppression of the evidence is not automatic.” Boles, 914
F.3d at 103. The exclusionary rule is a “judicially created” doctrine, Herring v.
United States, 555 U.S. 135, 139 (2009), that is “prudential” rather than constitution-
ally mandated, Davis v. United States, 564 U.S. 229, 236 (2011); accord Collins v. Vir-
ginia, 138 S. Ct. 1663, 1678 (2018) (Thomas, J., concurring) (quoting Penn. Bd. of Prob.
& Parole v. Scott, 524 U.S. 357, 363 (1998)). It therefore applies “only where its de-
terrence benefits outweigh its substantial social costs.” Utah v. Strieff, 579 U.S. 232,
237 (2016) (quoting Hudson v. Michigan, 547 U.S. 586, 591 (2006)); see also United
States v. Hightower, 950 F.3d 33, 36 (2d Cir. 2020) (“Because the rule is prudential
31
rather than constitutionally mandated, it is applicable only where its deterrence
benefits outweigh its substantial social costs.” (quoting Scott, 524 U.S. at 363)).
“The extent to which the exclusionary rule is justified by deterrence principles var-
ies with the culpability of the law enforcement conduct.” Herring, 555 U.S. at 143;
accord Eldred, 933 F.3d at 119. The exclusionary rule seeks to deter “intentional
conduct that [is] patently unconstitutional.’” Herring, 555 U.S. at 143; accord Lange,
141 S. Ct. at 2027 (Thomas, J., concurring). Because the exclusionary rule “exacts
a heavy toll” on the justice system, Davis, 564 U.S. at 237, it applies only to deter
law enforcement’s “deliberate, reckless, or grossly negligent conduct,” Herring,
555 U.S. at 144; accord Boles, 914 F.3d at 103. “[P]olice conduct must be sufficiently
deliberate that exclusion can meaningfully deter it, and sufficiently culpable that
such deterrence is worth the price paid by the justice system.” Herring, 555 U.S. at
144; accord In re 650 Fifth Ave., 934 F.3d 147, 162 (2d Cir. 2019).
In accord with these principles, the “good-faith exception” to the exclusion-
ary rule applies when the agents executing a search warrant “act with an objec-
tively reasonable good-faith belief that their conduct is lawful.” Davis, 564 U.S. at
238; accord Eldred, 933 F.3d at 118. It applies when the government acts in “objec-
tively reasonable reliance on a subsequently invalidated search warrant.” United
32
States v. Leon, 468 U.S. 897, 922 (1984); accord In re 650 Fifth Ave., 934 F.3d at 162.
“[W]hen an officer acting with objective good faith has obtained a search warrant
from a judge or magistrate and acted within its scope, . . . there is [generally] no
police illegality and thus nothing to deter.” Leon, 468 U.S. at 920–21; accord Purcell,
967 F.3d at 179; Boles, 914 F.3d at 103. The exclusionary rule has minimal deterrent
benefit in such cases because “the error rests with the issuing magistrate, not the
police officer.” Davis, 564 U.S. at 239; accord In re 650 Fifth Ave., 934 F.3d at 162.
And “[p]enalizing the officer for the magistrate’s error, rather than his own, cannot
logically contribute to the deterrence of Fourth Amendment violations.” Leon, 468
U.S. at 921; accord Purcell, 967 F.3d at 179; see also Davis, 564 U.S. at 239 (“[P]unish-
ing the errors of judges is not the office of the exclusionary rule.” (quoting Leon,
468 U.S. at 916)).
“For an officer to be able to claim the benefits of the good faith exception,
however, his reliance on a warrant must be objectively reasonable.” Boles, 914 F.3d
at 103 (citing Leon, 468 U.S. at 922).
[T]he Supreme Court in Leon delineated several situa-
tions in which the good-faith exception does not apply:
(1) the magistrate or judge “was misled by information
in an affidavit that the affiant knew was false or would
33
have known was false except for his reckless disregard of
the truth”;
(2) “where the issuing magistrate wholly abandoned his
judicial role”;
(3) a warrant was based on an affidavit “so lacking in in-
dicia of probable cause as to render official belief in its
existence entirely unreasonable”; and
(4) a warrant is so “facially deficient” that officers “can-
not reasonably presume it to be valid.”
Eldred, 933 F.3d at 118 (quoting Leon, 468 U.S. at 923); see also Boles, 914 F.3d at 103.
“[W]e review a district court’s determination to apply the good-faith exception
based on an officer’s reliance on an issued warrant de novo.” Eldred, 933 F.3d at
114.
2.
The district court correctly applied the good-faith exception in this case. As
we have already explained, there was at least arguable probable cause for the Ten-
nessee Warrants. We therefore conclude that Detective Brooks acted based on an
“‘objectively reasonable good-faith belief’ that [his] conduct [was] lawful.” Id. at
118 (quoting Davis, 564 U.S. at 238). Jones argues that the good-faith exception
does not apply here based on the third category enumerated above—that the Ten-
nessee “warrant[s] [were] based on an affidavit ‘so lacking in indicia of probable
34
cause as to render official belief in its existence entirely unreasonable.’” Id. (quot-
ing Leon, 468 U.S. at 923). We disagree.
This issue “most frequently arises when affidavits are bare bones”—that is,
when they are “totally devoid of factual circumstances to support conclusory alle-
gations.” United States v. Clark, 638 F.3d 89, 103 (2d Cir. 2011). We have empha-
sized that this is “a very difficult threshold to meet.” United States v. Falso, 544 F.3d
110, 128 n.24 (2d Cir. 2008) (Sotomayor, J.). The affidavits at issue here are not so
devoid of factual support because they detail allegations from State Victim 1’s
mother that support the common-sense inference that her daughter told her that
Jones took nude photographs of her.
Nor would the benefits of applying the exclusionary rule here “outweigh its
substantial social costs.” Strieff, 579 U.S. at 237. Before Detective Brooks sought
the Tennessee Warrants, he received signed statements from both victims corrob-
orating the Complainant’s allegations. Detective Brooks could have used those
statements to strengthen a renewed warrant application if Judge Dugger had de-
manded additional corroboration. For that reason, exclusion here would amount
to “penalizing the officer for the magistrate’s error,” Purcell, 967 F.3d at 179
35
(quoting Leon, 468 U.S. at 921), which is “not the office of the exclusionary rule,”
In re 650 Fifth Ave., 934 F.3d at 162 (quoting Davis, 564 U.S. at 239).
For similar reasons, Detective Brooks’s behavior was not the sort of “‘delib-
erate, reckless, or grossly negligent conduct’” that justifies the exclusionary rule’s
“heavy toll on the justice system.” Boles, 914 F.3d at 103 (quoting Herring, 555 U.S.
at 144). His conduct was neither “sufficiently deliberate that exclusion can mean-
ingfully deter it” nor “sufficiently culpable that such deterrence is worth the price
paid by the justice system.” In re 650 Fifth Ave., 934 F.3d at 162 (quoting Herring,
555 U.S. at 144). In this case, “exclusion cannot pay its way.” Eldred, 933 F.3d at
118 (quoting Davis, 564 U.S. at 238).
CONCLUSION
We have considered Jones’s remaining arguments and conclude that they
lack merit. We therefore AFFIRM the judgment of the district court.
36