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 AdameHernandez (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others but because his appeal arises from substantially different circumstances that are unique to him, we have withdrawn the consolidation of his appeal to address it separately in this opinion.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 cocaine distribution and illegal reentry of a previously deported 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, written 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 conspiracy charged in Count One of the superseding indictment. 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 release 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 sentencing issues not specifically addressed in this Plea Agreement.” Counts Two and Three of the superseding indictment, charging cocaine distribution and illegal re-entry, respectively, 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 discussed 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 understand that while the Court is not a party to this 

agreement, in the event the Court determines the sentence 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 established 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 sentence, and that the probation office had to prepare a presentence investigation report, which the court would use “along 

with [the] plea agreement that has the specific sentence bargained 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 objections to the report: he denied that he personally delivered 

over 150 kilograms of cocaine, and he objected to a fact underlying an adjustment for his aggravated role in the offense.

About six months after the guilty plea, on July 7, 2011, 

Adame returned to the district court for sentencing. The record does not disclose that he had any prior notice that anything 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 stipulated to in the plea agreement and asserted that this constituted grounds to find a breach of the plea agreement. The 
No. 12-1268 5

prosecutor also asserted that the trial evidence would establish 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 offense level that involved a drug quantity calculation, defense 

counsel responded in the affirmative. 

The district court stated that if the defendant “[is] backing 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 because I meted out those sentences. For him to have 

been in the leadership role that he was in in this conspiracy and a supplier of such a huge amount of cocaine, 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 meted 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 distribution 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 subsequent redistribution of crack cocaine through the Indianapolis conspirators. Nonetheless, the government does not contend 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 Detective 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 indictment. It is important to note that Adame’s waiver does not 

contain a plea to the charges in the second superseding indictment, despite the fact that the form of such waivers posted 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 opportunity to withdraw the plea; and that if the plea is not withdrawn, the Court may dispose of the case less favorably toward me than the plea contemplated.” And rather than indicating that he desired to enter a guilty plea to the new, second 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 defendants 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 indeed, 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 indicated 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 intended 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 rejected. Id. at 8. But even with that reminder, the confusion continued 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 appellate 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 Government’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 question, it is hard for us to discern what he may have understood 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, despite differences in the wording of the conspiracy counts between 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 recommended a two-level enhancement for Adame’s role in the 

offense, the report following the October 2011 plea recommended 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 subsequently 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 reinstatement of his initial plea agreement along with the joint recommendation 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 vacating 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 government 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 challenge 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 information pursuant to its plea agreement with Adame. Because we now 

hold the government to the terms of that bargain, the filing of that information 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 contest 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 withdraw 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 waiver 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 superseding 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 accepted 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 hearing 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] agreement,” Adame answered, “Yes.” Sent. Tr. 9. Adame points to no authority 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 deferred. ... [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 governed 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 withdraw 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, according 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 contemplates that the district court’s rejection of a plea agreement allows the defendant, not the court, to make the next decision 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 agreement, “[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 withdraw 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. Having 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 defendant claimed he did not understand that his actions constituted a crime). See also United States v. Bahena-Navarro, 678 F.3d 

492, 496 (7th Cir. 2012) (district court did not abuse its discretion in rejecting guilty plea where defendant declined to 

waive certain trial rights). But just as the district court “cannot arbitrarily reject a plea,” Hernandez-Rivas, 513 F.3d at 759, 

surely it cannot arbitrarily withdraw a plea; it must articulate 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.” ReaBeltran, 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 codefendants—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 reject 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 withdraw his plea, and advise him that if the plea was not withdrawn, 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 believing 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 according 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 offense 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 erroneously seemed to think. And the parties expressly “reserve[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 address 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 kilograms or more of cocaine. U.S.S.G. § 2D1.1(c)(1). For purposes of calculating the quantity of drugs attributable to a defendant under the Guidelines, in the case of a conspiracy it 

makes no difference whether the drugs were personally delivered 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 conspiracy. See, e.g., United States v. Davis, 682 F.3d 596, 616 (7th 

Cir. 2012) (“The Guidelines instruct that a defendant involved 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 responsible not only for drug quantities directly attributable to 

him but also for amounts involved in transactions by coconspirators 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 distributed 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 position 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 kilograms 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 cocaine he personally distributed was: the court said that the 

defendant’s first objection to the presentence report—the objection 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 argument. We readily acknowledge the general rule that “an unconditional 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 punishment 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 subjected to double jeopardy. Id. at 575. Rather, the double jeopardy 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 jurisdictional concerns—namely, the district court’s lack of authority to hale him into court to face a subsequent indictment. See 

Blackledge v. Perry, 417 U.S. 21, 31 (1974) (finding an exception 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 somewhat, the second superseding indictment clearly referred to 

the same conspiracy. The government does not contend otherwise. 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 inexplicable.

We have held that a guilty plea “forecloses any opportunity to contest any alleged antecedent constitutional deprivations.” 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 Procedure].” 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 serious 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 particularly important because it is the central procedural safeguard for a defendant who is about to waive several constitutional rights. “Rule 11 is intended to ensure that a defendant makes an informed and voluntary plea” as required under the Due Process Clause. United States v. Mitchell, 58 F.3d 

1221, 1223, 1225 (7th Cir. 1995) (discussing Rule 11’s “constitutional 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 accepts 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 misapplication 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 district 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 trial—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 significantly undermined if appellate review of double jeopardy 

claims were postponed until after conviction and sentence.”). 

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 challenge 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 indictment to add factual support or correct procedural infirmities. But it cannot do so, any more than it can retry an already-convicted defendant in order to obtain a special verdict 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 acceptance of responsibility as well. In a sense, the government 

profited from its own breach of the plea agreement (in failing 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 untenable 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 appeal 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. Woolley, 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.

 7 Adame 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 document, 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 objections 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 parties 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 reassignment 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 convictions 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.