                               In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 18-2778
UNITED STATES OF AMERICA,
                                                   Plaintiff-Appellee,
                                 v.

JIMMY L. DESOTELL,
                                               Defendant-Appellant.
                     ____________________

         Appeal from the United States District Court for the
                   Eastern District of Wisconsin.
         No. 17-CR-111 — William C. Griesbach, Chief Judge.
                     ____________________

       ARGUED APRIL 9, 2019 — DECIDED JULY 11, 2019
                ____________________

   Before KANNE, BARRETT, and BRENNAN, Circuit Judges.
    KANNE, Circuit Judge. Jimmy Desotell had an unexpected
encounter with police oﬃcers one evening in Green Bay, Wis-
consin. While he was trying to borrow a car from a friend, po-
lice arrived and informed him that the vehicle was suspected
of use in a retail theft. But after being told that he was not a
suspect and was free to leave, Desotell stuck around. He tried
to remove bags from the car as police were about to search it,
arousing the oﬃcers’ suspicion. As it turned out, the bags
2                                                  No. 18-2778

contained a ﬁrearm and drugs. After unsuccessfully trying to
suppress the evidence, he agreed to plead. Despite tensions
during negotiations, Desotell eventually signed a plea deal
expressly waiving his right to appeal the motion to suppress.
After an extensive colloquy in the district court hammering
home the waiver, Desotell now appeals the precise issue he
may not appeal. We therefore dismiss it as waived.
                       I. BACKGROUND
    Green Bay police arrested Desotell on May 30, 2017 while
investigating a retail theft. He admitted to owning two bags
containing methamphetamine and a handgun, which police
discovered while searching a vehicle that had been involved
in the theft earlier that day. Desotell was not a suspect in the
theft; he just happened to be in the wrong place, at the wrong
time, with the wrong stuﬀ.
    A grand jury indicted Desotell on two counts: 1) conspir-
acy to distribute, and to possess with intent to distribute, 500
grams or more of methamphetamine, 21 U.S.C. §§ 846,
841(b)(1)(A); and 2) knowingly using or carrying a ﬁrearm
during and in relation to a drug traﬃcking crime, 18 U.S.C.
§ 924(c)(1)(A). The district court appointed a Federal De-
fender to represent Desotell immediately after his arrest. Des-
otell agreed to plead guilty and cooperate with investigators,
giving useful information about his drug contacts. In return,
the government agreed not to ﬁle a prosecutor’s information
detailing Desotell’s prior convictions, thereby avoiding a
higher mandatory-minimum sentence.
    In December 2017, Desotell retained private attorney John
Miller Carroll and discharged his Federal Defender. Shortly
after obtaining new counsel, Desotell moved to suppress the
No. 18-2778                                                 3

evidence found in his bags, arguing that his detention at the
scene and the search violated the Fourth Amendment.
    While the motion was pending, the government informed
Desotell that he had to sign the plea agreement by March 9,
2018. Presumably, signing the agreement would have meant
withdrawing the motion to suppress, so Desotell delayed. The
deadline came and went without a ruling on the motion, and
Desotell did not sign the agreement. The government, assum-
ing that Desotell intended to litigate his motion rather than
plead guilty, acted as if the agreement were no longer on the
table. It ﬁled the information and continued to prepare for
trial. Desotell objected and moved to enforce the unsigned
plea agreement. The court denied the motion to suppress on
April 19. Desotell then came back to the table. He signed a
plea agreement and the government withdrew the infor-
mation.
    The district court held a change-of-plea hearing on May 8.
The court ﬁrst conﬁrmed the parties’ understanding that the
agreement was a general plea, not a conditional plea. In other
words, the document contained “no reservations of any right
to appeal from the denial of the Motion to Suppress.” Deso-
tell, through his counsel (Carroll), agreed that the document
“contain[ed] a general clause about waiving any pretrial mo-
tions.” But then defense counsel emphasized that he did not
believe the waiver was eﬀective because, at the time Desotell
initially agreed to the wording, he had not contemplated ﬁl-
ing his motion to suppress. In counsel’s view, the general
waiver did not bar an appeal of that motion.
   The district court expressed its confusion with this argu-
ment. It iterated several times that, in the federal system, a
defendant must expressly reserve his right to appeal in the
4                                                     No. 18-2778

