Court Opinion

ID: 9365576
Source: CourtListenerOpinion
Date Created: 2023-01-24 17:00:36.338809+00
Date Added: 2024-06-11T17:15:46.265727
License: Public Domain

United States Court of Appeals
                           For the Eighth Circuit
                       ___________________________

                               No. 21-3690
                       ___________________________

                           United States of America

                                     Plaintiff - Appellee

                                       v.

                            Marlin Santana Thomas

                                  Defendant - Appellant
                                ____________

                    Appeal from United States District Court
                   for the Southern District of Iowa - Central
                                ____________

                        Submitted: September 27, 2022
                           Filed: January 24, 2023
                               ____________

Before GRUENDER, SHEPHERD, and ERICKSON, Circuit Judges.
                        ____________

GRUENDER, Circuit Judge.

      Marlin Thomas appeals his 2021 conviction for various sex-trafficking
offenses. He argues that the Government was prohibited from prosecuting him
based on a “No Further Prosecution” clause in a prior 2018 plea agreement that
resolved heroin-related charges against him. We conclude that the prior plea
agreement’s promise of no further prosecution encompasses the sex-trafficking
convictions appealed here. We therefore reverse the denial of Thomas’s motion to
dismiss the indictment and vacate his conviction.

                                          I.

      In May 2018, Thomas pleaded guilty in the Southern District of Iowa to one
count of conspiracy to distribute heroin in violation of 21 U.S.C. §§ 841(a)(1) and
846. In exchange, the Government agreed to dismiss the other four counts of the
indictment. The plea agreement also contained a “No Further Prosecution” clause,
which stated:

      The Government agrees that Defendant will not be charged in the
      Southern District of Iowa with any other federal criminal offense
      arising from or directly relating to this investigation. This paragraph
      and this Plea Agreement do not apply to (1) any criminal act occurring
      after the date of this agreement, (2) any crime of violence, or (3) any
      criminal offense which Defendant did not fully disclose to law
      enforcement during Defendant’s interviews pursuant to any proffer or
      other agreements with the United States.

       Thomas’s appeal concerns the scope of this clause, and interpreting it requires
background on that earlier case. More specifically, his appeal hinges on whether
“any other federal criminal offense arising from or directly relating to this
investigation” encompasses the sex-trafficking charges that led to his present
conviction.1

      1
        Before the district court, the Government argued that the sex-trafficking
charges were “crimes of violence” within the plea agreement’s exception. The
district court disagreed and declined to deny dismissal on that ground. The
Government did not appeal that ruling. Nor does the Government argue on appeal
that any of the exceptions apply to permit prosecution of the sex-trafficking offenses.
Indeed, the Government conceded at oral argument that the clause’s three exceptions
are not at issue. We therefore deem any argument that the three exceptions might
apply to the sex-trafficking charges waived. See United States v. Greene, 513 F.3d
904, 906-07 (8th Cir. 2008) (finding that the government had waived an argument

                                         -2-
       The federal investigation into Thomas began in early 2018. 2 It was carried
out with the assistance of the Des Moines Police Department (“DMPD”) following
a tip that Thomas was dealing heroin. The principal federal prosecutors were
Assistant United States Attorneys (“AUSA”) Amy Jennings and Virginia Bruner.
At the time, Thomas faced Iowa state charges for human trafficking of a minor, G.M.
DMPD interviews with G.M. prior to the federal investigation revealed that Thomas
provided drugs to her, had sex with her, and sexually trafficked her using
advertisements on Backpage.com, an escort-services website, to arrange hotel
meetups with men. By early February 2018, the U.S. Attorney’s Office learned of
the pending state charges. On February 9, AUSA Bruner served a subpoena on
Backpage.com for records related to Thomas based on details learned from the
pending G.M. case.

       The AUSAs and DMPD officers continued to investigate Thomas’s heroin
activity. In February, they orchestrated three controlled buys from him. On
February 28, DMPD officers, including Todd Wilshusen and Brady Carney,
executed a federal search warrant for Thomas’s apartment and car. They seized

premised on the plea agreement because it failed to raise the argument in its opening
brief).
      2
        These facts come from the parties’ briefing and exhibits before the district
court on Thomas’s motion to dismiss the indictment. In addition, Thomas filed a
motion arguing that this Court should consider certain transcriptions that his
attorneys made from Des Moines Police Department (“DMPD”) officer interviews
with alleged victims in the sex-trafficking case. The Government had provided
audio of these interviews to Thomas during discovery but not the physical recordings
themselves, and the interviews were never made part of the record. Thomas included
these transcriptions in his briefing before the district court and here in his opening
brief. In the alternative, Thomas moved to supplement the record on appeal with the
actual interviews. The Government does not object to us considering the limited
transcriptions that appear in briefing but objects to any supplementing of the record.
We therefore will consider the transcriptions to the extent that the Government did
not object—as Thomas requested—but otherwise deny Thomas’s motion to
supplement the record.

