NOT RECOMMENDED FOR PUBLICATION

File Name: 21a0482n.06

Case Nos. 20-3019/3223/3393

UNITED STATES COURT OF APPEALS

FOR THE SIXTH CIRCUIT

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

JOSEPH P. GRAY, JR., LARRY JACKSON, and

SHONDELL MACK,

Defendants-Appellants.

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ON APPEAL FROM THE 

UNITED STATES DISTRICT 

COURT FOR THE NORTHERN 

DISTRICT OF OHIO

OPINION 

Before: SILER, KETHLEDGE, and BUSH, Circuit Judges.

JOHN K. BUSH, Circuit Judge. An organization called the “Grovewood Boys” trafficked

heroin, often mixed with fentanyl or fentanyl analogues, and crack cocaine in east Cleveland, Ohio. 

Three group members, who pleaded guilty, bring this appeal. Two, Joseph Gray, Jr. and Shondell 

Mack, challenge their sentences. The third, Larry Jackson, argues that his guilty plea is invalid. 

None of these arguments has merit, so we affirm. 

I.

We need only summarize this sprawling conspiracy to resolve these appeals. In total, 

twenty-two defendants were indicted for their role in the organization; all pleaded guilty. 

Law enforcement began investigating the Grovewood Boys in January 2018. Wiretaps 

revealed that the group obtained drugs in bulk quantities and divided them for re-sale among the

members. Dealers either sold to their own customer bases or communicated with customers via a 

single, shared phone line open to any customer. Known as the “customer phone,” this device was 
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passed among the various dealers. When a physical phone became unusable, the customer phone’s 

number and data was simply transferred to a new device. As a result, potential customers could 

reach the Grovewood Boys nearly twenty-four hours a day. 

The Grovewood Boys said they dealt heroin and cocaine. But their labels were inaccurate: 

the “heroin” was more often fentanyl, fentanyl analogues, or heroin laced with fentanyl or its 

analogues; the “cocaine” was usually crack cocaine. Slang was commonplace in the transactions: 

the heroin or fentanyl was called “boy,” while the crack cocaine was called “girl.” The dealers 

operated primarily on the east side of Cleveland and in nearby suburbs. 

The defendants here were members of the Grovewood Boys. Their roles in the conspiracy 

varied, and different parts of the proceedings below are relevant to each appeal, so we address each 

defendant separately. 

Joseph P. Gray. When a dealer needed access to the customer phone, he “had to go through 

Joseph Gray.” Gray monitored dealers’ supply levels, obtained the bulk drugs, and coordinated 

the sales to customers. Put simply, he led the Grovewood Boys. A federal grand jury returned a 

twenty-two count indictment against Gray, which included one charge for conspiracy to possess 

with intent to distribute controlled substances, two charges for distribution, eight charges for 

possession with intent to distribute, two firearms-related charges, and nine counts for using a 

communication facility in furtherance of a drug trafficking crime. 

He pleaded guilty to the indictment without an agreement. In its presentence investigation 

report (PSR), the probation office determined that Gray was responsible for 1,528 grams of heroin 

and fentanyl analogues and 992.5 grams of cocaine base, or crack cocaine. Converted to 15,280 
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kilograms and 992.5 kilograms, respectively, he was responsible for 16,272.5 kilograms of converted 

drug weight.1 It thus recommended an initial base offense level of 34. USSG § 2D1.1(c)(3). 

The PSR also suggested three enhancements and one reduction. For engaging in a pattern of 

criminal conduct as a livelihood, it applied the two-level increase of § 2D1.1(b)(16)(E). Another 

increase of four levels applied under § 3B1.1(a) because of his leadership role. And the PSR applied 

a two-level increase under § 3C1.2 for fleeing from police in a residential area. After a three-level 

decrease for acceptance of responsibility, § 3E1.1, the resultant offense level of 39 and criminal 

history category of VI produced a 360-months to life guidelines range recommendation. 

Gray objected to the drug quantity calculation and to each recommended enhancement.2 

In response, the government presented testimony from Drug Enforcement Administration Task 

Force Officer Orlando Almonte at the sentencing hearing. Officer Almonte first addressed the 

drug quantity calculation. He explained that both Gray’s personal phone and the customer phone 

were intercepted from October to December 2018. For forty-eight days, officers tracked any 

transaction agreed to over these phones. They also tested drugs seized during traffic stops or in 

controlled buys. Lab results confirmed that the heroin was most often a mixture of heroin and 

fentanyl or its analogues. The crack cocaine seized generally was not mixed with other 

substances. Officer Almonte testified that these tested samples were a fair representation of the 

organization’s usual product. 

