In the

United States Court of Appeals

For the Seventh Circuit ____________________ 

No. 21-1326 

UNITED STATES OF AMERICA, 

Plaintiff-Appellee, 

v.

THOMAS L. GOLIDAY, 

Defendant-Appellant. 

____________________ 

Appeal from the United States District Court for the

Southern District of Indiana, Indianapolis Division.

No. 1:18-CR-00331 — James P. Hanlon, Judge. 

____________________ 

ARGUED APRIL 27, 2022 — DECIDED JULY 15, 2022 

____________________ 

Before SYKES, Chief Judge, and BRENNAN and SCUDDER, Circuit Judges. 

SCUDDER, Circuit Judge. Thomas Goliday sold drugs in Indianapolis, found himself facing federal charges, and chose to 

plead guilty to three counts of possession and one count of 

conspiracy to distribute heroin. Confusion as to this latter 

charge emerged during the plea proceeding, however, with 

Goliday making statements suggesting he did not understand 

how a conspiracy offense differed from just buying and 
2 No. 21-1326 

selling drugs. The facts acknowledged during the plea offered 

no clarity on the point either and, even more, the district court 

did not follow up to resolve the confusion. Some step should 

have been taken to ensure not only that Goliday understood 

the nature of the charged conspiracy offense, but also that 

there was a factual basis for the guilty plea. On the record before us, then, we cannot avoid the conclusion that it was plain 

error for the district court to accept the plea.

I 

In late September 2018 a team of officers from both the Indianapolis Metropolitan Police Department and the federal 

Drug Enforcement Agency executed a search warrant at 

Thomas Goliday’s home in Indianapolis, recovering assorted 

drugs and a loaded handgun. Goliday, who arrived home 

during the search, waived his Miranda rights and agreed to 

speak to the officers. He admitted that the drugs and gun 

found in the home were his. Apparently seeking to cooperate 

with the investigation in hopes of obtaining more lenient 

treatment from prosecutors, Goliday told the officers that he 

had bought two ounces of heroin every week for the last year 

from the same supplier. He explained that he would then resell the heroin in smaller amounts to users.

Federal narcotics charges followed. A superseding indictment charged Goliday with three counts of possession with 

intent to distribute drugs—one count each for the fentanyl, 

methamphetamine, and crack cocaine recovered from his 

home. See 21 U.S.C. § 841(a)(1). Goliday’s attempted cooperation did not pan out—indeed, from his perspective, it backfired. In the government’s view, his statements to police regarding his heroin purchases supplied the basis for an additional charge. Adding together the weekly two-ounce 
No. 21-1326 3

purchases from his supplier, the indictment charged Goliday 

with conspiring to distribute more than 1,000 grams of heroin. 

See id. §§ 841(a)(1), 846. Alongside these charges, the government filed an information under 21 U.S.C. § 851 notifying Goliday that, based on a prior felony drug conviction, he faced an 

enhanced sentence if convicted here.

Goliday decided to plead guilty to all charges. Without the 

conspiracy charge, he would have faced a statutory minimum 

sentence of 10 years and a maximum of life. But the conspiracy charge, as enhanced by Goliday’s prior conviction, carried 

a statutory minimum of 15 years, or 180 months. See id.

§ 841(b). Accordingly, while the federal Sentencing Guidelines recommended a sentence between 168 and 210 months, 

the addition of the conspiracy charge narrowed that range to 

180 to 210 months. 

Goliday’s plea hearing got off to a sound start. The district 

court confirmed he was feeling well, wanted to plead guilty, 

and understood that by doing so he was giving up important 

constitutional rights. The district court then set about fulfilling its obligations under Federal Rule of Criminal Procedure 11 to describe the charges to which Goliday was pleading guilty and to ensure there was an adequate factual basis 

for concluding he committed each offense.

The district court began with the § 846 charge for conspiracy to distribute heroin. The court explained that, to secure a 

conviction at trial, the government would have to prove that 

(1) “the alleged [heroin] conspiracy ... existed,” that it (2) “involved 1,000 grams or more” of heroin, and that (3) Goliday 

“knowingly and intentionally became a member of that conspiracy.” Goliday said he understood these elements.
4 No. 21-1326 

The government then read into the record what it viewed 

as the factual basis for Goliday’s plea to the conspiracy 

charge: “Through investigation, officers learned that Goliday 

had been receiving 2 ounces of heroin a week for a year from 

a coconspirator, [totaling] in excess of 1,000 grams of heroin, 

which heroin he then resold to others in exchange for financial 

remuneration.”

