United States v. Juan Adame-Hernandez , 763 F.3d 818 ( 2014 )

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 12-1268
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
JUAN CARLOS ADAME-HERNANDEZ,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Southern District of Indiana, Indianapolis Division.
No. 1:10-cr-0003-SEB-KPF-1 — Sarah Evans Barker, Judge.
____________________
ARGUED MAY 29, 2013 — DECIDED AUGUST 18, 2014
____________________
Before WOOD, Chief Judge, and BAUER and TINDER, Circuit
Judges.
TINDER, Circuit Judge. This appeal arises from the same
underlying criminal case that we address in another opinion
issued today, United States v. Kenneth Jones, Ramone Mockabee,
Devon Young, and Elisha Drake, Nos. 11-2267, 11-2288, 11-2535
& 11-2687. Defendant-Appellant Juan Carlos Adame-
Hernandez (Adame) sold cocaine to Dominic Robinson and
was thereby an upstream source for the cocaine distributed
2 No. 12-1268
by the Mockabee organization discussed at length in that
opinion. Adame’s appeal had been consolidated with the
others but because his appeal arises from substantially dif-
ferent circumstances that are unique to him, we have with-
drawn the consolidation of his appeal to address it separate-
ly in this opinion. Adame’s appeal focuses exclusively on a
plea bargain gone awry, and we will therefore recite only the
facts relevant to his plea.
BACKGROUND
In 2010, Adame was charged along with numerous other
defendants with a criminal drug conspiracy as well as co-
caine distribution and illegal reentry of a previously deport-
ed alien subsequent to a conviction for the commission of an
aggravated felony. See 21 U.S.C. §§ 841(a)(1), 846; 8 U.S.C. §
1326(a). He was later charged with the same offenses in a
superseding indictment.
On January 3, 2011, having entered into a binding, writ-
ten plea agreement with the government under Rule
11(c)(1)(C) of the Federal Rules of Criminal Procedure,
Adame filed a petition to enter a plea of guilty to the con-
spiracy charged in Count One of the superseding indict-
ment. As part of the agreement, the parties stipulated to a
base offense level of 38, pursuant to U.S.S.G. § 2D1.1(c)(1).
The government agreed not to file an information pursuant
to 21 U.S.C. § 851, which would have increased Adame’s
mandatory minimum sentence because of a prior felony
drug conviction. The resulting advisory guidelines range
was 188-235 months, and the parties agreed “that a sentence
of 204 months’ imprisonment and a term of supervised re-
lease and fine as imposed by the Court is the appropriate
disposition of the case.” The agreement reserved to the par-
No. 12-1268 3
ties “the right to present evidence and arguments on all sen-
tencing issues not specifically addressed in this Plea Agree-
ment.” Counts Two and Three of the superseding indict-
ment, charging cocaine distribution and illegal re-entry, re-
spectively, were also to be dismissed as a part of the deal.
On that same date, the district court held a change of plea
hearing. The court addressed Adame personally and dis-
cussed the nature of Count One, the possible sentencing
range, and his understanding that, by pleading guilty, he
was waiving certain constitutional rights. See Fed. R. Crim.
P. 11(b)(1). The court was careful to call Adame’s attention to
the plea agreement and the fact that it was binding as a rule
“11(c)(1)(C) agreement. And that’s a binding plea agreement
between you and the Government as to a specific sentence.”
Plea Hrg. Tr. 15, Jan. 3, 2011. The court explained, “[E]very
part of it is binding. It’s like a contract between you and the
Government lawyers. It’s binding on you, and it’s binding
on them.” Id. at 14. The agreement explains what would
happen if the judge decided not to accept the plea:
The parties to this agreement acknowledge and un-
derstand that while the Court is not a party to this
agreement, in the event the Court determines the sen-
tence should not be as set forth herein and therefore
rejects the plea agreement, the Court will so advise
the defendant, who may then withdraw his plea of
guilty, pursuant to Fed. R. Crim. P. 11(c)(4) [sic, the
correct provision is Rule 11(c)(5)].
The court also discussed whether the plea was voluntary.
See Fed. R. Crim. P. 11(b)(2). After the government estab-
lished a factual basis for the plea through the testimony of
Detective Ryan Clark, Adame confirmed that the facts prof-
4 No. 12-1268
fered against him were true and pleaded guilty. The court
accepted his plea and adjudged him guilty of the conspiracy
charged in Count One of the superseding indictment. The
court explained that its next task was to determine a sen-
tence, and that the probation office had to prepare a presen-
tence investigation report, which the court would use “along
with [the] plea agreement that has the specific sentence bar-
gained for, to decide what a reasonable sentence is … .” Id. at
36.
As expected, the probation office prepared a presentence
investigation report. The report recommended that Adame
be found responsible for more than 150 kilograms of cocaine,
resulting in a base offense level of 38. Adame raised two ob-
jections to the report: he denied that he personally delivered
over 150 kilograms of cocaine, and he objected to a fact un-
derlying an adjustment for his aggravated role in the of-
fense.