Gray nevertheless argued that because he did not plead guilty to some conduct mentioned 

in Officer Almonte’s testimony and the PSR, the district court should err conservatively and apply 

1 The parties do not address a miscalculation here: 992.5 grams of cocaine base would convert to approximately 

3,544.2 kilograms, not 992.5 kilograms, of converted drug weight. See USSG § 2D1.1 cmt. n.8(D) (converting one 

gram of cocaine base to 3,571 grams of converted drug weight). This undercounting did not affect Gray’s offense 

level. USSG § 2D1.1(c)(3). 

2 He ultimately declined to pursue his initial objection to the lifestyle enhancement of § 2D1.1(b)(16)(E), so we do 

not address it here. 
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an offense level of 32. It declined and stuck with the recommended offense level of 34, finding 

that the government established the drug quantity by a preponderance of the evidence based on the 

testimony, the lab reports, and the wide-ranging nature of the conspiracy. Further, officers counted 

only transactions agreed to over intercepted phone lines during the forty-eight day period. Because

the deal must have been clear on substance and quantity or price, many drug deals were 

undoubtedly excluded from the calculation. 

Gray next argued that his role in the conspiracy warranted only the two-level increase of 

§ 3B1.1(c), but not the four-level increase of subsection (a).

3

 The district court again heard from 

Officer Almonte, who testified that dealers had to go through Gray to access the customer phone 

and sell drugs. He also organized testers to sample the product and determine its potency. Even 

from jail, Gray gave his co-conspirators instructions on replacing the customer phone. Based on 

this testimony and the conduct described in the PSR, the district court overruled Gray’s objection 

to the four-level increase. 

Finally, Gray objected to the two-level increase for reckless endangerment during flight. 

The government justified the enhancement with two incidents: a pursuit on September 6, 2018, in 

a residential area near a school zone at speeds of over 60 miles per hour, and a high-speed pursuit 

on January 8, 2019, on Interstate 90 and the streets of Cleveland where, after stopping his vehicle, 

Gray dropped a loaded pistol before fleeing on foot. He admitted to these incidents. But, he said, 

the government did not establish the potential risk of harm. Unpersuaded, the district court 

overruled the final objection. 

The district court then turned to determining a proper sentence. It heard from the mother 

of an overdose victim who purchased his drugs from a member of the Grovewood Boys. Gray and 

3 On appeal, Gray acknowledges that § 3B1.1(c) could not apply to this conspiracy of five or more people. 
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his counsel also had the opportunity to address the court, and the government sought a life 

sentence. The district court then weighed each of the factors of 18 U.S.C. § 3553(a), focusing on 

the size of the conspiracy, Gray’s attempts to flee from law enforcement, and his prior convictions. 

It paid particular attention to the effects of Gray’s drug dealing on his community and his lack of 

remorse for the damage it caused. Finding a lengthy sentence essential, it imposed an aggregate

480-month term of imprisonment. 

Shondell Mack. Mack’s role in the Grovewood Boys was not quite so large. He was one 

of many dealers who operated the customer phone. Ultimately, he was indicted on one conspiracy 

charge and one count of using a communication facility in furtherance of a drug trafficking crime. 

He pleaded guilty with a plea agreement. 

Mack and the government agreed to recommend a within-guidelines sentence to the district 

court. Initially, that range was calculated at 37–46 months. But at his first sentencing hearing, the 

district court gave “the parties notice of a substantial possible upward variance” because that range 

“may not be anywhere near sufficient[:]” 

We have a defendant here who is on bond and commits three separate drug 

offense—or two drug offense-related cases, not to mention the federal case, and 

then is involved in a very serious matter . . . involving the theft of 60 stolen 

firearms. So I’m going to make sure both sides have a fair opportunity to argue. I 

contemplate a substantial upward variance from the guidelines based upon 

everything I’ve just indicated.

The district court gave the parties over a month to prepare for a second hearing. 

Prior to that sentencing hearing, an updated PSR suggested a 57–71 month guidelines 

range. Mack and the government agreed to that calculation. But the district court found it 

insufficient to meet the goals of § 3553(a). For one, it found Mack was “an extremely high risk 

offender” because of his history of violence towards women and his numerous prior arrests. It 
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also determined that a variance was necessary to protect the public from Mack and deter him from 

future crimes. Varying upward, it imposed a 96-month sentence. 