When the district court asked Goliday if these facts were 

true and accurate, the following exchange occurred:

GOLIDAY: Not the 1,000 grams.

COURT: Not the what, I’m sorry?

GOLIDAY: The 1,000 grams.

COURT: Well, let me ask you this, do you 

agree that the government would be able to 

prove those facts that [it] just read into the record at a trial beyond a reasonable doubt if this 

case were to go to trial?

GOLIDAY: I don’t see how. There was a statement that I made to the authorities to help them 

with my supplier to help him get convicted. The 

statement that I made to the police was just to 

tell them where I was getting my drugs from 

and that boosted that quantity up like that. 

I didn’t have that much drugs. I only had 

80 grams of dope in my house at that time. The 

1,000 grams, I made a statement to the agents 

telling them that they can go bust this guy and 

get the drugs from him and they asked me how 

much I was getting from this guy and I told 

them and they turned around and used that to 
No. 21-1326 5

boost my quantity up and put me in a conspiracy because when I first got locked up it wasn’t 

a conspiracy at all.

COURT: Okay. Well, the question, then, is 

that there is no allegation that you had 

1,000 grams or more of a mixture or substance 

that contained a detectable amount of heroin. It 

alleges that there was a conspiracy to possess 

with intent to distribute and to distribute heroin 

and that the conspiracy involved 1,000 grams or 

more.

GOLIDAY: Yes, sir.

COURT: And is that true?

GOLIDAY: Yes, sir. 

COURT: Okay. And the facts otherwise set 

forth in the factual basis [the government] read 

are accurate and true? 

GOLIDAY: Yes, sir.

On the basis of this exchange, the district court found a 

sufficient factual basis for Goliday’s guilty plea to the conspiracy charge. So, too, did the district court find sufficient factual 

support for Goliday’s plea to the three § 841(a)(1) substantive 

drug possession charges. The district court then sentenced 

Goliday to four concurrent terms of imprisonment of 180 

months or 15 years—the statutory minimum sentence for the 

conspiracy charge.

Goliday now appeals, arguing that the district court 

should not have accepted his plea to the conspiracy charge. 

The district court, Goliday contends, committed a twofold 
6 No. 21-1326 

error by not ensuring he understood the nature of the conspiracy charge and not confirming the existence of facts sufficient 

to demonstrate a conspiracy with his heroin supplier.

II

Rule 11(b) of the Federal Rules of Criminal Procedure requires district courts to adhere to a series of obligations before 

accepting a criminal defendant’s guilty plea. Two of those requirements are relevant here. To begin with, “the court must 

inform the defendant of, and determine that the defendant 

understands,” the “nature of each charge” to which he wishes 

to plead guilty. Fed. R. Crim. P. 11(b)(1)(G). Doing so is essential to ensure compliance with the due process requirement 

that a defendant’s guilty plea be “truly voluntary.” McCarthy 

v. United States, 394 U.S. 459, 465 (1969). 

But that is not the end of the matter. Beyond ensuring that 

a defendant understands the charges against him, a district 

court may not enter judgment on a guilty plea until it has 

made an independent judicial determination “that there is a 

factual basis for the plea.” Fed. R. Crim. P. 11(b)(3). The failure to substantially comply with either of these requirements 

may be grounds for vacating the plea, so long as the error is 

not harmless. See Fed. R. Crim. P. 11(h); United States v. 

Blalock, 321 F.3d 686, 688–89 (7th Cir. 2003) (requiring only 

substantial compliance with, not literal adherence to, the commands of Rule 11). 

Still, because Goliday did not object to the factual basis or 

move to withdraw his guilty plea in the district court, we review the court’s compliance with Rule 11 in accepting his plea 

only for plain error. See United States v. Vonn, 535 U.S. 55, 59 

(2002); Fed. R. Crim. P. 52(b). To win relief under this exacting 
No. 21-1326 7

standard, Goliday must show that the district court committed an error that was “clear or obvious,” that prejudiced his 

substantial rights, and that “seriously affected the fairness, integrity, or public reputation of the judicial proceedings.” 