About six months after the guilty plea, on July 7, 2011,
Adame returned to the district court for sentencing. The rec-
ord does not disclose that he had any prior notice that any-
thing other than sentencing would occur at that hearing;
there is no indication that he knew the government would
claim he had breached the plea agreement. At the hearing,
defense counsel asserted that while Adame would maintain
that he personally delivered less than the amount of cocaine
attributed to him in the presentence report, he understood
that he could be held accountable for amounts based on his
involvement in the conspiracy. The prosecutor argued that
Adame had thereby objected to the base offense level stipu-
lated to in the plea agreement and asserted that this consti-
tuted grounds to find a breach of the plea agreement. The
No. 12-1268 5
prosecutor also asserted that the trial evidence would estab-
lish that Adame personally distributed over 150 kilograms of
powder cocaine: a government witness would testify that he
personally received more than that amount from Adame.
The prosecutor questioned whether Adame had accepted
responsibility for his conduct and asked the court to set
aside the plea and set the case for trial. Notwithstanding this
request, the prosecutor expressed uncertainty over whether
the alleged breach was material, at one point stating, “Is that
breach material? I don’t know.” The defense counsel argued
that Adame’s position did not amount to a breach of the plea
agreement and did not affect the sentence. Sent. Tr. 16, July
7, 2011. (“[R]egardless of whether we win these points or
lose these points, it doesn’t change the number of months
that are recommended in the plea.”) Yet when questioned
whether the plea agreement included a stipulation to the of-
fense level that involved a drug quantity calculation, defense
counsel responded in the affirmative.
The district court stated that if the defendant “[is] back-
ing off the quantity, that seems to me to be inconsistent with
your stipulation.” Id. at 18. The court added that it seemed
that Adame was taking a position that was “inconsistent
with the bargain that he struck with the government.” Id.Then the district court turned to whether the agreed-upon
sentence was reasonable, and connected that issue with the
government’s claim of breach:
Unaddressed at this point is whether under 3553(a)
this is a sentence that the Court could accept. I’m the
third-party to this agreement, … and I have my own
difficulties with this agreement because, for one
thing, Mr. Adame comes in here close to the end of
6 No. 12-1268
the proceedings—and I know what everybody got be-
cause I meted out those sentences. For him to have
been in the leadership role that he was in in this con-
spiracy and a supplier of such a huge amount of co-
caine, given the other sentences, I don’t know that 204
months is something that I can accept either.
So … the appropriate and well advised position is to
note the breach, and withdraw the Court’s finding of
guilty in accordance with this plea agreement, and set
the matter for trial and return to the not guilty plea
that was originally entered for the defendant.
Id. at 20. The court concluded that the agreed sentence was
“not consistent with the other sentences that have been met-
ed out given the relative culpability of the defendants,” a
factor under 18 U.S.C. § 3553(a), and then reiterated that
“besides the breach, the Court views the 204 month sentence
[as] disparate [from the sentences of co-defendants]. So on
my own findings sua sponte I’ll reject the plea agreement.”
Id. at 21. At the end of the hearing, Adame asked whether he
could abandon his objections to the presentence report and
proceed with sentencing under the plea agreement, but the
court denied his request, saying, “[I]t’s too late.” Id.Immediately after vacating its acceptance of the guilty
plea, the district judge reset Adame’s case for trial in October
2011. However, on August 24th, the Grand Jury returned a
second superseding indictment against Adame. This version
of the indictment also contained three counts, with Counts
Two and Three being identical to the prior iterations. Count
One also described a cocaine distribution conspiracy, similar
to at least a part of the conspiracy described in the two prior
versions of that charge. However, the conspiracy count in
No. 12-1268 7
the second superseding indictment focused on Adame’s dis-
tribution of large quantities of powder cocaine down the
chain of distribution, and it omitted much detail from the
first version of Count One concerning Mockabee’s subse-
quent redistribution of crack cocaine through the Indianapo-
lis conspirators. Nonetheless, the government does not con-
tend that the conspiracy charged in the second superseding
indictment is different from the one previously alleged; and
as noted below, a subsequent factual presentation by Detec-
tive Clark makes clear that the conspiracy charged in the
second superseding indictment was the same one to which
Adame had earlier pleaded guilty.
Adame filed a written waiver of an initial appearance
and formal arraignment on the second superseding indict-
ment. It is important to note that Adame’s waiver does not
contain a plea to the charges in the second superseding in-
dictment, despite the fact that the form of such waivers post-
ed on the district court’s web site suggests that the waiver
contain the language: “I hereby enter a formal plea of not
guilty to the Superseding Indictment.” 1
Shortly before the reinstated trial date, on October 3rd,
Adame filed a document entitled “Renewed Petition to Enter
a Plea of Guilty,” which was followed two days later by a
document entitled “Amended Renewed Petition to Enter a
Plea of Guilty.” The only difference between the documents
was that the first one only referred to Count One, whereas
the amended one also included penalty information about
Count Three. The amended petition has many appearances
1 The form is available online at
http://www.insd.uscourts.gov/forms/waiver-initial-appearance.
8 No. 12-1268
of a form petition that appears to be in circulation among the
criminal bar in that district. 2 This petition discusses routine
matters such as the procedures involved in entering a guilty
plea, the penalties faced, and the rights waived by the plea.