Larry Jackson. Jackson, another Grovewood Boy, also dealt drugs. He was indicted on 

one conspiracy charge, two charges of possession with intent to distribute, and one charge of using 

a communication facility in furtherance of a drug trafficking crime. He pleaded guilty and was 

sentenced to a 210-month term of imprisonment. His appeal concerns only the validity of his 

guilty plea, so we focus here on the facts surrounding that process.

Recall that twenty-two defendants were named in the indictment. So, when the district 

court held its first status conference on April 3, 2019, it emphasized the need for a cutoff date for 

guilty pleas. By mid-May, the district court decided on a plea deadline of August 12, 2019. 

Jackson received an offer by that date, but he rejected it at an August 14 hearing. To ensure he 

would not suffer any “buyer’s remorse,” the district court discussed the terms of that proposed 

agreement with Jackson at the hearing. 

New information about Jackson’s career offender status apparently changed his decision. 

He moved on August 30 for an extension of the plea deadline. A change of plea hearing was set 

for the next week but cancelled by the district court for reasons unspecified in our record. Jackson 

again notified the district court of his intent to change his plea on September 27, prior to a 

September 30 pretrial conference. 

The parties came to the pretrial conference with the previously rejected plea agreement, 

saying new “highly material and highly inculpatory evidence,” along with Jackson’s likely career 

offender status, explained the delay. Jackson was now ready to accept the agreement. But the 

district court rejected the parties’ reasons for the late agreement:

[I]f you think I’m going to take a plea today and he is going to get acceptance of 

responsibility when we have a week between now and trial, after everyone else 
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came in here and pled guilty timely, then you have another thing coming. . . . And 

candidly I don’t know why I should take it at all. My order says if you’re going to 

enter a plea, any plea after the date of the plea deadline will be to the indictment. 

And this is a last-minute hearing that we had now scheduled on a Plea Agreement 

that he could have considered some time ago.

If he wants to plead to the indictment, I’ll accept the plea. I’m not taking a Plea 

Agreement in this case right now. . . . Deadlines mean something, Counsel. Don’t 

ignore them willfully.

Jackson ultimately decided to plead guilty to the indictment, and the district court conducted a full 

change-of-plea hearing before accepting his guilty plea. 

II.

Both Gray and Mack appeal their sentences, and we review them for procedural and 

substantive reasonableness. A sentence is procedurally reasonable when the district court properly 

calculates the guidelines range, considers the sentencing factors in 18 U.S.C. § 3553(a), and 

adequately explains the sentence imposed. Gall v. United States, 552 U.S. 38, 51 (2007). We 

determine whether a sentence is procedurally reasonable under the abuse-of-discretion standard of 

review. United States v. Rayyan, 885 F.3d 436, 440 (6th Cir. 2018) (citing United States v. Bolds, 

511 F.3d 568, 579 (6th Cir. 2007)). The district court’s “factual findings will stand unless clearly 

erroneous,” and its legal conclusions are reviewed de novo. Id.

If procedurally sound, we assess the sentence’s substantive reasonableness. “The essence 

of a substantive-reasonableness claim is whether the length of the sentence is ‘greater than 

necessary’ to achieve the sentencing goals set forth in 18 U.S.C. § 3553(a).” United States v. 

Tristan-Madrigal, 601 F.3d 629, 632–33 (6th Cir. 2010); see also United States v. Walls, 546 F.3d 

728, 736 (6th Cir. 2008) (“A sentence is substantively unreasonable if the district court selects the 

sentence arbitrarily, bases the sentence on impermissible factors, fails to consider pertinent § 3553 

factors or gives an unreasonable amount of weight to any pertinent factor.” (cleaned up)). 

Substantive reasonableness is also reviewed for abuse of discretion. United States v. Wandahsega, 
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924 F.3d 868, 886 (6th Cir. 2019) (citing Gall, 552 U.S. at 51). And because balancing the 

§ 3553(a) factors “is a matter of reasoned discretion, not math,” our review here is “highly 

deferential.” Rayyan, 885 F.3d at 442 (citing Gall, 552 U.S. at 51).