                                         -3-
drugs, drug paraphernalia, Thomas’s Samsung Galaxy J1 cellphone, and his
Samsung Galaxy Note 8 tablet. Officers also discovered G.B., an alleged sex-
trafficking victim, in the apartment. Officer Wilshusen interviewed her on the scene.
She described buying heroin from Thomas and having sex with him for heroin when
she did not have money. Later that day, AUSA Jennings filed a criminal complaint
charging Thomas with heroin-related offenses. The complaint made no mention of
Thomas’s sex-trafficking activity.

       In early March 2018, Officer Wilshusen and AUSAs Bruner and Jennings
interviewed G.B. about her involvement with Thomas. She again described how she
obtained heroin from him and that he often used heroin to exploit her. She said that
Thomas had asked to advertise her on Backpage.com and to arrange for her to have
sex with customers in hotels. According to G.B., Thomas explained to her that
potential customers would talk to him and then he would “set it up with the girls.”
Reports of these interviews with G.B. were provided to Thomas during discovery in
the heroin case.

       Relying in part on this interview, Officer Wilshusen obtained a search warrant
for the cellphone and tablet seized from Thomas’s apartment (ostensibly to search
for evidence of drug crimes). In the application for the warrant, Officer Wilshusen
described the controlled drug buys and information learned from G.B., namely that
G.B. stated she had sex with Thomas for heroin and that Thomas had asked if he
could advertise her on Backpage.com as a prostitute.

      The cellphone search revealed evidence of sex trafficking and prostitution.
Based on that evidence, on March 9, AUSA Bruner served a second subpoena to
Backpage.com for records associated with that cellphone number. Backpage.com
provided relevant posts and advertisements from January through February 2018 and
an email address associated with the cellphone number. AUSA Bruner then used
that email address to serve a third subpoena on Backpage.com, yielding more
advertisements linked to Thomas.

                                         -4-
       On March 13, at a preindictment detention hearing for the heroin charges, the
Government (represented by AUSA Jennings) pointed to Thomas’s pending state
human-trafficking charge as a significant reason to deny bond. AUSA Jennings
summarized those allegations against Thomas and stated that “it’s of particular note
that the defendant is alleged to have provided narcotics to this minor as a part of
human trafficking, and here we are again, the defendant has sold narcotics in three
controlled buys.”

      After the detention hearing, AUSA Jennings wrote an internal prosecution
memorandum proposing an indictment for heroin charges. The memorandum
explained that Thomas was arrested on the heroin charges to “get him off the street.”
AUSA Jennings intended to bring the state human-trafficking charge in federal court
“and/or develop a new trafficking case against [Thomas] based on more recent
conduct.” Finally, in a section addressing “additional investigation,” the
memorandum stated, “Analyze phones to gather additional evidence regarding
heroin and/or HT [human trafficking].”

       On March 27, a grand jury returned a five-count indictment for heroin-related
offenses. G.B. was one of the witnesses before the grand jury. She described her
involvement with Thomas like she had to the officers in earlier interviews.
Immediately after the indictment was returned, AUSA Jennings had G.M.—the
alleged victim in Thomas’s pending state charges—appear before the grand jury to
“lock in her testimony.” G.M. testified about Thomas’s sexual exploitation of her.

       The investigation continued. On April 10, DMPD officers obtained a state
search warrant for Thomas’s cellphone seized from his apartment to search for
evidence of sex trafficking. In the application for the warrant, DMPD Officer
Michael Westlake recounted information about Thomas’s trafficking of G.M. and
about Officer Wilshusen’s search of Thomas’s apartment and his cellphone. The
application stated that the earlier search of the cellphone revealed “evidence of
human trafficking and prostitution including outgoing and incoming text messages
detailing multiple instances of human trafficking and prostitution. This evidence

                                         -5-
would be beneficial to Thomas’s human trafficking case and could identify other
potential victims.”