However, the petition filed by Adame in October 2011
contains certain individualized language that appears to
have been drafted specifically for his case. The first clue is
that it is entitled a “renewed” petition. Then the text of
Adame’s petition begins by stating that he had previously
entered a plea agreement pursuant to Rule 11(c)(1)(C) on
January 3rd, the same agreement that was rejected by the
district court in July. It also indicates that Adame had been
advised and understood that “the Court is not required to
follow the plea agreement and has provided me the oppor-
tunity to withdraw the plea; and that if the plea is not with-
drawn, the Court may dispose of the case less favorably to-
ward me than the plea contemplated.” And rather than indi-
cating that he desired to enter a guilty plea to the new, sec-
ond superseding indictment, the petition states that Adame
did not “wish to withdraw his guilty plea” and requested
that the matter be set for a sentencing hearing.
At the hearing on October 5th, the district court again
addressed Adame personally, discussing the charges against
him and the maximum penalties. But there was some confu-
2 We say that because a similar form of petition was used by other de-
fendants who pleaded guilty in this case, see, e.g., United States v. Dominic
Robinson, No. 1:10-cr-00003-SEB-DML-2, ECF No. 1000; United States v.
Ramone Mockabee, No. 1:10-cr-00003-SEB-DML-3, ECF No. 651; United
States v. Seron Poole, No. 1:10-cr-00003-SEB-DML-5, ECF No. 539; and in-
deed, was used by Adame in his original petition to enter a plea of
guilty, see ECF No. 675.
No. 12-1268 9
sion. The judge, noting what she described as a “convoluted
or complicated procedural history” of the case, initially indi-
cated that even though Adame had previously entered a
guilty plea, she “withdrew the plea” because he had not
been “entirely accepting of the facts the government intend-
ed to prove at trial.” Plea Hrg. Tr. 4, Oct. 5, 2011. That much
was a correct recitation of what happened. But later the
judge indicated that she had “refused to accept his plea” to
the prior indictment. Id. at 6. Despite that description, the
judge began an explanation of the plea agreement under
Rule 11(c)(1)(C), stating that a recommendation of a 204-
month sentence would be made, and that if that sentence
was imposed, Adame would give up his right to appeal the
sentence. Government counsel promptly corrected the judge
to remind her that the 11(c)(1)(C) agreement had been reject-
ed. Id. at 8. But even with that reminder, the confusion con-
tinued because the judge then referred to a plea agreement
that had been filed on the morning of the hearing. Id.at 9. But
there was no such agreement—the only document filed was
the Amended Renewed Petition to Enter a Plea of Guilty.
Nonetheless, the court continued to question Adame
about the petition as though it was an agreement, id. at 10,
and then proceeded through what was a fairly standard
Rule 11 colloquy otherwise. It should be noted, though, that
Adame was given a rather jumbled explanation of his appel-
late rights. After confirming with counsel that there was no
appellate waiver, the judge stated:
You have a separate right to appeal, even if you enter
your plea, even if you plead guilty to these charges.
That’s a right to appeal the sentence that’s imposed.
So you have not given up that right, but you have
10 No. 12-1268
given up your right to appeal, we say, the merits of
the case. That means the sufficiency of the Govern-
ment’s evidence that underlies these charges. You’ve
given that right of appeal up. Do you understand
that?
Id. at 13. Despite Adame’s affirmative answer to that ques-
tion, it is hard for us to discern what he may have under-
stood from that portion of the colloquy. The district court
did not explain whether Adame would also waive his right
to appeal a ruling that occurred before his latest plea was
accepted, but did not go to the “merits” of the case or the
sufficiency of the evidence against him.
Detective Clark again provided a factual basis for the
plea to the conspiracy count, which was essentially the same
background that he had presented at the January guilty plea
hearing along with a few additional facts relating to how
Adame came to join the conspiracy. This indicates that, de-
spite differences in the wording of the conspiracy counts be-
tween the second superseding indictment and the prior
ones, they all pertained to the same conspiracy. Clark also
presented a brief synopsis of facts that would support the
illegal re-entry charge in Count Three, facts which had not
been addressed in the earlier hearing. When asked how he
pleaded to Counts One and Three, Adame responded
“guilty.” Announcing that his plea was knowing, voluntary,
and supported by the facts, the court indicated that it was
accepting it and adjudging him guilty of the two counts.
Whereas the original presentence report had recom-
mended a two-level enhancement for Adame’s role in the
offense, the report following the October 2011 plea recom-
mended a three-level enhancement. Under the new calcula-
No. 12-1268 11
tion, Adame was subject to an advisory guidelines range of
262-327 months for Count One. The district court subse-
quently held a sentencing hearing and sentenced him to 300
months in prison on Count One and 240 months on Count
Three, to be served concurrently.
Adame now appeals to this court, seeking the reinstate-
ment of his initial plea agreement along with the joint rec-
ommendation of a 204-month sentence.