A. GRAY’S SENTENCE

1. Procedural Reasonableness

Gray challenges three aspects of the district court’s calculation of his guidelines range: its 

drug quantity calculation and its application of the leadership-role and reckless-endangerment 

increases. We address each in turn. 

Drug Quantity. When a defendant is held responsible for drugs not seized by law 

enforcement, a district court must approximate the drug quantity. See USSG § 2D1.1 cmt. n.5. 

We must accept that approximation “unless clearly erroneous.” United States v. Walton, 908 F.2d

1289, 1300–01 (6th Cir. 1990) (citing United States v. Barrett, 890 F.2d 855, 867 (6th Cir. 1989)). 

A district court avoids clear error here by following several rules: facts must “have some minimal 

indicium of reliability beyond mere allegation,” United States v. Smith, 887 F.2d 104, 108 (6th 

Cir. 1989) (quotation omitted); any amount attributed to the defendant’s conspiracy must be known 

or reasonably foreseeable to the defendant, Walton, 908 F.2d at 1301; and the court should “err on 

the side of caution in making its estimate,” United States v. Sandridge, 385 F.3d 1032, 1037 (6th 

Cir. 2004) (quoting United States v. Owusu, 199 F.3d 329, 338 (6th Cir. 2000)). Ultimately, we 

will not second-guess “[a]n approximation . . . supported by competent evidence in the record.” 

United States v. Ward, 68 F.3d 146, 149 (6th Cir. 1995). 

The district court’s calculation here was fully supported by competent evidence in the 

record. It heard testimony that law enforcement intercepted phones for forty-eight days, counting 

only drug transactions where substance and an agreed quantity or price were confirmed. Officers 
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tested drugs seized from the conspiracy to confirm that fentanyl and its analogues were present in 

almost all heroin. Further, because of the short window of intercepted calls, that final figure left 

out a significant amount of drug sales attributable to Gray. See United States v. Jeross, 521 F.3d 

562, 571 (6th Cir. 2008) (citation omitted) (“[T]he district court appropriately exercised caution” 

where a defendant “was more likely actually responsible for a quantity greater than or equal to the 

amount used in calculating the sentence.” (citation omitted)).

Gray did not contest the government’s evidence. Rather, he urged the district court to “err[] 

conservatively for an offense level of 32, rather than 34, based on what was actually pled guilty 

to.” He makes a similar argument here, suggesting that erring on the side of caution requires 

“taking a conservati[ve] estimate then discounting that estimate to protect the defendant’s due 

process rights.” Not so. A court errs on the side of caution when, presented with “a number of 

plausible estimates of drug quantity, none of which is more likely than not the correct quantity,” it 

selects the quantity supported by a preponderance of the evidence. Walton, 908 F.2d at 1302. The 

district court here was given one plausible, conservative estimate and determined it was supported 

by competent evidence. 

Now on appeal, Gray argues for the first time that the district court erred by counting 1,528 

grams of fentanyl analogue and 922.5 grams of cocaine base, when, in his view, those substances 

were present in only some of the drugs. This new argument is entitled only to plain-error review. 

United States v. Johnson, 627 F.3d 578, 585 (6th Cir. 2010) (citation omitted). But Gray can only 

argue error occurred by ignoring the evidence in the record. The district court heard testimony 

that the vast majority of the Grovewood Boys’ heroin contained fentanyl or its analogues and their 

cocaine was almost always crack cocaine. It cited this testimony, lab reports, and other 
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uncontested facts in overruling Gray’s objections. Its reliance on this evidence did not affect 

Gray’s substantial rights. 

Leadership Role. A sentencing court can apply a four-level increase when a defendant 

organized or led a criminal activity involving five or more people. USSG § 3B1.1(a). To qualify, 

he “must have exerted control over at least one individual” within the conspiracy. United States 

v. Gort-Didonato, 109 F.3d 318, 321 (6th Cir. 1997). Neither being an essential part of a 

conspiracy nor managing its property makes a defendant a leader or organizer. United States v.

Christian, 804 F.3d 819, 824 (6th Cir. 2015); United States v. Vandeberg, 201 F.3d 805, 811–12 

(6th Cir. 2000) (citing United States v. Albers, 93 F.3d 1469, 1487 (10th Cir. 1996)). Instead, 

courts look to a defendant’s receipt of a larger share of profits, recruitment of co-conspirators, 

planning, special expertise, providing special information to facilitate the crime, or issuing orders. 