       On May 21, 2018, the district court accepted Thomas’s plea agreement in the
heroin case. For the guilty plea’s factual basis, Thomas admitted that in January and
February 2018 he conspired to distribute heroin. He specifically admitted to
distributing on three occasions in February. He also admitted to having possessed
heroin with intent to distribute on February 28, 2018—the day the search warrant
for his home was executed. Thomas did not admit to sex-trafficking conduct. AUSA
Jennings signed the plea agreement for the Government. There is no indication that
the parties specifically negotiated or discussed the precise meaning of the No Further
Prosecution clause. The district court sentenced Thomas to 48 months’
imprisonment.

       Meanwhile, based on the earlier interviews with G.B., DMPD Officer Michael
Fong interviewed B.B., an alleged associate of Thomas identified by G.B. B.B.
pointed him to K.T., identifying her as a prostitute also involved with Thomas. In
June 2018, K.T. gave a proffer interview with AUSA Bruner and Officer Fong.
Precisely why they interviewed K.T. is debated. The Government asserts that the
interview was conducted as part of an unrelated sex-trafficking case involving two
other suspects. On the other hand, Officer Fong testified that the information he
learned from B.B. led him to speak to K.T. It is undisputed that as a result of the
K.T. proffer interview, Officer Fong searched DMPD records for other complaints
about Thomas. This led him to alleged victim S.A., who had made an earlier report
that Thomas had sexually assaulted her. Officer Fong, along with AUSAs Jennings
and Bruner, then interviewed S.A. about Thomas. In that interview, S.A. identified
alleged victim J.W. and suggested that officers contact her because she had also been
beaten and trafficked by Thomas.

      Following these efforts, DMPD Officer Carney (who was involved with the
Thomas investigation at the peak of the heroin case and who participated in the
February 2018 apartment search) eventually managed to interview J.W. in 2019.

                                         -6-
J.W. also implicated Thomas in heroin distribution and sex trafficking and identified
another alleged victim, E.J. Officer Carney interviewed E.J. in 2020. In that
interview, Officer Carney described the investigation:

      Once we did the heroin case and we started to talk to people, there were
      a couple very, very brave young women who, while we were doing the
      heroin case, kind of told us what was going on, and what happened to
      them, and how he operated. And so ever since then, we have been
      working on tracking down people who we knew that he was involved
      with . . . . [A]nd we fully anticipate to prosecute him in federal court
      for all of the sex crimes that he committed . . . .

When E.J. asked how Officer Carney had gotten her name, he answered,

      from investigating [Thomas] and we have his cell phones from a couple
      of years ago of when we recovered them. . . . And to be honest, the
      focus was at first a kind of drug investigation, and then it was like, holy
      cow, there is way more to this. And . . . so, yes, I knew a little bit about
      you from digging into his past and working this case and, then, I’ll be
      honest with you, yes a couple of the girls mentioned, they didn’t know
      exactly who you were, but a couple of girls mentioned you.

      Officer Carney’s continuing efforts led to three other alleged victims: L.G.,
K.D., and N.L. His reports state that he located each victim’s contact information
in Thomas’s cellphone that was obtained during the February 2018 apartment search.

       That brings us to the current prosecution and appeal. In August 2020, Thomas
was indicted on seventeen counts related to sex trafficking, facilitating prostitution,
and drug offenses. The seventeen counts corresponded to the eight alleged victims
identified above (G.M., G.B., S.A., J.W., E.J., L.G., K.D., and N.L.), some of whom
were associated with multiple counts. Count 17 was not tied to a particular victim
but alleged a violation of the Travel Act for facilitating prostitution. See 18 U.S.C.
§ 1952(a)(3)(A). It appears to apply to conduct involving several or all the victims.
Thomas moved to dismiss the indictment arguing that all counts arose from or
directly related to the 2018 investigation and were therefore barred by the 2018 plea

                                          -7-
agreement. Before the motion was resolved, the Government voluntarily dismissed
Count 13, related to Thomas providing heroin to G.M., and Count 15, related to
Thomas providing heroin to G.B. Thus, fifteen counts remained for the district
court’s consideration on the motion to dismiss.

       The district court entered a preliminary order finding that the language of the
plea agreement’s No Further Prosecution clause—“any other federal criminal
offense arising from or directly relating to this investigation”—was ambiguous. It
then held an evidentiary hearing to admit parol evidence to determine the scope of
that clause. The hearing focused on testimony from the attorneys involved in
negotiating the 2018 plea agreement, followed by argument on the motion. Arguing
for the Government, AUSA Bruner emphasized that the inquiry should focus on the
defendant’s “reasonable belief” of the No Further Prosecution clause’s scope and
that Thomas could not have reasonably believed that the heroin plea deal would
shield him against charges for sex trafficking of unrelated victims. Thomas’s
counsel emphasized the plain language of the plea agreement and that any
ambiguities should be construed against the Government.