ANALYSIS
Adame argues that the district court erred in finding that
he breached the January 3, 2011, plea agreement and in va-
cating his plea. In the alternative, he argues that even if we
conclude that he breached the agreement, he did not commit
a substantial breach. He also maintains that the government
breached the plea agreement by urging the court to vacate
his plea and then encouraging the court to impose a harsher
sentence than the agreed-upon 204 months. 3
He therefore seeks specific performance of his original
plea agreement. The government responds that Adame
waived his right to contest the government’s alleged breach
3 A little more than a week before this sentencing hearing, the govern-
ment filed an information under 21 U.S.C. § 851(a)(1), alleging that
Adame had a prior felony conviction, thereby increasing the mandatory
minimum for Count One from ten to twenty years. Adame did not object
to this filing as untimely and concedes that he forfeited any right to chal-
lenge it. See United States v. Lewis, 597 F.3d 1345, 1347 (7th Cir. 2010).
However, the government had previously agreed not to file such an in-
formation pursuant to its plea agreement with Adame. Because we now
hold the government to the terms of that bargain, the filing of that in-
formation and the resulting increase in the mandatory minimum were
clearly erroneous.
12 No. 12-1268
of the plea agreement by ultimately pleading guilty. It also
argues that, assuming Adame did not waive his right to con-
test the district court’s rejection of his plea agreement, he
breached the agreement and the district court did not abuse
its discretion in rejecting it. Tellingly, the government does
not assert that the district court had the authority to with-
draw Adame’s initial, already-accepted guilty plea over his
objection, which is exactly what happened here.
Generally, “a guilty plea represents a break in the chain
of events which has preceded it in the criminal process.
When a criminal defendant has [entered a guilty plea], he
may not thereafter raise independent claims relating to the
deprivation of constitutional rights that occurred prior to the
entry of the guilty plea.” Tollett v. Henderson, 411 U.S. 258,
267 (1973); see also Gomez v. Berge, 434 F.3d 940, 942 (7th Cir.
2006) (“[A]n unconditional plea of guilty operates as a waiv-
er of all formal defects in the proceedings … that occurred
before the plea was entered.”). The government maintains
that Adame’s guilty plea on October 5 waived any formal
defect occurring before then, including Adame’s right to
contest the district court’s rejection of his plea agreement
and any alleged breach of that agreement by the prosecutor.
We disagree. But before we discuss the waiver issue, we
must review the proceedings chronologically to determine
how this case reached this peculiar posture.
At the January 3 change of plea hearing, Adame pleaded
guilty to the conspiracy charged in Count One of the super-
seding indictment. “A defendant has no absolute right to
have a court accept a guilty plea, and a court may reject such
a plea in the exercise of sound judicial discretion.” United
States v. Ajijola, 584 F.3d 763, 766 (7th Cir. 2009); see also San-
No. 12-1268 13
tobello v. New York, 404 U.S. 257, 262 (1971). Even so, “a court
cannot arbitrarily reject a plea, and must articulate on the
record a ‘sound reason’ for the rejection.” United States v.
Hernandez-Rivas, 513 F.3d 753, 759 (7th Cir. 2008) (citation
omitted). Recognizing that the district court has significant
discretion in accepting or rejecting a guilty plea, we review
its rejection of a guilty plea for an abuse of discretion. Id.But here, the district court accepted Adame’s guilty plea
and adjudged him guilty of the offense charged in Count
One. The acceptance of Adame’s guilty plea was “a judicial
act distinct from the acceptance of the plea agreement itself.”
Wayne R. LaFave et al., 5 Criminal Procedure § 21.4(g) (3d ed.
2008) (quoting In re Ellis, 356 F.3d 1198, 1200 (9th Cir. 2004)
(en banc)). 4 “Once the district court accepts a guilty plea, the
4 The district court accepted the guilty plea, which was made pursuant to
the Rule 11(c)(1)(C) plea agreement. Adame asserts that the court accept-
ed the plea agreement, but the record demonstrates that this is incorrect.
The district court said nothing one way or the other about its acceptance
or rejection of the plea agreement. And after accepting the plea, the court
advised Adame that its next task was to determine a sentence, and that
the probation office had to prepare a presentence investigation report,
which the court would use along with the plea agreement to determine a
reasonable sentence. The court’s intent was confirmed at the July 7 hear-
ing when it explained to Adame that it was going to decide whether to
accept the plea agreement. In fact, when asked whether he understood
that the court would “be deciding whether to accept [the plea] agree-
ment,” Adame answered, “Yes.” Sent. Tr. 9. Adame points to no authori-
ty for the proposition that the court’s statement that it accepted the
guilty plea amounted to acceptance of the plea agreement as well. To the
contrary, “[g]uilty pleas can be accepted while plea agreements are de-
ferred. … [T]he Rules [of Criminal Procedure] nowhere state that the
guilty plea and the plea agreement must be treated identically.” United
States v. Hyde, 520 U.S. 670, 674–77 (1997).
14 No. 12-1268
conditions under which the plea may be withdrawn are gov-
erned exclusively by Rule 11 of the Federal Rules of Criminal
Procedure.” 5 Criminal Procedure § 21.4(g); see also Ellis, 356
F.3d at 1200, 1206.