See Christian, 804 F.3d at 825 (collecting cases). We review the district court’s factual findings 

for clear error and defer to its conclusion that Gray led this conspiracy. Id. at 822 (citing United 

States v. Washington, 715 F.3d 875, 982–83 (6th Cir. 2013)).

Gray argues that his occasional control of the customer phone makes him a manager, but not 

a leader, of the Grovewood Boys. But the district court did not only find that Gray controlled the 

customer phone; it also heard testimony that Gray decided who could access the phone, instructed 

others on replacing the phone, and organized people to test the drugs prior to sale. In addition, the 

court relied on the uncontested facts in the PSR, including Gray’s involvement in monitoring drug 

supplies, obtaining bulk quantities of drugs, and coordinating the sale by other co-conspirators. It 

did not err in determining that Gray was a leader or organizer of this conspiracy.

Reckless Endangerment. The guidelines also call for a two-level offense level increase where 

a defendant recklessly endangers others while fleeing from law enforcement. USSG § 3C1.2. His 
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flight must create a substantial risk of death or serious bodily injury to another person and be 

sufficiently related to the offense of conviction. United States v. Dial, 524 F.3d 783, 786–87 (6th 

Cir. 2008) (quoting United States v. Southerland, 405 F.3d 263, 268 (5th Cir. 2005)). This “mixed 

question of law and fact” is “highly fact-based,” so “we give ‘significant deference to the district 

court.’” Id. at 785 (quoting United States v. Hazelwood, 398 F.3d 792, 796 (6th Cir. 2005)). Here, 

the district court applied the enhancement based on both of Gray’s flights from law enforcement. 

Gray makes two arguments on appeal, both meritless. He first suggests that the September 

6 incident—where an attempted traffic stop became a pursuit at over 60 miles per hour in a 

residential neighborhood—was not related to the offenses of conviction. The indictment suggests 

otherwise, as it charges Gray with flight from police during the conspiracy. The record also states 

that traffic stops were a common method used by law enforcement to apprehend members of the 

conspiracy. Our caselaw further suggests that defendants who flee from law enforcement during 

the timeframe of a conspiracy’s existence and in its geographic area of operation readily meet the 

nexus requirement. Dial, 524 F.3d at 788–89.

He also argues that his January 8 flight “shows no more than ordinary risk, not substantial

risk of serious bodily injury[.]” Uncontested evidence of “a high speed chase where others are 

likely to be nearby” alone meets the substantial risk requirement of § 3C1.2. See Hazelwood, 398 

F.3d at 796 (collecting cases). The loaded pistol he dropped while continuing his flight further 

weakens his claim. See United States v. Stafford, 721 F.3d 380, 402 (6th Cir. 2013) (citing United 

States v. Howard, 301 F. App’x 446, 449 (6th Cir. 2008)) (upholding a § 3C1.2 enhancement 

where a defendant discarded a loaded gun in a public place). The district court committed no error 

in applying this enhancement.
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2. Substantive Reasonableness

Turning now to substantive reasonableness, Gray faces the “presumption of 

reasonableness” we apply to a within-guidelines sentence. Gall, 552 U.S. at 51 (citing Rita v. 

United States, 551 U.S. 338, 347 (2007)). He argues that the district court over-emphasized any 

need to protect the public. But his argument amounts to a request that we “balance the factors 

differently than the district court did.” United States v. Ely, 468 F.3d 399, 404 (6th Cir. 2006). 

Such re-balancing is “beyond the scope of our appellate review.” Id.; see also United States v. 

Pyles, 904 F.3d 422, 426 (6th Cir. 2018) (“We have no warrant to reweigh the § 3553(a) factors 

ourselves.”). As we noted above, applying § 3553(a) involves “reasoned discretion, not math.” 

Rayyan, 885 F.3d at 442. The district court here faced a defendant who had dealt a significant 

amount of drugs and showed no remorse for his crimes or their consequences. It did not abuse its 

discretion in imposing a within-guidelines sentence on this record. 

B. MACK’S SENTENCE

1. Procedural Reasonableness

Mack argues that the district court erred procedurally in failing to conduct an upward 

departure analysis before varying upward at sentencing. But when given the opportunity at 

sentencing, he failed to object. United States v. Bostic, 371 F.3d 865, 872–73 (6th Cir. 2004). 

Accordingly, we review the district court’s decision to apply an upward variance for plain error. 