       The district court determined that the plea agreement’s reference to “this
investigation” meant only a separate heroin investigation. The court characterized
it as a standard drug case consisting of three controlled buys and the search of
Thomas’s apartment. The court then concluded that a reasonable person in
Thomas’s position would have believed that “this investigation” referred only to the
information gathered by the Government related to Thomas’s drug activity because
the complaint, indictment, and guilty-plea factual basis involved only drug offenses
and facts, with no mention of sex-trafficking. As a result, the court denied Thomas’s
motion as to all counts but one, Count 14, which involved G.B. (who was found in
Thomas’s apartment when it was searched). Ultimately, Thomas pleaded guilty in
2021 to some of the remaining counts (1, 2, 3, 8, 11, and 16, involving victims E.J.,
S.A., J.W., L.G., K.D., and N.L., respectively) in exchange for the Government’s
dismissal of the others. He reserved his right to appeal the denial of his motion to
dismiss the indictment with respect to the undismissed fourteen counts. See Fed. R.

                                         -8-
Crim. P. 11(a)(2). Thomas was sentenced to life imprisonment for each count, to be
served concurrently.

                                         II.

       We review a district court’s interpretation and enforcement of a plea
agreement de novo. United States v. Collins, 25 F.4th 1097, 1100 (8th Cir. 2022).
“We generally interpret the meaning of the terms in the agreement according to basic
principles of contract law.” Id. (brackets omitted). This involves “discern[ing] the
intent of the parties as expressed in the plain language of the agreement when viewed
as a whole.” United States v. Lara-Ruiz, 681 F.3d 914, 919 (8th Cir. 2012). But
“[a]pplication of these contract principles is tempered by the constitutional
implications of a plea agreement.” Margalli-Olvera v. INS, 43 F.3d 345, 351 (8th
Cir. 1994) (interpreting a prior plea agreement’s effect on later immigration
proceedings). Allowing the government to breach a promise that induced a guilty
plea violates due process. Collins, 25 F.4th at 1100-01. Accordingly, we construe
ambiguities in a plea agreement against the government. Id.

                                         A.

       The No Further Prosecution clause provides, in relevant part: “The
Government agrees that Defendant will not be charged in the Southern District of
Iowa with any other federal criminal offense arising from or directly relating to this
investigation.” The district court concluded that “this investigation” was ambiguous,
referring either to the specific facts supporting the heroin-related charges or to the
full set of facts learned by the Government from investigating Thomas in pursuing
those charges. We disagree.

      The plea agreement does not expressly define “this investigation,” so we look
to its ordinary, natural meaning. See Margalli-Olvera, 43 F.3d at 352.
“Investigation implies a systematic tracking down of facts and circumstances,
typically from a variety of sources, in hopes of putting together an account that

                                         -9-
answers, as far as possible, what happened.” Investigation; Inquiry; Inquisition;
Probe, Garner’s Dictionary of Legal Usage (3d ed. 2011). Similarly, Black’s Law
Dictionary defines an investigation as “[t]he activity of trying to find out the truth
about something, such as a crime, accident, or historical issue.” See Investigation,
Black’s Law Dictionary (11th ed. 2019). These definitions are quite encompassing
and capture an unambiguous, familiar concept. In application, that concept,
combined with the modifier “this,” directs us to examine the particular “activity” or
“systematic tracking down” of the particular “facts and circumstances” at issue.
Rightly so. Criminal investigations are as varied as defendants’ offenses and modi
operandi. Thus, determining the scope of “this investigation” in the No Further
Prosecution clause necessarily entails looking to the facts of that investigation. See
Lara-Ruiz, 681 F.3d at 921 (applying the plain meaning of “physical violence” to
the offenses at issue in the case).

       On these facts, “this investigation” refers to the single investigation into
Thomas that encompassed his intertwined heroin and sex-trafficking conduct
leading up to his May 2018 guilty plea. Indeed, discovery materials shared with
Thomas as well as the Government’s arguments at the detention hearing included
references to sex-trafficking and specific facts that could support federal sex-
trafficking charges. To pluck specific facts out of the investigation to arrive at a
narrower “investigation” goes against the ordinary meaning of the term, which
contemplates a weaving together of facts “from a variety of sources” to “put[]
together an account” or “find out the truth” about “what happened.” And yet the
Government takes just such a piecemeal approach. It treats facts related to Thomas’s
heroin offenses as belonging to one investigation and facts related to his sex
trafficking as belonging to another, even if those facts were obtained from the same
witness interviews or from the same searches and seizures of the same devices. In
its view, “this investigation” unambiguously refers to a separate heroin investigation.