Nothing in Rule 11 authorizes a district court to with-
draw a defendant’s guilty plea for him. Instead, “[w]here a
district court accepts a plea of guilty pursuant to a plea
agreement, defers acceptance of the agreement itself, and
later rejects the terms of the plea agreement, it must, accord-
ing to the plain language of Rule 11, ‘give the defendant an
opportunity to withdraw the plea.’” 5 Criminal Procedure §
21.4(g) (quoting Ellis, 356 F.3d at 1200 (quoting Fed. R. Crim.
P. 11(c)(5)(B))); see also Hyde, 520 U.S. at 677–78 (“[I]f the
court rejects [the plea agreement], then the agreement is
terminated and the defendant has the right to back out of his
… guilty plea.”); Ellis, 356 F.3d at 1207 (“Rule 11 thus con-
templates that the district court’s rejection of a plea agree-
ment allows the defendant, not the court, to make the next de-
cision with respect to the status of the plea—i.e., whether to
withdraw the plea and proceed to trial, or persist in the plea
and risk a more severe sentence under the Sentencing
Guidelines.”) (emphasis added). Thus, where the district
court has accepted a guilty plea but rejects the plea agree-
ment, “[t]he only course available for the district court … is
to advise the defendant of his rights, including the right to
withdraw the guilty plea.” Ellis, 356 F.3d at 1207. It becomes
the defendant’s choice whether to stand by his plea or with-
draw it. Id. at 1208. “Nowhere does Rule 11 provide that the
district court may dictate this choice.” Id.The district court did not follow these procedures. Hav-
ing accepted Adame’s guilty plea, it decided at the July 7
No. 12-1268 15
hearing that it could not accept the plea agreement (which it
was authorized to reject), but then on its own withdrew the
plea. The court did not give Adame the choice to stand by
his guilty plea or withdraw it. Without question, Adame
wanted to persist in his plea (and even offered to abandon
his objections to the presentence report) and “proceed with
the sentencing … as the plea is written.” The district court
had no authority under Rule 11 to withdraw Adame’s plea
for him. See Ellis, 356 F.3d at 1200, 1208. It therefore abused
its discretion in doing so.
Of course, a district court may reject a guilty plea under
circumstances outlined in Rule 11(b). Santobello, 404 U.S. at
262. For example, the court may reject a plea if it determines
that it is supported by an insufficient factual basis or that the
plea was not knowing and voluntary. Cf. Hernandez-Rivas,
513 F.3d at 760–61 (district court did not abuse its discretion
in refusing to accept guilty plea after repeated attempts to
obtain a factual basis from the defendant failed and defend-
ant claimed he did not understand that his actions constitut-
ed a crime). See also United States v. Bahena-Navarro, 678 F.3d
492, 496 (7th Cir. 2012) (district court did not abuse its dis-
cretion in rejecting guilty plea where defendant declined to
waive certain trial rights). But just as the district court “can-
not arbitrarily reject a plea,” Hernandez-Rivas, 513 F.3d at 759,
surely it cannot arbitrarily withdraw a plea; it must articu-
late at least a “sound reason” for doing so. See United States
v. Rea-Beltran, 457 F.3d 695, 701–02 (7th Cir. 2006) (district
court erred in “refus[ing] to accept” defendant’s guilty plea
based on its legal misapprehension of what the law required
for a conviction); United States v. Delegal, 678 F.2d 47, 51 (7th
Cir. 1982) (holding that district court abused its discretion in
“withdrawing” a guilty plea because it thought one aspect of
16 No. 12-1268
the plea agreement, although understood by both parties,
should be contained in the written agreement and it was
not). A misunderstanding of the law is not a sound reason
for rejecting or vacating a plea: “a district court by definition
abuses its discretion when it makes an error of law.” Rea-
Beltran, 457 F.3d at 702.
We understand the district court to have withdrawn
Adame’s guilty plea because (1) it believed he had breached
the plea agreement, and (2) it found a 204-month sentence
inconsistent with the other sentences meted out to the code-
fendants—it was “too low.” Taking the latter reason first, a
district court may reject a Rule 11(c)(1)(C) plea agreement
based on its belief that the agreed-upon sentence “would be
too low to achieve the sentencing goals enumerated in 18
U.S.C. § 3553(a).” United States v. King, 506 F.3d 532, 535 (7th
Cir. 2007). But the district court’s view about an agreed-upon
sentence is not a sound reason to reject a plea. “[T]he Rules
[of Criminal Procedure] nowhere state that the guilty plea
and the plea agreement must be treated identically.” Hyde,
520 U.S. at 677. As noted, upon concluding that it would re-
ject the plea agreement, the district court’s only course was
to inform the parties, advise Adame that it would not follow
the plea agreement and give him the opportunity to with-
draw his plea, and advise him that if the plea was not with-
drawn, the court would dispose of the case less favorably to
him than contemplated in the plea—i.e., his sentence would
be greater than 204 months.
Similarly, the court lacked the authority to withdraw
Adame’s plea even if he had breached some material term of
the plea agreement. “[A] defendant's substantial breach of
an unambiguous term of a plea agreement frees the govern-
No. 12-1268 17
ment to rescind the deal.” United States v. Kelly, 337 F.3d 897,
901 (7th Cir. 2003). It does not, however, permit the district
court to rescind the plea itself and prohibit the defendant
from pleading guilty. The court apparently misapprehended
its authority to do so. Therefore, in withdrawing the plea,
the district court abused its discretion and committed legal
error.