United States v. Rosenbaum, 585 F.3d 259, 266–67 (6th Cir. 2009) (citing United States v. Vonner, 

516 F.3d 382, 386 (6th Cir. 2008) (en banc)). To prevail under this standard, Mack must show an 

obvious or clear error that affected both his substantial rights and “the fairness, integrity, or public 

reputation of the judicial proceedings.” United States v. Hall, 979 F.3d 1107, 1119 (6th Cir. 2020) 

(quoting United States v. Wells, 623 F.3d 332, 337 (6th Cir. 2010)).
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First, to clarify a confusion in Mack’s argument: a “departure” happens when a district court 

applies a particular guidelines provision to impose a sentence outside the advisory range or assign a 

different criminal history category, while a “variance” occurs when the district court selects a 

sentence outside the guidelines range after weighing the factors of 18 U.S.C. § 3553(a). United 

States v. Grams, 566 F.3d 683, 686–87 (6th Cir. 2009). The two concepts are distinct; hence, the 

procedures associated with a departure are not required when a district court varies upward. United 

States v. Denny, 653 F.3d 415, 419–20 (6th Cir. 2011). We have said “it behooves a district court to 

indicate clearly whether it is ‘departing’ or ‘varying’ when it elects to deviate from the sentencing

guidelines.” Id. (citing United States v. Stewart, 628 F.3d 246, 259 (6th Cir. 2010)).

Here, the district court varied upward, so Mack’s procedural arguments falter. A district 

court need not provide notice when “contemplating a variance.” Irizarry v. United States, 553 

U.S. 708, 714–16 (2008). Rather, it should “make sure that the information provided to the parties 

in advance of the hearing, and in the hearing itself, has given them an adequate opportunity to 

confront and debate the relevant issues.” Id. at 715. It did so here. The parties knew the district 

court was considering “a substantial possible upward variance” and were given an additional 

month to prepare to address the issues. And at sentencing, the district court considered the 

§ 3553(a) factors alongside the uncontested facts in the record when explaining its decision to vary 

upward. This was not plain error. 

2. Substantive Reasonableness

Mack also claims that his sentence was substantively unreasonable. We again conduct a 

“highly deferential” review of the district court’s balancing of the factors of § 3553(a). Rayyan, 885 

F.3d at 442 (citing Gall, 552 U.S. at 51). This above-guidelines sentence “is neither presumptively 

reasonable nor presumptively unreasonable.” United States v. Robinson, 892 F.3d 209, 212 (6th Cir. 
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2018) (citing United States v. Robinson, 813 F.3d 251, 264 (6th Cir. 2016)). And in imposing it, the 

district court must have “consider[ed] the extent of the deviation and ensure[d] that the justification 

is sufficiently compelling to support the degree of the variance.” Gall, 552 U.S. at 50.

The district court did not abuse its discretion by varying upward. As it noted, the district 

court was not required to follow the guidelines. Gall, 552 U.S. at 49–50. After considering Mack’s 

history with drugs, firearms, and domestic violence, along with the leniency he had received in state 

court, it determined that the guidelines recommendation was not sufficient to protect the public and 

deter future criminal behavior. It then imposed a 96-month term of imprisonment, 25 months above 

the upper-end of Mack’s guidelines range. We do not weigh the sentencing factors anew. Ely, 468 

F.3d at 404. Rather, we only confirm that the district court “properly considered” each of the factors 

of § 3553(a) and “gave ample explanation” for its upward variance. United States v. Bass, 785 F.3d 

1043, 1052 (6th Cir. 2015). It did, so the sentence was substantively reasonable.

III.

Lastly, we address Jackson’s argument that his guilty plea was invalid. In his view, the 

district court exerted undue influence over him and, in doing so, violated Federal Rule of Criminal 

Procedure 11(c). Because he makes this argument for the first time on appeal, we review for plain 

error. See United States v. Webb, 403 F.3d 373, 378 (6th Cir. 2005) (quoting United States v. Vonn, 

535 U.S. 55, 59 (2002)) (requiring defendants “to object contemporaneously to the district court’s 

alleged failure to comply with the requirements of Rule 11” to avoid plain-error review). So he “can 

prevail only if he shows that the district court made a plain error that affected his substantial rights 

and the fundamental fairness of the sentencing proceeding.” United States v. Pyles, 904 F.3d 422, 

426 (6th Cir. 2018) (citing United States v. Vonner, 516 F.3d 382, 385–86 (6th Cir. 2008) (en banc)).
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Rule 11(c) proscribes a district court’s participation in plea discussions. FED. R. CRIM. P.