      But the record shows that Thomas’s heroin distribution and sex trafficking
were intertwined. Thomas provided heroin to his sex-trafficking victims and used
the drug’s addictive qualities to seduce, control, and exploit them. Our opinion in

                                         -10-
Thomas’s 2019 appeal of his sentence for the heroin charge recognized as much.
See United States v. Thomas, 777 F. App’x 180, 180-81 (8th Cir. 2019) (per curiam)
(“We further conclude that the district court did not err in imposing an above-
Guidelines sentence based on Thomas’s prostitution activities, which the court found
were ‘inextricably intertwined’ with his drug offense.”). Beginning with the
allegations from G.M. and G.B. and the devices seized from the apartment search,
state and federal officers working in tandem built a federal sex-trafficking case
against Thomas and used the heroin case to “get him off the streets” in the meantime.
In short, “this investigation” refers to the one investigation into Thomas, which
reflected the inextricably intertwined nature of his conduct.

       Accordingly, we are not persuaded by the Government’s Ninth Circuit
authority interpreting the following no-further-prosecution clause in a plea
agreement: “The government agrees that no other charges will be filed against
defendant in connection with this investigation.” See United States v. Clark, 218
F.3d 1092, 1094 (9th Cir. 2000). The Ninth Circuit concluded, based on the four
corners of the plea agreement, that “this investigation” unambiguously referred only
to the investigation of the defendant’s postal robberies and not an unrelated,
unmentioned, and uncharged burglary. Id. at 1095-97. Yet Clark contained no
specific discussion of the meaning of “investigation” and how it is inherently derived
from the conduct of investigators. See id. at 1095-96. We find such analysis
necessary here. And crucially, in Clark there was “very little evidence of a link
between investigations of the two different crimes.” Id. at 1094. In Thomas’s case,
the link is unmistakable—the record shows one, overarching investigation.

       Our reading of “this investigation” also gives full effect to the various terms
of the plea agreement. Cf. Harris v. The Epoch Grp., L.C., 357 F.3d 822, 825 (8th
Cir. 2004) (“[U]nder federal common law a contract should be interpreted as to give
meaning to all of its terms—presuming that every provision was intended to
accomplish some purpose, and that none are deemed superfluous.” (internal
quotation marks omitted)); see United States v. Hamdi, 432 F.3d 115, 123-24 (2d
Cir. 2005) (applying to a plea agreement the principle of contract law preferring an

                                        -11-
interpretation that does not leave a portion of the contract superfluous). In addition
to “this investigation,” the agreement refers to “charges” and “offenses.” These are
distinct terms with distinct meanings. See United States v. Transfiguracion, 442
F.3d 1222, 1234 & n.20 (9th Cir. 2006). Paragraph 2 of the plea agreement addresses
the charges to be dismissed, whereas paragraph 3 promises no further prosecution
of offenses “arising from or directly relating to” this investigation. Thus, to read
“this investigation” as extending no further than the related heroin charges or
offenses risks rendering superfluous a key part of the agreement. See United States
v. McLaughlin, 813 F.3d 202, 204 (4th Cir. 2016). At the very least, it strains a core
contractual principle that different language used to address similar issues generally
carries different meaning. See Larson v. Nationwide Agribusiness Ins., 739 F.3d
1143, 1147-48 (8th Cir. 2014) (interpreting Minnesota law); Owners Ins. v. Fid. &
Deposit Co. of Md., 41 F.4th 956, 959 (8th Cir. 2022) (applying Larson’s reasoning
to Missouri contract); see also Antonin Scalia and Bryan A. Garner, Reading Law:
The Interpretation of Legal Texts 170 (2012) (“[A] material variation in terms
suggests a variation in meaning.”). Without compelling reasons to disregard these
differences, we are not persuaded by the Government’s narrow reading of the plea
agreement.

