Young

IN THE UNITED STATES DISTRICT COURT

FOR THE SOUTHERN DISTRICT OF ILLINOIS

DUSTY YOUNG,

Petitioner,

v. Case No. 3:22-CV-02470-NJR

UNITED STATES OF AMERICA,

Respondent.

MEMORANDUM AND ORDER

ROSENSTENGEL, Chief Judge:

This matter is before the Court on Petitioner Dusty Young’s motion to vacate his

conviction and sentence pursuant to 28 U.S.C. § 2255. (Doc. 1). Young contends that his

conviction and corresponding sentence for participating in a methamphetamine

distribution conspiracy must be vacated because he received ineffective assistance from

his trial counsel in violation of his Sixth Amendment rights. For the reasons set forth

below, Young’s section 2255 motion is denied.

BACKGROUND

Young was charged in February 2019 with conspiracy to distribute and possession

with intent to distribute methamphetamine in violation of 21 U.S.C. § 841(a)(1) and

841(b)(1)(A)(viii). See United States v. Young, No. 3:19-cr-30018-NJR-4 (S.D. Ill.), Doc. 1.

The indictment alleged that the total amount of methamphetamine involved in the

conspiracy was contained in a substance weighing more than 500 grams.

Young appeared before the Court for a change of plea hearing on September 11,

2019, where he was represented by attorney Jordan J. Campanella. He was placed under

oath and was warned that he could be charged with perjury if he lied, which he indicated

that he understood. (Doc. 8-1 pp. 3-4). The undersigned then asked Young questions

relevant to determining his competency and ability to understand the proceedings.

Young represented that he could read and write, denied any recent treatment for mental

health issues, and denied being under the influence of alcohol, drugs, or medications.

(Id. at pp. 5-6). The undersigned then explained to Young the right to trial and associated

rights that he was waiving by pleading guilty. (Id. at pp. 6-10). Young affirmed that he

wished to give up those rights by pleading guilty. (Id. at p. 10). As part of his plea

agreement, Young stated that he was satisfied with his attorney’s representation and

when asked by the undersigned whether he had questions about that portion of the plea

agreement, he responded that he did not. (Id. at pp. 15-16).

After the Government explained the elements of the conspiracy charge, the

undersigned reminded Young that he faced a mandatory minimum sentence of 10 years

in prison, up to a maximum of life in prison, along with a $10 million fine, a 5-year

minimum term of supervised release, and a $100 special assessment. (Id. at p. 11-12).

Young affirmed that he understood those possible penalties. (Id. at p. 12).

The undersigned then addressed the voluntariness of Young’s plea. Young denied

that anyone had pressured or forced him to plead guilty. (Id. at p. 13). The undersigned

explained the nature of the sentencing guidelines and asked Young if he had discussed

the advisory character of the guidelines with Mr. Campanella, which Young affirmed.

(Id. at pp. 13-14, 16-17). The undersigned also explained that the plea agreement included

a waiver of certain rights to seek review of his conviction that would restrict his ability

“to seek modification of, or contest any aspect of the conviction, or sentence, in any type

of proceeding.” (Id. at p. 15). The waiver provided that Young would forgo any right to

bring a collateral attack to the constitutionality of the statute to which he pleaded guilty

or to later argue his conduct fell outside the statute’s scope. (Young, No. 3:19-cr-30018-

NJR-4 (S.D. Ill.), Doc. 145, pp. 9-10). However, Young did not waive his right to argue on

appeal or in a collateral proceeding that he had received ineffective assistance of counsel.

(Id. at p. 10).

After the Government reviewed the factual stipulation supporting the plea, Young

stated that he agreed with the facts as described by the Government and denied having

any questions. (Doc. 8-1 pp. 19-20). Young then affirmed that his decision to plead guilty

was based on his own free will. (Id. at pp. 20-21). Finding Young’s guilty plea entered

knowingly and voluntarily, the undersigned accepted his plea. (Id. at p. 21).

Following Young’s guilty plea, the United States Probation Office prepared an

initial presentence report (“PSR”). (Young, supra, Doc. 131). The PSR recommended—and

the parties agreed—to a base offense level of 34 because the conspiracy involved 5.188

kilograms of a substance containing methamphetamine. (Id. at p. 7). The parties also

agreed that Young was subject to the career offender enhancement found in Section 4B1.1

of the Sentencing Guidelines, increasing his offense level by an additional three levels.

(Id.). Young received a three-level reduction for his acceptance of responsibility. (Id.). His

ultimate guideline range of 262 to 327 months imprisonment was driven, in large part,

by his lengthy criminal history and career offender designation, which placed in him

criminal history category VI. (Id. at p. 23).