To compound matters, the district court also erred in be-
lieving that Adame had breached the plea agreement.
“Where, as here, there is no dispute about the relevant facts,
we review de novo the interpretation of a plea agreement.”
United States v. Munoz, 718 F.3d 726, 729 (7th Cir. 2013). “Plea
agreements are contracts, and should be interpreted accord-
ing to principles of contract law. Like other contracts, plea
agreements should be enforced consistent with the intent of
the parties and the language of the agreement.” United States
v. Hernandez, 544 F.3d 743, 750–51 (7th Cir. 2008) (citations
omitted); see also United States v. Atkinson, 259 F.3d 648, 654
(7th Cir. 2001) (“[W]e review the language of the plea
agreement objectively and hold the government to the literal
terms of the plea agreement.”) (citation omitted).
Pursuant to the agreement, the parties entered into a
binding stipulation that the ”base offense level for the of-
fense charged in Count One of the Indictment is 38, pursuant
to U.S.S.G. § 2D1.1(c)(1).” The parties did not enter into any
stipulation as to the drug quantity, as the district court erro-
neously seemed to think. And the parties expressly “re-
serve[d] the right to present evidence and arguments on all
sentencing issues not specifically addressed in th[e] Plea
Agreement.” The plea agreement did not specifically ad-
dress the drug quantity personally distributed by Adame.
18 No. 12-1268
It is well known that, under the Sentencing Guidelines,
the amount of drugs involved in a drug conspiracy largely
determines a defendant’s base offense level. United States v.
Garrett, No. 13-1182, 2014 WL 2883886, at *9 (7th Cir. June 26,
2014). A base offense level of 38 corresponds to 150 kilo-
grams or more of cocaine. U.S.S.G. § 2D1.1(c)(1). For purpos-
es of calculating the quantity of drugs attributable to a de-
fendant under the Guidelines, in the case of a conspiracy it
makes no difference whether the drugs were personally de-
livered by the defendant, or whether they were delivered by
a coconspirator, as long as the other’s acts were reasonably
foreseeable to the defendant and in furtherance of the con-
spiracy. See, e.g., United States v. Davis, 682 F.3d 596, 616 (7th
Cir. 2012) (“The Guidelines instruct that a defendant in-
volved in jointly undertaken criminal activity may be held
accountable for all reasonably foreseeable acts and omissions
of others in furtherance of the jointly undertaken criminal
activity. Thus, in a drug conspiracy, each conspirator is re-
sponsible not only for drug quantities directly attributable to
him but also for amounts involved in transactions by cocon-
spirators that were reasonably foreseeable to him.”) (internal
quotation marks and citations omitted); U.S.S.G. §
1B1.3(a)(1)(B).
Adame’s objection to the assertion that he personally dis-
tributed over 150 kilograms of cocaine did not jeopardize the
calculation of the drug quantity for which he could be held
accountable. Nor was his objection inconsistent with his
agreement that his base offense level was 38, given that he
could be held accountable under § 1B1.3(a)(1)(B) for the drug
amounts delivered by others. Furthermore, Adame’s posi-
tion that he did not personally distribute 150 kilograms of
cocaine did not violate any stipulation in the written plea
No. 12-1268 19
agreement. That the government had a witness who would
testify at trial that he personally received more than 150 kil-
ograms of cocaine from Adame is beside the point. Early on
in the July 7 hearing the district court apparently recognized
how inconsequential Adame’s dispute over how much co-
caine he personally distributed was: the court said that the
defendant’s first objection to the presentence report—the ob-
jection to the amount of cocaine delivered by Adame—
“doesn’t require a ruling as I read it.” Sent. Tr. 10. But things
went off track from there, and the district court, errantly led
by the prosecutor’s urging, later concluded that Adame had
breached the plea agreement. He had not.
That brings us back to the government’s waiver argu-
ment. We readily acknowledge the general rule that “an un-
conditional plea of guilty operates as a waiver of all formal
defects in the proceedings … that occurred before the plea
was entered.” Gomez, 434 F.3d at 942. The narrow exception
to the general waiver rule has been limited to jurisdictional
issues. United States v. Phillips, 645 F.3d 859, 862 (7th Cir.
2011) (“As a general rule, a defendant who pleads guilty
waives his right to appeal all non-jurisdictional issues.”). A
jurisdictional issue refers not to subject matter jurisdiction,
but rather to “a court's statutory or constitutional authority
to hale the defendant into court.” Id. In other words, a guilty
plea does not waive a challenge to an error if, as a result of
that error, “a court has no power to enter the conviction.”