United States v. Triggs, 963 F.3d 710, 714 (7th Cir. 2020). 

Goliday clears this high bar. We have reviewed the plea 

colloquy several times, and each time we come away with the 

same impression—confusion. Even under plain error review,

we cannot say that Goliday understood the nature of the conspiracy charge against him or that the district court had an 

adequate factual basis for accepting his plea. 

A 

Start with the district court’s threshold obligation to ensure that Goliday understood the nature of the charges 

against him. See Fed. R. Crim. P. 11(b)(1)(G). Because a guilty 

plea is an admission to each element of a criminal charge, due 

process requires a defendant to understand “the elements of 

the crime” with which he is charged. United States v. Schaul, 

962 F.3d 917, 922 (7th Cir. 2020). Accordingly, “[w]hen there 

is general confusion over the elements of the crime with 

which a defendant is charged, the resulting guilty plea cannot 

stand.” Id.

Defendants may be particularly susceptible to misunderstanding the elements of a drug conspiracy under § 846, 

which we have called “a complex charge not always or easily 

understood by a layperson.” United States v. Neal, 907 F.3d 

511, 514 (7th Cir. 2018). This is so in large part because of a 

fine but crucial distinction regarding the core element of a 

criminal conspiracy—agreement. Time and again we have 

underscored that proof of an ordinary buyer-seller 
8 No. 21-1326 

relationship alone is insufficient to support a conviction under § 846. See id. at 515 (citing United States v. Long, 748 F.3d 

322, 325 (7th Cir. 2014)). As the Supreme Court has explained, 

“[t]he essence of conspiracy is the combination of minds in an 

unlawful purpose.” Smith v. United States, 568 U.S. 106, 110 

(2013) (cleaned up). In that light, “ordinary drug transactions 

do not entail or reflect conspiracy, for the buyer’s only purpose is to buy and the seller’s only purpose is to sell: the buyer 

and seller lack a shared criminal goal.” Neal, 907 F.3d at 515 

(emphasis in original).

This explains why our cases have emphasized that a § 846 

conviction requires “evidence of an agreement to commit a 

crime other than the crime that consists of the sale [of drugs] 

itself.” United States v. Johnson, 592 F.3d 749, 754 (7th Cir. 2010) 

(cleaned up); United States v. Vizcarra-Millan, 15 F.4th 473, 506 

(7th Cir. 2021) (explaining that the government must prove 

“that the defendant knowingly agreed, perhaps implicitly, 

with someone else to distribute”—not just to purchase—

“drugs”); United States v. Duran, 407 F.3d 828, 835 (7th 

Cir. 2005) (setting out two elements of a § 846 conviction: 

“(1) two or more people agreed to commit an unlawful act, 

and (2) the defendant knowingly and intentionally joined 

in the agreement”). Our pattern jury instructions follow 

suit. See The William J. Bauer Pattern Criminal Jury Instructions 

of the Seventh Circuit § 5.10(A) (2020 ed.) (requiring the government to “prove that the buyer and seller had the joint criminal objective of further distributing [controlled substances] to 

others”).

Against this backdrop, it is clear that a defendant charged 

with conspiracy under § 846 cannot be found to understand 

the “nature of [the] charge” if he does not evince some 
No. 21-1326 9

acknowledgement that conviction requires proof of a joint 

criminal purpose beyond a mere buyer-seller relationship. 

Fed. R. Crim. P. 11(b)(1)(G).

But where Rule 11 demands clarity, our review of the plea 

colloquy reveals “general confusion.” Schaul, 962 F.3d at 922. 

At the outset of the hearing, the district court told Goliday that 

to prove the conspiracy charge, the government would have 

to show: 

first that the alleged conspiracy with intent to 

distribute and to distribute controlled substances existed; second, that [he] knowingly and 

intentionally became a member of that conspiracy; and last, that the conspiracy involved 1,000 

grams or more of a mixture or substance containing a detectable amount of heroin.

The district court’s explanation is accurate as far as it goes, 

but on this record it did not go far enough. According to the 

district court, the first element of a § 846 conspiracy is that the 

“conspiracy ... existed.” That might have sufficed if, in the totality of the circumstances, other portions of the plea colloquy 

gave us comfort that Goliday understood the charge against 

him. But we know from what Goliday later said that he harbored significant confusion about perhaps the key element of 

the conspiracy charge: “an agreement [between Goliday and 

his supplier] to commit a crime other than the crime that consists of the sale itself.” Johnson, 592 F.3d at 754 (cleaned up). 