        Moreover, even if the facts here left the phrase “this investigation” unclear,
the district court was “bound to construe the agreement against the Government”—
that is, in the broad sense described above rather than the narrow sense of trying to
separate intertwined aspects of the investigation based on the prosecution’s
subjective goals. See United States v. Lewis, 673 F.3d 758, 763 (8th Cir. 2011).
After all, the Government was in the best position to draft a narrower or more precise
agreement. See United States v. Harvey, 791 F.2d 294, 301 (4th Cir. 1986) (noting
that the government bears the “primary responsibility for insuring precision in [plea]
agreement[s]”). Consider how the Government might have easily limited its side of
the bargain. It could have promised no further prosecution “for the specific conduct
described in the indictment or statement of facts.” See United States v. Jordan, 509
F.3d 191, 196 (4th Cir. 2007); see also United States v. McClure, 854 F.3d 789, 795
(5th Cir. 2017) (noting that the plea agreement’s promise was limited to offenses

                                        -12-
related to the conduct supporting the guilty plea rather than the government’s
investigation into that conduct). Or the Government might have limited the range
of offenses that it agreed not to prosecute by using language like “the defendant will
not be charged with any other drug offense” or “any other Title 21 offense.” See
Lara-Ruiz, 681 F.3d at 917. And above all, the Government could have expressly
excepted sexual-exploitation offenses from the plea agreement. Indeed, the No
Further Prosecution clause already contained three express exceptions. The lack of
a fourth to address the looming sex-trafficking offenses further supports the plainly
broad scope of the clause. If Thomas would have rejected these narrower terms, the
Government could have proceeded to trial. As it is, the plea agreement did not
include such limitations, and we are not persuaded by the Government’s attempt to
insert them after the fact. Thus, we disagree with the district court that “this
investigation” was limited to a heroin-related subset of the overall investigation into
Thomas.

                                          B.

       Having resolved the reach of “this investigation,” the question then is whether
any of the fourteen undismissed counts arose from or were directly related to it. The
parties largely agree about what “arising from” and “directly relating to” mean. In
this context, to arise is “[t]o originate; to stem (from),” or “[t]o result (from).” See
Arise, Black’s Law Dictionary. It has a broad meaning. See McClure, 854 F.3d at
795 (implying that “arising out of” is broader than “based upon”). “Relating to” is
similarly broad. Cf. Morales v. Trans World Airlines, Inc., 504 U.S. 374, 383 (1992)
(interpreting “relating to” in a federal preemption statute). The parties acknowledge
that the word directly narrows “relating to” to mean in a “straightforward” manner.
See Directly, Black’s Law Dictionary. Context also informs the reach of “arising
from” and “directly relating to.” The No Further Prosecution clause covers “any
other federal criminal offense.” The words “any other” imply that such offenses
may arise from or directly relate to the investigation in various manners and
directions. Thus, the Government’s promise sweeps broadly and stands in contrast

                                         -13-
with the more constrained “in connection with” language of the plea agreement in
Clark. See 218 F.3d at 1094.

       We conclude that all undismissed counts “ar[ose] from or directly relat[ed] to
this investigation.” The same investigation that led to the heroin charges led to the
sex-trafficking charges. The two cases shared prosecutors, DMPD officers,
witnesses, and subject matter—Thomas’s heroin distribution and sex trafficking.
Early 2018 victim statements, cellphone searches, and subpoenaed records gave rise
to later-identified alleged sex-trafficking victims and corroborated their accounts.
The 2020 seventeen-count indictment was therefore the outgrowth of efforts rooted
in that early 2018 investigation. Some counts may bear a stronger connection to that
investigation than others, but “arising from” and “directly relating to” are
sufficiently broad to encompass them all.

       To start with the obvious, we find it noteworthy that the indictment included
two later-dismissed counts (14 and 15) clearly within the plea agreement’s scope.
They both involved Thomas’s exploitation of G.B., one for heroin and one for sex-
trafficking. G.B. was discovered during the heroin search of Thomas’s apartment.
These counts were clearly precluded by the 2018 plea agreement. Yet the
Government nonetheless brought them. It then dismissed the heroin count
voluntarily but left the sex-trafficking count. The district court was right to dismiss
that sex-trafficking count. The fact that the Government even brought these two
counts highlights its misinterpretation and strained reading of the No Further
Prosecution clause.

         The fourteen undismissed counts present a somewhat closer issue, but they
still straightforwardly arise from or directly relate to the 2018 investigation. For
Count 12 associated with G.M., the Government became aware of the information
supporting this charge during the height of the heroin case when DMPD Officer
Wilshusen notified the U.S. Attorney’s Office that he had a suspect for heroin
charges, who also happened to have a pending state charge for human trafficking.
The Government then used the allegations against Thomas at his preindictment

                                         -14-
detention hearing. At that time there was no federal sex-trafficking case against
Thomas. It would have been plain to all involved—including Thomas during the
hearing—that the Government had information supporting such a case and was
employing it in the heroin case to keep Thomas off the streets. The details about
G.M. cannot be cabined to some separate investigation involving separate people
and departments when the record shows otherwise.