text of the plea agreement. Counsel acknowledged the court’s
admonishment, but he refused to accept it:
      MR. CARROLL: Right. I fully understand that, Your
      Honor, and I think that it’s — It’s just that I don’t
      think it’s correct, and it should be — The Government
      shouldn’t be — control the ability of a defendant to
      appeal in a criminal case.
      …
      THE COURT: You may be — Maybe, you’re right.
      You can disagree with the way the law is. But if
      you’re advising your client that he has the right to
      appeal the denial of his Motion to Suppress, there’s a
      problem. Your client is entering a plea with a false
      understanding of the law, and you’re supposed to tell
      him what the law is.
      …
      MR. CARROLL: No, I have not said that. I said, he’s
      not appealing. We had a discussion on Sunday about
      that, and he understands that. I’m just — I’m trying
      to make it clear on the record what’s actually happen-
      ing here is the Government is controlling how this
      man is going to proceed, and he’s basically being de-
      nied the right to appeal. In exchange, they’re going to
      give him a 25 year sentence versus a 15. [sic] … [W]e
      made it very clear that we were accepting the plea
      agreement, and we wanted to reserve our appeal
      rights. And they basically just said that we have to
      accept this as written, and this, as written preceded
      that motion. So I’m just trying to put in the record
      that that motion is out there, and that he understands
      they’re not agreeing to allow him to appeal.
No. 18-2778                                                    5

      THE COURT: Okay. All right. And you intend to re-
      ally challenge that law, the Government’s argument
      that he’s not free to appeal.
      MR. CARROLL: Correct.
      THE COURT: Okay. I don’t know if that’s tilting at
      windmills or not. That’s ﬁne as long as your client
      understands the law, as it stands now, is that unless
      there’s a reservation, a speciﬁc reservation that the
      Government agrees to allowing him to appeal the de-
      nial of his Motion to Suppress, entering the plea
      waives that right.
      MR. CARROLL: No, right. … We understand that.
The court summarized the stakes for Desotell and outlined his
options in the wake of the denial of the motion to suppress:
      Of course, you know, the Government also has the
      ability to ﬁle the Information as they did and seek a
      25 year sentence instead of a 15. That’s the quid pro
      quo that’s being oﬀered here, and I agree. It’s a diﬃ-
      cult decision to make. … Do I want to risk a 25 year
      sentence in order to appeal, or do I simply want to
      take the 15… ?
   The hearing proceeded as usual. After Desotell himself
acknowledged the charges against him and provided a factual
basis for his plea, the court advised him of the rights he was
waiving by agreeing to plead guilty. The court again broached
the matter of an appeal:
      THE COURT: Now, the other thing that I want you
      to understand is that under the law, as it now stands,
      and your attorney may disagree with this law, but
      my understanding of the law and what I want you
      to understand is that there’s no right to appeal any
6                                                       No. 18-2778

       pretrial ruling once you enter a plea of guilty, unless
       that’s expressly preserved in the plea agreement.
       And the Government has not entered into an agree-
       ment where that’s expressly preserved.
       So your attorney may have an argument that he
       thinks he can win on, but my understanding of the
       law and you should understand this — is this, unless
       your attorney can succeed in changing the law,
       you’re giving up your right to appeal from my deci-
       sion denying your Motion to Suppress. Do you un-
       derstand that?
       DEFENDANT: Yes, your honor.
The court accepted the plea and later sentenced Desotell to
180 months in prison—the mandatory minimum sentence on
his drug and ﬁrearms charges.
    Desotell appealed. Mr. Carroll continued his representa-
tion by our appointment. But curiously, the docketing state-
ment omitted any mention of the appeal waiver. It stated an
intention to challenge the denial of the motion to suppress,
but there was no indication of an intent to challenge the plea
agreement or the law of waiver generally. Likewise, Desotell’s
opening brief skipped straight to the merits question; there
was no mention of any waiver. The government raised the is-
sue in its response, and Desotell addressed it in his reply brief,
where he asserted that the government coerced him into
waiving his appellate rights by threatening to pursue an in-
creased mandatory sentence if Desotell proceeded to trial.
                           II. ANALYSIS
    Desotell asks us to review the denial of his motion to sup-
press. He argues that the oﬃcers did not have reasonable sus-
picion to detain him or probable cause to search his bags. But
No. 18-2778                                                    7