United States v. Seybold, 979 F.2d 582, 585 (7th Cir. 1992). The
Supreme Court recognized in Menna v. New York, 423 U.S. 61(1975), that a guilty plea would not necessarily extinguish a
claim under the Double Jeopardy Clause: “Where the State is
precluded by the United States Constitution from haling a
defendant into court on a charge, federal law requires that a
20 No. 12-1268
conviction on that charge be set aside even if the conviction
was entered pursuant to a counseled plea of guilty.” Id. at
62. However, the Court later narrowed this rule in United
States v. Broce, 488 U.S. 563 (1989), by holding that, in order
to circumvent a prior guilty plea on double jeopardy
grounds, a defendant must show that he faced trial or pun-
ishment from two indictments that were duplicative “on
their face.” Id. at 576. In other words, a defendant may not
“seek further proceedings at which to expand the record
with new evidence” in order to prove that he has been sub-
jected to double jeopardy. Id. at 575. Rather, the double jeop-
ardy must be apparent “at the time the [second] plea was
entered on the basis of the existing record.” Id.Adame’s case fits within this exception to the general
waiver rule. He has in essence suffered double jeopardy. The
district court withdrew the first plea through its improper
application of Rule 11, so Adame has framed the problem as
a violation of the federal rules, not the Double Jeopardy
Clause. But the district court’s error raises the same jurisdic-
tional concerns—namely, the district court’s lack of authori-
ty to hale him into court to face a subsequent indictment. See
Blackledge v. Perry, 417 U.S. 21, 31 (1974) (finding an excep-
tion to the general waiver rule—even though its “judgment
… [wa]s not based upon the Double Jeopardy Clause”—
because the case implicated similar jurisdictional concerns).
Once the district court accepted his plea the first time,
Adame was placed in jeopardy. “[J]eopardy … attaches with
acceptance of [a] guilty plea.” U.S. ex rel. Stevens v. Circuit
Court of Milwaukee Cnty., Wis., Branch VIII, 675 F.2d 946, 948
(7th Cir. 1982) (citation omitted); see Dawson v. United States,
77 F.3d 180, 182 (7th Cir. 1996). Neither the government nor
the district court had the authority to subject him to the
No. 12-1268 21
same indictment again. The second superseding indictment
presented the same charges for the same conspiracy, and
other related acts, as its predecessor. Although the factual
description of the conspiracy in Count One changed some-
what, the second superseding indictment clearly referred to
the same conspiracy. The government does not contend oth-
erwise. On its face the second superseding indictment was
an attempt by the government to redo a plea bargain process
that it felt had gone badly, for reasons that remain inexplica-
ble.
We have held that a guilty plea “forecloses any oppor-
tunity to contest any alleged antecedent constitutional dep-
rivations.” Gomez, 434 F.3d at 943. But here Adame is not
complaining of a violation “antecedent” to his second guilty
plea. The acceptance of the second guilty plea completed the
violation. It was an act the district court was utterly without
power to perform once Adame pleaded guilty to the first
superseding indictment. Adame’s claim therefore raises a
jurisdictional issue that is not waived by a guilty plea.
In addition, we are mindful of our authority to “to ensure
the proper application of [the Federal Rules of Criminal Pro-
cedure].” United States v. Vinyard, 539 F.3d 589, 595 (7th Cir.
2008) (citation and quotation marks omitted). In Vinyard we
granted the extraordinary writ of mandamus to correct a se-
rious misapplication of Rule 11 that resulted in a potential
double jeopardy problem. 5 Id. at 594 (“Vinyard never tried
5 Mandamus was necessary in Vinyard because 18 U.S.C. § 3731 bars the
United States from appealing certain orders “where the double jeopardy
clause of the United States Constitution prohibits further prosecution.”
See Vinyard, 539 F.3d at 592 (noting “a serious question whether § 3731
supports jurisdiction over an appeal”). Here, a mandamus petition is not
22 No. 12-1268
to withdraw his guilty plea; it was the court that pulled it
away from him.”). Ensuring that Rule 11 is followed is par-
ticularly important because it is the central procedural safe-
guard for a defendant who is about to waive several consti-
tutional rights. “Rule 11 is intended to ensure that a defend-
ant makes an informed and voluntary plea” as required un-
der the Due Process Clause. United States v. Mitchell, 58 F.3d
1221, 1223, 1225 (7th Cir. 1995) (discussing Rule 11’s “consti-
tutional foundation”). In this specific case, the district court
failed to adhere to Rule 11, and as a result the plea bargain
process was so confused that we cannot say with confidence
that Adame’s second plea was knowing and voluntary in all
respects. The Supreme Court has held that “a defendant is
entitled to plead anew if a United States district court ac-
cepts his guilty plea without fully adhering to the procedure
provided for in Rule 11.” McCarthy, v. United States, 394 U.S.
459, 463–64 (1969). 6 We would be unable to supervise the
application of the Federal Rules or ensure the integrity of the
plea bargaining process if such a fundamental misapplica-
tion of Rule 11 escaped review.
In sum, it would be circular to say that Adame lost the
ability to contest systematic and pervasive errors in the dis-
trict court’s handling of his plea because he pleaded guilty.
Indeed, application of the general waiver rule in this context
would have absurd consequences. It would compel a de-
necessary or appropriate because we have jurisdiction over Adame’s
appeal.
6 Congress has since made the harmless error rule applicable to Rule 11
violations. Fed. R. Crim. P. 11(h). However, as we have explained, the
failure to properly apply Rule 11 was not harmless in this instance.