       As for Counts 1 and 3 through 7, associated with E.J. and J.W., they arose
from and directly relate to S.A.’s interview with AUSAs Jennings and Bruner and
Officer Fong. S.A. identified J.W., who in turn identified E.J. As for S.A. herself,
the alleged victim of Count 2, Officer Fong acknowledged that he became aware of
her when his participation in the proffer interview with K.T. prompted him to search
for reports about Thomas. Indeed, in a later report, Officer Fong recognized that the
sex-trafficking case grew, at least in part, from the early investigation into Thomas:
“During 2017 and 2018, through these investigations and through parallel drug and
sex trafficking investigations I have received information Thomas has been involved
in sexual assault and sex trafficking.” These seven counts therefore arose from and
directly related to the 2018 investigation.

       For Counts 8 through 11 and 16, involving L.G., K.D., and N.L., the link to
the investigation is straightforward. Officer Carney’s reports state that he located
each victim’s contact information in Thomas’s cellphone that was obtained during
the February 2018 apartment search. Indeed, the Government acknowledges that
N.L. was located through information from Thomas’s cellphone and tablet seized in
2018. The Government maintains, however, that alleged victims L.G. and K.D. were
not identified through any information learned from the ongoing investigation rooted
in 2018 but through information provided by witnesses first interviewed in 2020.
Beyond these bare claims in the Government’s opposition brief before the district
court, there is no record tracing their separate, independent connection to Thomas’s
crimes. Further, the Government acknowledges that Backpage.com records linked
to Thomas and obtained from the earlier subpoenas corroborated K.D.’s and N.L.’s
accounts. As for L.G., the Government is more vague: “Additional investigation

                                        -15-
such as phone records and arrest reports provided further information that
corroborated her account.” But this vagueness is not enough to overcome Officer
Carney’s reports about finding her contact information in Thomas’s cellphone.

       That leaves Count 17 involving the Travel Act. It is not tied to a particular
victim. There is no indication that the charge relates to Thomas’s conduct separate
or apart from that which formed the basis for the other counts. We see no reason
why it too is not barred by the plea agreement as arising from or directly relating to
the investigation in early 2018.

                             *            *            *

       This is a broad result. But it is not surprising. The plea agreement combines
the broad language of “arising from or directly relating to” with the broad scope of
“this investigation.” Against this result, the Government points to the reasonable-
belief principle, see United States v. Olesen, 920 F.2d 538, 541 n.1 (8th Cir. 1990),
and argues that Thomas could not have reasonably believed that he could not be
prosecuted for these sex-trafficking offenses. The district court took the
Government’s view and concluded that “[g]iven the government’s policy requiring
a plea to the greatest charge, neither a reasonable defense attorney or an AUSA
would expect to resolve a human trafficking charge by a sentence forty percent or
less of the statutory mandatory minimum.” United States v. Thomas, No. 4:20-cr-
00118, Doc. 59 at 18 (S.D. Iowa Feb. 2, 2021). In hindsight, that may be. But we
cannot ignore or reject the plain language of the plea agreement and the full scope
of the investigation merely because, in hindsight, we think Thomas received too
good of a deal. See United States v. Rewis, 969 F.2d 985, 988 (11th Cir. 1992) (“It
is not our function to determine if the government made a wise choice in entering
into such an agreement, we merely must ensure that plea agreements are followed.”);
see also Dunn v. Colleran, 247 F.3d 450, 464 (3d Cir. 2001) (noting that a prosecutor
may not “unilaterally repudiate his or her promises because honoring them becomes
distasteful”). Moreover, as we have emphasized here, discovery materials shared
with Thomas during the 2018 heroin prosecution included express references to sex-

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trafficking and specific facts supporting potential sex-trafficking charges.3 The
Government would have the reasonable-belief principle do more work than the plea
agreement’s language can bear—limiting the No Further Prosecution clause’s
plainly broad terms to the narrower scope of different terms in the plea agreement
like “indictment,” “offense,” or “charges” because, in its view, that is what the plea
agreement was really about. We reject that invitation and hold the Government to a
greater degree of responsibility than the defendant for the plea agreement’s
purported imprecisions or ambiguities. See United States v. Bowman, 634 F.3d 357,
360-61 (6th Cir. 2011).