we cannot reach the merits of the Fourth Amendment argu-
ment because Desotell waived it—twice.
    At the change-of-plea hearing, counsel informed the dis-
trict court that Desotell intended to appeal the validity of the
appeal waiver contained in the plea agreement. The court pre-
dicted that it would be a losing argument, but it agreed that
Desotell was within his rights to raise it in the court of ap-
peals. Inconceivably, Desotell’s brief omitted the argument
completely. Even after the government raised the waiver as a
bar to relief in its response brief (and noted Desotell’s failure
to mention it), Desotell pretended as if the omission were ir-
relevant and made a lengthy argument about why the waiver
is invalid.
   When we pressed defense counsel for an explanation at
oral argument, his excuse was unsatisfactory: he wanted us to
“focus on the search issue.” That may be true, but it seems
more likely that he wanted to hide the ball from us and hope
that neither we nor the government would realize that his cli-
ent waived his right to appeal.
    Counsel was present at the change-of-plea hearing and
participated in the extensive colloquy with the district court.
The court made it exceptionally clear that the waiver barred
an appeal and that Desotell would need to challenge the va-
lidity of the waiver successfully before appealing the Fourth
Amendment issue. That might be enough to resolve this ap-
peal. In most instances, litigants waive any arguments they
make for the ﬁrst time in a reply brief. Carroll v. Lynch, 698
F.3d 561, 568 (7th Cir. 2012); Gonzalez-Servin v. Ford Motor Co.,
662 F.3d 931, 934 (7th Cir. 2011).
8                                                     No. 18-2778

     But we acknowledge that there is an existing circuit split
on the narrower question of whether a criminal defendant
must raise the issue of an appeal waiver in his opening brief
or whether it falls upon the government to raise the waiver as
a defense in its reply. See United States v. Goodson, 544 F.3d 529,
533–36 (3d Cir. 2008) (“[A] defendant is not obliged in his
opening brief to acknowledge the existence of an appellate
waiver and/or to explain why the waiver does not preclude
appellate review of the substantive issue. Rather, it is only af-
ter the government has invoked an appellate waiver as a bar
to our review that a defendant must raise any challenge to the
waiver’s enforceability.”); United States v. Powers, 885 F.3d 728,
732 (D.C. Cir. 2018) (same); but see United States v. Arroyo-Blas,
783 F.3d 361, 366 (1st Cir. 2015) (“We expect and require coun-
sel to address a waiver of appeal head-on and explain why we
should entertain the appeal.”).
    The parties in this case have not asked us to take a position
in that split. Moreover, because we proceed below to evaluate
the validity of Desotell’s appeal waiver “in an abundance of
caution” and ﬁnd that he waived this appeal on alternative
grounds, we need not take a position on whether his failure
to include the issue in his opening brief constitutes waiver.
Arroyo-Blas, 783 F.3d at 367 (quoting United States v. Gil-Que-
zada, 445 F.3d 33, 37 (1st Cir. 2006) (modiﬁcation deleted)). We
only note that the evidence of waiver is exceptionally strong
in this case. The district court’s repeated insistence of the ef-
fectiveness of the appeal waiver made it clear that Desotell’s
only hope for an appeal was one challenging the waiver’s va-
lidity itself. Counsel’s failure to bring that issue to our atten-
tion up front is disappointing.
No. 18-2778                                                        9