11(c)(1). Additionally, a guilty plea must be entered voluntarily, knowingly, and intelligently. 

Brady v. United States, 397 U.S. 742, 748 (1970). Pleas are voluntary when the defendant 

understands the charges against him and the constitutional protections he is waiving, and they are 

knowing and intelligent if he is aware of the circumstances and consequences of his decision. See 

Henderson v. Morgan, 426 U.S. 637, 645 n.13 (1976); Brady, 397 U.S. at 748. Jackson says his 

plea was not made voluntarily or intelligently because the district court set a plea deadline, 

threatened to deny an acceptance of responsibility decrease after untimely pleas, and discussed a 

rejected plea agreement with Jackson. None of those actions constitute plain error.

To start, the plea deadline in this case was not designed to encourage guilty pleas. The 

district court told all twenty-two defendants that “[n]o one is suggesting you must [plead guilty], 

or it’s not the purpose of the suggestion, but there has to be a deadline, a deadline by which the 

parties can complete if they would like and that also will be a date, if they wish, [that] will have 

implications for acceptance of responsibility.” Far from a device used to manipulate defendants 

into pleading guilty, the record shows that this deadline allowed the district court to manage this 

complicated criminal matter. Jackson can identify no authority disallowing a district court’s 

management of its case in this way.

Nor can he show that the district court’s discussion of his acceptance of responsibility credit 

was plain error. We have held that “[d]istrict courts may consider the timeliness of a defendant’s 

plea under § 3E1.1(a) only to the extent that timeliness reflects the extent of the defendant’s sincerity 

in accepting responsibility.” United States v. Hollis, 823 F.3d 1045, 1047–48 (6th Cir. 2016) (citing 

United States v. Kumar, 617 F.3d 612, 637 (2d Cir. 2010)). And nothing in the district court’s 

suggestion that the plea deadline “will have implications for acceptance of responsibility” signals its 
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intention to ignore the limits of Hollis. So Jackson’s arguments amount to an invitation to reverse 

his convictions because the district court, in implementing a plea deadline, promised to consider a 

relevant factor when calculating his offense level. We decline that invitation.

Finally, Jackson suggests the district court erred in discussing a proposed plea agreement 

with him to confirm he rejected it. But the district court made clear that Jackson had no obligation 

to accept the plea agreement; it merely sought confirmation that Jackson knew the terms of the 

rejected offer to avoid a later claim that he would have accepted the offer had he been fully aware of 

it. And when Jackson later sought to accept the agreement one week before trial, this discussion 

became relevant to the district court’s decision to enforce its plea cutoff date. The district court did 

not improperly engage in plea discussions by explaining the consequences of rejecting the plea offer.

In short, no plain error occurred here. The district court permissibly enforced a plea 

deadline. And in accepting Jackson’s guilty plea to the counts in the indictment, and at each step 

prior to that point, it ensured Jackson was aware of the charges against him and the consequences 

of his decision to plead guilty. We have no reason to doubt the validity of Jackson’s choice.

IV.

Gray and Mack’s sentences were both procedurally and substantively reasonable. And the 

district court committed no plain error in accepting Jackson’s knowing and voluntary guilty plea. 

We therefore affirm. 
Case Nos. 20-3019/3223/3393, United States v. Gray, et al.

-17-

SILER, Circuit Judge, concurring. I concur in the majority opinion in full, but I bring 

attention to the two-level offense increase for Gray under USSG § 3C1.2 when he recklessly drove 

a vehicle when fleeing from law enforcement. The majority opinion indicates that in order to 

impose this increase, the defendant’s flight from law enforcement must create a substantial risk of 

death or serious bodily injury to another person “and be sufficiently related to the offense of the 

conviction,” citing United States v. Dial, 524 F.3d 783, 786-787 (6th Cir. 2008). Although our 

court held in Dial that the increase must be based on conduct which is related to the offense of 

conviction, I then felt that it was “not necessary to find a nexus requirement embedded in USSG 

§ 3C1.2,” and I would do so in this case if it were not for the majority opinion in Dial. The 

language in § 3C1.2 does not require a nexus to the offense. Nevertheless, the flight which led to 

the enhancement in this case was a charged overt act in the conspiracy, so the reckless conduct 

was related to the offense charged.