In preparation for sentencing, Mr. Campanella filed a sentencing memorandum

and supplement. (Young, supra, Docs. 135, 136). He argued principally that Young’s

criminal history was overstated and that his conduct was influenced by his addiction. On

December 18, 2019, the Court sentenced Young to 244 months of imprisonment, below

the guideline range of 262 to 327 months, followed by five years of supervised release.

(Young, supra, Doc. 141).

Young did not file a direct appeal with the United States Court of Appeals for the

Seventh Circuit. Instead, on October 24, 2022, Young moved to vacate his conviction and

sentence under 28 U.S.C. § 2255. (Doc. 1). Upon preliminary review, the Court ordered

the government to file a response. (Doc. 2). Young later filed a reply brief. (Docs. 10).

LEGAL STANDARD

Section 2255 of Title 28 of the United States Code provides a federal prisoner with

a post-conviction remedy to test the legality of their detention “upon the ground that the

sentence was imposed in violation of the Constitution or laws of the United States.”

28 U.S.C. § 2255(a). “[R]elief under § 2255 is an extraordinary remedy because it asks the

district court essentially to reopen the criminal process to a person who already has had

an opportunity for full process.” Almonacid v. United States, 476 F.3d 518, 521 (7th Cir.

2007) (citing Kafo v. United States, 467 F.3d 1063, 1068 (7th Cir. 2006)). Thus, it “is available

only in extraordinary situations, such as an error of constitutional or jurisdictional

magnitude or where a fundamental defect has occurred which results in a complete

miscarriage of justice.” Blake v. United States, 723 F.3d 870, 878-79 (7th Cir. 2013) (citations

omitted).

DISCUSSION

Young contends that he is entitled to relief because his trial counsel was ineffective

in several respects. He says Mr. Campanella advised him to plead guilty “without

challenging the 851 enhancement,” failed to investigate whether his prior drug offenses

permitted an enhancement of his sentence under sections 841(a)(1) and (B)(1)(A) of Title

21, failed to contest the career offender enhancement under U.S.S.G. § 4B1.1, and

encouraged him to plead guilty with a plea agreement that contained a waiver of his

rights to appellate and collateral review (Claim I). (Doc. 1 pp. 4-5). Apart from his

ineffective assistance claims, Young argues his sentence is invalid because his prior

offenses in Missouri cannot be counted toward the career offender enhancement (Claims

II and III) and that the Court committed “plain error” “by applying a sentencing

enhancement pursuant to 841(b)(1)(A) and 851” (Claim IV). (Id. at pp. 7-8).

A. Timeliness

The government argues that Young’s motion is untimely. A motion for relief under

28 U.S.C. § 2255 is subject to a one-year limitations period, which runs from the latest of

four possible dates:

(1) the date on which the judgment of conviction becomes final;

(2) the date on which the impediment to making a motion created by

governmental action in violation of the Constitution or laws of the

United States is removed, if the movant was prevented from making

a motion by such governmental action;

(3) The date on which the right asserted was initially recognized by the

Supreme Court, if that right has been newly recognized by the

Supreme Court and made retroactively applicable to cases on

collateral review; or

(4) The date on which the facts supporting the claim or claims presented

could have been discovered through the exercise of due diligence.

28 U.S.C. § 2255(f).

In a typical case, the limitations period will begin to run under subsection (f)(1) of

§ 2255, or the date on which the challenged conviction becomes “final.” Id. § 2255(f)(1).

Where a defendant does not seek direct review, as here, finality coincides with the

expiration of the deadline to file a notice of appeal, see Clarke v. United States, 703 F.3d

1098, 1100 (7th Cir. 2013), generally 14 days after the entry of judgment, Fed. R. App. P.

4(b)(1)(A)(i). Here, Young’s conviction became final for purposes of 28 U.S.C. § 2255(f)(1)

on January 2, 2020—14 days from the date of judgment, plus an additional day because

the last day of the appeal period fell on New Year’s Day. See Fed. R. App. P. 26(a)(1)(C).

The limitations period would thus have expired one year later—on January 2, 2021.

Young, however, did not file his Section 2255 motion until October 24, 2022, nearly two

years after the deadline.

Attempting to explain the untimely filing, Young cites “Rule 52.” Most likely, he

refers to Federal Rule of Criminal Procedure 52, which provides that “[a] plain error that

affects substantial rights may be considered even though it was not brought to the court’s

attention.” Fed. R. Crim. P. 52(b). Young contends that his substantial rights were affected

by an impermissible enhancement to his sentence under 21 U.S.C. §§ 841 and 851, so the

error can be considered now.