No. 12-1268 23
fendant in Adame’s position to forgo his second guilty plea
and instead head to trial, all so that his original plea would
be honored. The entire point of his initial plea was to avoid a
trial and the potentially harsher punishments that go with it.
That benefit would be lost if Adame were forced to go to tri-
al—in other words, to put his liberty in jeopardy a second
time—to vindicate the plea. See Abney v. United States, 431
U.S. 651, 660 (1977) (“[T]he rights conferred on a criminal
accused by the Double Jeopardy Clause would be signifi-
cantly undermined if appellate review of double jeopardy
claims were postponed until after conviction and sen-
tence.”).
The risk of prosecutorial manipulation is also a concern.
In Blackledge, 417 U.S. at 28, the Supreme Court held that a
guilty plea did not waive the petitioner’s due process chal-
lenge because “[a] person convicted of an offense is entitled
to pursue his statutory right … without apprehension that
the State will retaliate” by improperly haling him back into
court. Likewise, the government may sometimes be tempted
to scrap a judicially accepted plea and issue a new indict-
ment to add factual support or correct procedural infirmi-
ties. But it cannot do so, any more than it can retry an al-
ready-convicted defendant in order to obtain a special ver-
dict rather than a general one. In this case the government
obtained a guilty plea, pointed to a trivial “breach” to get the
plea withdrawn, and then re-indicted Adame based on a
slightly modified description of the original conspiracy
count. But had he gone to trial to dispute the withdrawal of
his plea, he would have risked losing his credit for ac-
ceptance of responsibility as well. In a sense, the government
profited from its own breach of the plea agreement (in fail-
ing to recommend the agreed 204-month sentence), and
24 No. 12-1268
Adame could object only by risking the plea itself. Rule 11 is
the defendant’s chief bulwark against prosecutorial abuse,
and the Rule was not followed in this case. The district court
clearly lacked the authority to put Adame in such an unten-
able situation, so his claim is jurisdictional.
There is one final obstacle to Adame’s appeal. We have
held that even “double jeopardy rights may be waived by
failing to preserve the issue for appeal.” Gomez, 434 F.3d at
943. But Adame plainly filed a motion to reinstate his earlier
plea, and therefore sufficiently raised the issue before the
district court. We are particularly reluctant to hold that
Adame failed to preserve this issue for review because the
district court did not properly articulate the extent of his ap-
peal waiver. The court did not clearly inform Adame that a
guilty plea would deprive him of his ability to appeal the
court’s revocation of his initial plea. See United States v. Wool-
ley, 123 F.3d 627, 632 (7th Cir. 1997) (“For an appeal waiver
to be valid, it must be express and unambiguous, and the
record must clearly demonstrate that it was made knowingly
and voluntarily.”) (citations and internal quotation marks
omitted). Adame did all he could to raise the issue given the
complicated posture of this case. 7 A finding of waiver would
be inappropriate here in light of this strange, and hopefully
unique, procedural history.
7Adame perhaps could have filed a mandamus petition requesting that
we order the district court to reinstate his initial plea agreement, but that
petition would surely have failed. Adame had adequate means to obtain
his desired relief by appealing to this court. See Cheney v. U.S. District
Court, 542 U.S. 367, 380 (2004). The possibility that he did not adequately
preserve his objections for appeal does not alter the availability of that
option. An objection followed by a timely appeal, not mandamus, is the
proper means for resolving disputes over the plea bargain process.
No. 12-1268 25
Our holding is an exceedingly narrow one, and pertains
only to cases in which a defendant pleads guilty after the
district court has already accepted a guilty plea to charges
that, on the face of the indictment or other charging docu-
ment, are identical to those the defendant pleads to in the
later proceeding. This case fits well within the exception to
the general waiver rule already recognized in Menna and
Blackledge, and a guilty plea will still act to bar typical objec-
tions against the district court’s handling of plea agreements
and related issues.
We reach past Adame’s second guilty plea and reverse
the district court’s errors in vacating the plea agreement for
his supposed breach. Adame is entitled to the benefit of his
bargain. On remand, the district court should advise the par-
ties whether it accepts or rejects the original plea agreement
and follow the procedures laid out in Rule 11. Because
Adame did not breach the plea agreement, the United States
must keep its promise not to file an information concerning
his past criminal history pursuant to 21 U.S.C. § 851. In order
to provide this discrete issue a fresh look, freed from the
complicated procedural history of this case, we believe a re-
assignment to another district court judge is appropriate.
Likewise, “[w]e expect that a different prosecutor from the
U.S. Attorney's office will appear before that judge” and
avoid making any unsubstantiated claims that Adame has
breached his agreement. United States v. Diaz-Jimenez, 622
F.3d 692, 697 (7th Cir. 2010).
26 No. 12-1268
CONCLUSION
For the foregoing reasons, we VACATE Adame’s convic-
tions and REMAND with instructions to allow Adame to
maintain his guilty plea and be sentenced under the terms of
the parties’ written plea agreement executed on January 3,
2011. Circuit Rule 36 shall apply on remand.