United States of America v. Thomas L. Goliday

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 21-1326
U NITED S TATES OF A MERICA,
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.
____________________
A RGUED A PRIL 27, 2022 — DECIDED J ULY 15, 2022
____________________
Before S YKES , Chief Judge, and BRENNAN and S CUDDER , Cir-
cuit Judges.
SCUDDER , Circuit Judge. Thomas Goliday sold drugs in In-
dianapolis, 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

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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 be-
fore 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 In-
dianapolis 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 re-
sell the heroin in smaller amounts to users.
Federal narcotics charges followed. A superseding indict-
ment 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 cooper-
ation did not pan out—indeed, from his perspective, it back-
fired. In the government’s view, his statements to police re-
garding his heroin purchases supplied the basis for an addi-
tional charge. Adding together the weekly two-ounce

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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 govern-
ment filed an information under 21 U.S.C. § 851 notifying Gol-
iday 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 conspir-
acy 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 Guide-
lines 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 ful-
filling its obligations under Federal Rule of Criminal Proce-
dure 11 to describe the charges to which Goliday was plead-
ing 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 conspir-
acy 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) “in-
volved 1,000 grams or more” of heroin, and that (3) Goliday
“knowingly and intentionally became a member of that con-
spiracy.” Goliday said he understood these elements.

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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 rec-
ord at a trial beyond a reasonable doubt if this
case were to go to trial?
GOLIDAY: I don’t see how. There was a state-
ment 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

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No. 21-1326 5
boost my quantity up and put me in a conspir-
acy 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 conspir-
acy 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

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6 No. 21-1326
error by not ensuring he understood the nature of the conspir-
acy 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 re-
quires district courts to adhere to a series of obligations before
accepting a criminal defendant’s guilty plea. Two of those re-
quirements 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 essen-
tial 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 fail-
ure 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 com-
mands 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 re-
view 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

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No. 21-1326 7
standard, Goliday must show that the district court commit-
ted an error that was “clear or obvious,” that prejudiced his
substantial rights, and that “seriously affected the fairness, in-
tegrity, 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 con-
spiracy 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 en-
sure 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 misunder-
standing 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

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8 No. 21-1326
relationship alone is insufficient to support a conviction un-
der § 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 pur-
pose 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 gov-
ernment to “prove that the buyer and seller had the joint crim-
inal 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

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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 sub-
stances existed; second, that [he] knowingly and
intentionally became a member of that conspir-
acy; and last, that the conspiracy involved 1,000
grams or more of a mixture or substance con-
taining 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 to-
tality 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 har-
bored 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 con-
sists 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

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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 in-
vestigators “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 mis-
understanding. 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 con-
sequences of conceding that point—that he would be held le-
gally 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. In-
deed, the court responded by explaining that the govern-
ment’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 state-
ments adequately informed Goliday of the government’s ob-
ligation to prove the agreement at the heart of the conspiracy.
Without the court taking that additional step, the record re-
mained 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 to-
tality of the facts before us, we cannot conclude that Goliday
understood “the nature of [the conspiracy] charge” to which

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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 Gol-
iday 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. Re-
call that a conspiracy conviction requires proof of a criminal
agreement beyond the confines of an ordinary buyer-seller re-
lationship. See Neal, 907 F.3d at 515. To be sure, the govern-
ment may show the requisite agreement with circumstantial
evidence, such as evidence of “sales on credit or consign-
ment” or other circumstances suggesting a “unity of enter-
prise” between buyer and seller. Id. at 515–16 (quoting John-
son, 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 as-
serted that Goliday “had been receiving two ounces of heroin
a week for a year from a coconspirator,” which he then “re-
sold 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.

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12 No. 21-1326
We have rejected the argument before and do so again to-
day. 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 ac-
quit” in the absence of “some other evidence of a conspirato-
rial 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-conspira-
tor 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 “cocon-
spirator”—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 ad-
mission by Goliday that he and his supplier were in fact en-
gaged 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 under-
standing 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

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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 defend-
ants, 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 con-
clusion that the district court plainly erred by accepting Goli-
day’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 sub-
stantial 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.

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14 No. 21-1326
Given this evidentiary void, Goliday’s confusion about his
liability for the 1,000 grams should have signaled to the dis-
trict 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 as-
sessed his strategic position at trial differently had he under-
stood 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 prob-
ability 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 espe-
cially 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 discre-
tionary 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 Goli-
day 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 en-
sure 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.

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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 resen-
tencing.

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