    But Desotell deserves a better explanation than simply
that his lawyer failed to make an argument in the opening
brief. He should understand why the waiver bars him from
appealing his motion to suppress. “[A] defendant may waive
the right to appeal his conviction and sentence.” United States
v. Cole, 569 F.3d 774, 776 (7th Cir. 2009) (citing Fed. R. Crim.
P. 11(b)(1)(N)). “Generally speaking, appeal waivers are en-
forceable and preclude appellate review.” United States v.
Worthen, 842 F.3d 552, 554 (7th Cir. 2016). We interpret them
according to principles of contract law. United States v. Wil-
liams, 184 F.3d 666, 668 (7th Cir. 1999).
    “To determine whether the plea was knowing and volun-
tary, we ask ‘whether, looking at the total circumstances sur-
rounding the plea, the defendant was informed of his …
rights.’” United States v. Perillo, 897 F.3d 878, 883 (7th Cir. 2018)
(quoting United States v. Kelly, 337 F.3d 897, 902 (7th Cir.
2003)). A knowing and voluntary waiver “must be enforced.”
Id. at 882 (quoting United States v. Sakellarion, 649 F.3d 634, 638
(7th Cir. 2011)).
    Under Fed. R. Crim. P 11(a)(2), a defendant must
“reserv[e] in writing the right to have an appellate court re-
view an adverse determination of a speciﬁed pretrial motion.”
Interpreting that rule, we’ve held that “[t]o preserve an issue
for appeal, a conditional plea must precisely identify which
pretrial issues the defendant wishes to preserve for review.”
United States v. Kingcade, 562 F.3d 794, 797 (7th Cir. 2009) (in-
ternal quotation omitted)). “All non-jurisdictional issues not
speciﬁcally preserved in the conditional plea agreement are
waived.” Id. (citations omitted).
   Desotell’s signed plea agreement is clear: “the defendant
acknowledges and understands that he surrenders any claims
10                                                  No. 18-2778

he may have raised in any pretrial motion.” Desotell argues
that there were two versions of the plea agreement: the ﬁrst
(March), to which he agreed but failed to sign before the gov-
ernment’s deadline, and the second (May), which he signed
and which was the basis for his conviction. See Br. for App. at
5. He contends that the ﬁrst version did not contain the appeal
waiver and that the government coerced him into signing the
new version by threatening to seek a higher sentence if he
went to trial. Id. But both versions appear to be the same doc-
ument and contain the exact same waiver language. (Compare
R. 184-6 at ¶ 27 with R. 195 at ¶ 27.) In fact, it appears that
Desotell’s signature and date on both documents is identical,
suggesting that there was never a second edition.
    Any argument that the district court should have enforced
the “ﬁrst” version rather than the “second” version has no
bearing on whether Desotell waived his right to appeal. Alt-
hough Desotell tried to bargain for removal of the waiver lan-
guage early in negotiations (see R. 184-1), the government
never agreed. “[T]he parties’ rights under the plea agreement
are limited to those matters upon which they actually
agreed.” United States v. Williams, 102 F.3d 923, 927 (7th Cir.
1996) (citation omitted). This waiver is consistent with the law
of pleas: “[a] valid guilty plea … renders irrelevant—and
thereby prevents the defendant from appealing—the consti-
tutionality of case-related government conduct that takes
place before the plea is entered.” United States v. Class, 138 S.
Ct. 798, 805 (2018) (citing Haring v. Prosise, 462 U.S. 306, 321
(1983) (a valid guilty plea “results in the defendant’s loss of
any meaningful opportunity he might otherwise have had to
challenge the admissibility of evidence obtained in violation
of the Fourth Amendment.”)).
No. 18-2778                                                      11

    Once a defendant pleads guilty, the government has no
need to rely on evidence (that it may have obtained impermis-
sibly) to secure a conviction. There is no question that Desotell
was aware of this fact when he entered his plea. The district
court went to great lengths to ensure that he understood what
rights he was surrendering in return for a lighter sentence
than he otherwise might have received after trial.
                        III. CONCLUSION
    Desotell faced a stark choice: accept the agreement (with
the waiver) for a 15-year sentence, or reject the deal, go to trial,
and risk 25 years with enhancements for prior convictions.
But over counsel’s protestations regarding the morality of
pleas, the district court correctly instructed Desotell on the
law of waiver. Desotell chose to plead guilty.
    Moreover, his attorney failed to make any good-faith ar-
gument about the validity of the waiver or the constitutional-
ity of plea bargaining. Faced with a rare double waiver, we
cannot reach the merits of the Fourth Amendment claim. The
appeal is DISMISSED.