At least two problems present. First, the “plain error” standard announced in that

rule “was intended for use on direct appeal” and “is out of place when a prisoner

launches a collateral attack against a criminal conviction . . . .” United States v. Frady,

456 U.S. 152, 164 (1982); United States v. Anaya, 736 F. App’x 205, 206 (10th Cir. 2018)

(“[T]he rule does not provide an independent legal basis for a collateral attack on a final

judgment.”). Put simply, there is no “plain error” exception to the time limitations

specified in § 2255(f). Perhaps the more fundamental problem, however, is that Young’s

sentence was not driven by any enhancement under 21 U.S.C. §§ 841(b)(1)(A) and 851 but

by the career offender sentencing guideline.

Young also attempts to explain his untimely filing by citing United States v. Ruth,

966 F.3d 642 (7th Cir. 2020), which he says establishes new law retroactive on collateral

review and restarts the deadline under subsection (f)(3). As the government aptly points

out, however, Ruth is a decision of the Seventh Circuit, not of the Supreme Court, as

would trigger that extended limitation period.

Of course, § 2255’s limitations period is not jurisdictional and is subject to equitable

tolling. Nolan v. United States, 358 F.3d 480, 483 (7th Cir. 2004). However, “the threshold

necessary to trigger equitable tolling is very high[.]” United States v. Marcello, 212 F.3d

1005, 1010 (7th Cir. 2000). A petitioner seeking equitable tolling “must show: (1) that [they

have] been pursuing [their] rights diligently; and (2) that some extraordinary

circumstance stood in [their] way and prevented timely filing.” Lombardo v. United States,

860 F.3d 547, 551 (7th Cir. 2017) (citing Holland v. Florida, 560 U.S. 631, 649 (2010)). In

establishing diligence, a petitioner must demonstrate their “reasonable effort throughout

the limitations period” beyond “mere conclusory allegations of diligence[.]” Mayberry v.

Dittmann, 904 F.3d 525, 531 (7th Cir. 2018) (citing Carpenter v. Douma, 840 F.3d 867, 870

(7th Cir. 2016)). Extraordinary circumstances exist only where an external factor beyond

the petitioner’s control caused the delay in filing. Lombardo, 860 F.3d at 552 (citing

Menominee Indian Tribe of Wis. v. United States, 577 U.S. 250, 257 (2016)).

Young offers two reasons tolling would be appropriate here: his lack of access to

prison library resources due to COVID protocols at several facilities where he resided

and a need to “check in” because he “help[ed] the gov. on cases.” (See Doc. 1 p. 11; Doc. 10

p. 2).

Equitable tolling “can extend the one-year period available for filing” when an

applicant experiences some extraordinary circumstance, beyond their control, that

prevents timely filing. Perry v. Brown, 950 F.3d 410, 412 (7th Cir. 2020); see generally Holland

v. Florida, 560 U.S. 631 (2010). The prisoner must also show that he has “diligently pursued

his claim, despite the obstacle.” Tucker v. Kingston, 538 F.3d 732, 734 (7th Cir. 2008).

“[S]imple legal errors, such as ignorance of the federal deadline, do not suffice.” Perry,

950 F.3d at 412. Even so, “the diligence required for equitable tolling purposes is

reasonable diligence . . . not maximum feasible diligence.” Moreland v. Eplett, 18 F.4th 261,

271 (7th Cir. 2021) (quoting Holland, 560 U.S. at 653) (cleaned up).

The Seventh Circuit has held that a prisoner’s limited access to the prison law

library is not grounds for equitable tolling. Tucker, 538 F.3d at 735 (citing Jones v. Hulick,

449 F.3d 784, 789 (7th Cir. 2006)). However, the court of appeals has also suggested that

a prisoner’s lack of access to a law library remains a relevant consideration, particularly

when coupled with the exigencies of the COVID-19 pandemic and other factors. See Lairy

v. United States, 142 F.4th 907, 917 (7th Cir. 2025) (remanding for an evidentiary hearing

to establish whether a prisoner was entitled to tolling where he claimed he was in

lockdown for the majority of the one-year filing period, lacked access to the law library

during these lockdowns, and, despite repeated requests to his former counsel, received

access to some of his case files a day before filing his amended petition). Simply referring

to the pandemic is not enough to establish extraordinary circumstances; a petitioner

must, at a minimum, provide an explanation of how COVID-19 prevented him from

timely filing his petition. United States v. Reeves, No. 14-1588, 2022 WL 17832713, at *7

(N.D. Ill. Dec. 21, 2022); see also Zuno v. Brannon-Dortch, No. 21-4786, 2023 WL 4083907, at

*6 (N.D. Ill. June 20, 2023); Katz v. U.S. Dep’t of Lab., 857 F. App’x 859, 864 (7th Cir. 2021).