After the government read its proffered factual basis into 

the record, Goliday spoke up. He told the district court that 

he did not understand how he could be liable for the full 

1,000 grams involved in the alleged conspiracy, maintaining 
10 No. 21-1326 

that he only had “80 grams ... in [his] house” and that he had 

only mentioned the 1,000-gram amount in a statement to investigators “to help them [convict his] supplier”—so they 

could “go bust this guy and get the drugs from him.” 

Goliday’s statements to this point reflect a two-fold misunderstanding. First, he did not appreciate that he faced 

charges for entering into a more wide-reaching partnership 

with his supplier beyond an agreement to buy particular 

quantities of heroin. Second, he did not understand the consequences of conceding that point—that he would be held legally responsible for all drug amounts traceable to that illegal 

agreement, not just those quantities he possessed at the time 

of his arrest. 

The district court seemed to sense Goliday’s confusion. Indeed, the court responded by explaining that the government’s allegation was not that he personally possessed or sold 

1,000 grams, but rather only that “there was a conspiracy” to

distribute that amount of heroin. But while the court was right 

to pause on this point, in our view its explanation did not go 

far enough. Clarifying that the heightened drug quantity was 

attributable to a conspiracy rather than to simple possession 

was surely helpful. But we are not assured that these statements adequately informed Goliday of the government’s obligation to prove the agreement at the heart of the conspiracy. 

Without the court taking that additional step, the record remained as murky as it was before the attempted clarification

on the key question before us: whether Goliday understood 

the nature of the charges against him.

Rule 11 required more in these circumstances. On the totality of the facts before us, we cannot conclude that Goliday 

understood “the nature of [the conspiracy] charge” to which 
No. 21-1326 11

he was attempting to plead guilty. Fed. R. Crim. 

P. 11(b)(1)(G). Faced with Goliday’s evident confusion on this 

crucial point, Rule 11 required the district court to tap the 

brake pedal and slow things down a touch to ensure that Goliday knew what he was accepting responsibility for. And to 

our eye, not doing so reflected “clear [and] obvious” error. 

Triggs, 963 F.3d at 714. Proceeding a shade slower to develop 

the requisite factual record is a small price to pay for avoiding 

a plea that is not “truly voluntary.” McCarthy, 394 U.S. at 465.

B 

We see a similar error with respect to the district court’s 

Rule 11(b)(3) obligation to ensure a sufficient factual basis for 

accepting Goliday’s guilty plea on the conspiracy count. Recall that a conspiracy conviction requires proof of a criminal 

agreement beyond the confines of an ordinary buyer-seller relationship. See Neal, 907 F.3d at 515. To be sure, the government may show the requisite agreement with circumstantial 

evidence, such as evidence of “sales on credit or consignment” or other circumstances suggesting a “unity of enterprise” between buyer and seller. Id. at 515–16 (quoting Johnson, 592 F.3d at 755–56). But purchases alone will not suffice.

Yet purchases alone are all the government represented it 

has in this case: the government’s proffered factual basis asserted that Goliday “had been receiving two ounces of heroin 

a week for a year from a coconspirator,” which he then “resold to others in exchange for financial remuneration.” The 

government contends this evidence of regular purchases of 

large quantities of heroin suffices to create a factual basis for 

Goliday’s conspiracy plea.
12 No. 21-1326 

We have rejected the argument before and do so again today. A prosecution based “only on evidence that a buyer and 

seller traded in large quantities of drugs, used standardized 

transactions, and had a prolonged relationship” leaves the 

jury to “choose between two equally plausible inferences”—a 

conspiracy and an ordinary buyer-seller relationship are 

equally likely. Johnson, 592 F.3d at 755. With the evidence thus 

“essentially in equipoise,” we have said, “the jury must acquit” in the absence of “some other evidence of a conspiratorial agreement to tip the scales.” Id.; see also United States v. 

Colon, 549 F.3d 565, 569 (7th Cir. 2008) (rejecting the argument 

that any “wholesale customer of a conspiracy is a co-conspirator per se”). We see no reason these principles fail to apply in 

the context of evaluating a factual basis for a plea under 

Rule 11. 