      In sum, we conclude that the undismissed counts were squarely barred by the
plea agreement’s broad No Further Prosecution clause. We emphasize that this
holding is on the facts here—the language of Thomas’s plea agreement and the
nature of the investigation into his inextricably intertwined drug and sex-trafficking
conduct. Other plea agreements that employ similar language must be construed
according to their respective factual contexts.

                                         III.

       Finally, we turn to the question of the appropriate remedy given the
Government’s breach of the 2018 plea agreement. There are two potential remedies:
specific performance of that agreement or withdrawal of the guilty plea secured by
it. See Olesen, 920 F.2d at 540. Ordinarily, we would remand the question of
remedy so that the district court can address it in the first instance. See Collins, 25
F.4th at 1102. Yet where the defendant has requested specific performance, we have
sometimes granted it ourselves. See, e.g., Margalli-Olvera, 43 F.3d at 354-55;
United States v. Mosley, 505 F.3d 804, 812 (8th Cir. 2007); United States v. Van

      3
       Although we find the plea agreement’s language to be unambiguous and
therefore need not consider parol evidence, we note that Thomas’s counsel
understood that the Government would leave the sex-trafficking prosecution related
to G.M. with the State of Iowa. Thomas’s counsel also understood “this
investigation” to include the information provided by the Government in discovery.

                                         -17-
Thournout, 100 F.3d 590, 596 (8th Cir. 1996). Where the defendant requests
withdrawal of his plea rather than specific performance, we are more inclined to
remand the choice to the district court’s discretion. See United States v. Swisshelm,
848 F.3d 1157, 1159 (8th Cir. 2017). But specific performance remains the preferred
remedy. Margalli-Olvera, 43 F.3d at 354-55. Thomas seeks specific performance
in the form of dismissal of the indictment and vacatur of his conviction. In his case,
withdrawal of the 2018 guilty plea in the heroin case would be “an empty remedy”
because Thomas has already served his prison sentence for that offense. See Lara-
Ruiz, 681 F.3d at 923; see Transfiguracion, 442 F.3d at 1236 (affirming specific
performance of plea agreement’s no-further-prosecution clause where the
government’s breach and prejudice to defendant could not be undone). We therefore
turn our focus to Thomas’s request for specific performance.

       We consider three factors in considering a defendant’s demand for specific
performance of a plea agreement after the defendant has pleaded guilty: (1) the
possible prejudice to the defendant, (2) the conduct of the government, and (3) the
public interest. Hall v. Luebbers, 341 F.3d 706, 715 (8th Cir. 2003). “Prejudice to
the defendant is the most important.” Margalli-Olvera, 43 F.3d at 355. Here, the
prejudice is clear. Thomas pleaded guilty in 2018 to one drug offense in exchange
for the Government dismissing the remaining drug offenses and promising not to
bring further charges arising from or directly relating to the investigation. The
Government reneged on that promise by pursuing the sex-trafficking prosecution,
which relied on facts that were part of and arose out of the 2018 investigation. As a
result, Thomas faced charges he would not otherwise have faced had the
Government stuck to its bargain. His 2021 guilty plea therefore was premised on a
nullity. Further, the prosecution’s breach of the plea agreement implicates “the
honor of the government, public confidence in the fair administration of justice, and
the effective administration of justice in a federal scheme of government.” See
Swisshelm, 848 F.3d at 1159. “Plea agreements are an essential component of the
administration of justice . . . .” United States v. Mitchell, 136 F.3d 1192, 1194 (8th
Cir. 1998). On the other hand, the public also has an interest in safety from criminal
behavior and in the prosecution of crimes. But that does not outweigh constitutional

                                        -18-
due-process interests, and the Government’s breach of the plea agreement violated
Thomas’s due-process rights. See Collins, 25 F.4th at 1100 (“The government’s
breach of a promise that induced a guilty plea violates due process.”). Specific
performance is therefore warranted and requires that we reverse the district court’s
denial of the motion to dismiss the indictment and vacate Thomas’s conviction.

                                        IV.

      We do not take lightly vacating a conviction and concurrent life sentences on
such heinous offenses. Yet it is our duty to hold the Government to the bargain it
made. Thus, for the foregoing reasons, we reverse the district court’s denial of
Thomas’s motion to dismiss the indictment with respect to the undismissed fourteen
counts and vacate his conviction.
                       ______________________________

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