The government points to one additional piece of evidence 

that it says tips the scales in favor of conspiracy: Goliday’s 

failure to object to the government’s use of the word “coconspirator”—both in the presentence investigation report and in 

the proffered factual basis—to refer to his heroin supplier. As 

the government sees things, that failure amounted to an admission by Goliday that he and his supplier were in fact engaged in a conspiracy.

That assertion brings us back to the district court’s first 

shortcoming—not assuring Goliday understood the elements 

of a conspiracy. If Goliday operated on the mistaken understanding that an ordinary buyer-seller relationship sufficed to 

show a drug conspiracy—and nothing in the record indicates 

he was under any different impression—his acquiescence in 

the government’s use of the term “coconspirator” to refer to 

his supplier is not surprising. Nor does it change the fact that 
No. 21-1326 13

the existence of a coconspirator (and, thus, of a conspiracy) is 

a legal conclusion which the government would have had 

to prove beyond a reasonable doubt at trial. Criminal defendants, in short, “may not stipulate to legal conclusions in 

plea agreements.” In re Sealed Case, 936 F.3d 582, 590 (D.C. 

Cir. 2019). 

On the record before us, we see no way to avoid the conclusion that the district court plainly erred by accepting Goliday’s plea without an adequate factual basis. 

C 

On plain error review, the mere existence of these Rule 11 

errors does not entitle Goliday to relief. He must also convince 

us that these errors affected both his substantial rights and 

“the fairness, integrity, or public reputation of the judicial 

proceedings.” Triggs, 963 F.3d at 714. 

To demonstrate that the Rule 11 errors affected his substantial rights, Goliday must show a reasonable probability 

that, but for the errors, he would not have pled guilty to the 

conspiracy charge. See United States v. Sura, 511 F.3d 654, 658 

(7th Cir. 2007) (citing United States v. Dominguez Benitez, 542 

U.S. 74, 76 (2004)). We look to the entire record to determine 

whether he made this showing, see Dominguez Benitez, 542 

U.S. at 83, and conclude that he did so. 

Had Goliday understood the elements of conspiracy, he 

would have known that the government would have to prove 

beyond a reasonable doubt at trial that he agreed to join a 

criminal enterprise involving more than his individual drug 

purchases. Yet we see no evidence from the proffered factual 

basis for the plea indicating how the government could meet 

this burden.
14 No. 21-1326 

Given this evidentiary void, Goliday’s confusion about his 

liability for the 1,000 grams should have signaled to the district court that he did not understand he was part of a 

joint criminal enterprise with his supplier. It follows that 

there exists a reasonable probability that he would have assessed his strategic position at trial differently had he understood the government’s evidentiary burden and its apparent 

lack of evidence on the key element of agreement. See id. at 

85; see also Triggs, 963 F.3d at 717 (finding a reasonable probability that the defendant would not have pled guilty had he 

known that to convict him of unlawful firearm possession, the 

government had to prove he knew he belonged to the relevant 

category of persons barred from possession). This is especially so because the conspiracy charge increased Goliday’s 

sentencing exposure, including by requiring the imposition of 

a mandatory minimum 15-year sentence and increasing the 

floor of his advisory Guidelines range from 168 to 180 months.

That leaves the question whether the error is so serious as 

to impugn the “fairness, integrity, or public reputation of the 

judicial proceedings” and justify the exercise of “our discretionary authority to correct an unpreserved error.” Triggs, 963 

F.3d at 717. We believe the answer is yes in the totality of what 

is before us here. The district court did not ensure that Goliday had “real notice of the true nature of the charges against 

him,” which the Supreme Court has called “the first and most 

universally recognized requirement of due process.” Bousley 

v. United States, 523 U.S. 614, 618 (1998). And its failure to ensure an adequate basis for the plea means the court may have 

allowed Goliday to plead guilty to an offense of which he is 

actually innocent. See United States v. Olano, 507 U.S. 725, 736 

(1993). Neither error can stand.
No. 21-1326 15

* * * 

For these reasons, we VACATE the conspiracy conviction 

under 21 U.S.C. § 846 and REMAND for further proceedings 

on that charge. Likewise, because the mandatory minimum 

sentence for the § 846 conviction may well have increased 

Goliday’s sentence on the other three counts of conviction, we 

VACATE those sentences and REMAND for plenary resentencing.