In his reply brief, Young adds additional detail to his explanation. He states that

he was subject to strict quarantine protocols during the first two years of his incarceration

and had limited access to the law library. He avers that quarantine protocols in prison

affected his efforts between March 18, 2020, and March 1, 2021, and that he then was

placed in protective custody for nearly six months between March and September of 2021.

Then, he was transferred to a BOP facility in Oklahoma City for three weeks before being

placed into a quarantine at a new facility in Louisiana. Young says that he was “finally

put into [a] RHU unit” on October 27, 2021, but the facility had a lengthy waitlist of

inmates hoping to use the single computer in the law library. He also mentions a concern

regarding his cooperation with the government but does not explain in much detail.

Although an evidentiary hearing is necessary when a petitioner alleges facts that,

if true, would entitle him to relief, Mayberry, 904 F.3d at 532, “when a petitioner’s

allegations supporting equitable tolling are vague or conclusory, or when ‘the files and

records of the case conclusively show that the prisoner is entitled to no relief,’” no hearing

is needed. Lairy, 142 F.4th at 917 (quoting Mayberry, 904 F.3d at 532).

No evidentiary hearing is necessary here. Although the Court is sensitive to the

exigencies caused by the COVID-19 pandemic and is willing to credit that those

circumstances affected Young’s access to the law library, see id., that explanation only

takes him so far. The defendant in Lairy, for instance, also had to contend with extensive

delays by his former counsel in furnishing case files. Id. at 917; see also Socha v. Boughton,

763 F.3d 674, 686 (7th Cir. 2014) (holding that equitable tolling was appropriate where the

prisoner was without access to most of the documents pertaining to his case for the

majority of the limitations period and, when finally able to access his documents, could

not bring them to his cell to review them).

By Young’s own account, his living conditions within his prison facilities had

returned to some degree of normalcy by October 27, 2021, and he had access to a law

library at that time. Yet he did not file his 2255 motion until October 24, 2022—nearly a

year later. The only explanation he offers for that delay is a lengthy backlog of prisoners

hoping to use a single computer in his prison’s law library. But if a lack of access to a law

library is insufficient in this Circuit, it is not clear why a lack of access to a computer in

the library would be. More than that, Young offers no specific details regarding how he

exercised reasonable diligence during the years-long delay, notwithstanding the

computer backlog. He alludes to a need to “check in” due to his cooperation with the

government on cases, but much about this rationale is left unexplained. Who did he need

to “check in” with? Why would assisting the government hamper his ability to file

timely? Why did the “check in” process take so long? Young’s allegations are wholly

insufficient to justify equitable tolling. No hearing is necessary to assess his entitlement

to that relief. Ademiju v. United States, 999 F.3d 474, 478 (7th Cir. 2021).

For these reasons, the Court concludes that the Section 2255 motion is procedurally

barred as untimely.

B. Waiver

Even if Young were entitled to tolling of the filing deadline, his claims would fail

on the merits. As an initial matter, the Government observes that Young waived his right

to collaterally attack his sentence for most reasons as part of his plea agreement. The

Government is correct. Young bargained away his right to collaterally attack his

conviction on most grounds other than if his sentence exceeded the Sentencing

Guidelines or for claims that he received ineffective assistance of counsel. (Young, supra,

Doc. 123, pp. 9-10). The Seventh Circuit has held that a knowing and voluntary waiver of

the right to appeal or to collaterally attack a conviction and sentence is valid and

enforceable. See Jones v. United States, 167 F.3d 1142, 1145 (7th Cir. 1999); see also Keller v.

United States, 657 F.3d 675, 681 (7th Cir. 2011). “But for a waiver to apply, the disputed

appeal or collateral attack must fall within the waiver’s scope.” Dowell v. United States,

694 F.3d 898, 902 (7th Cir. 2012). After all, a plea agreement is a contract, and the terms of

the agreement are interpreted according to the reasonable expectations of the parties with

any ambiguities construed in the light most favorable to the criminal defendant. Id. Still,

the enforceability of waiver provisions is subject to a few exceptions. A defendant retains

the right to challenge:

(1) a sentence based on constitutionally impermissible criteria, such as race;

(2) a sentence that exceeds the statutory maximum for the defendant’s

particular crime; (3) deprivation of some minimum of civilized procedure

(such as if the parties stipulated to trial by twelve orangutans); and

(4) ineffective assistance of counsel in negotiating the plea agreement.

United States v. Adkins, 743 F.3d 176, 192-93 (7th Cir. 2014) (quoting United States v. Bownes,

405 F.3d 634, 637 (7th Cir. 2005)).

Young does not develop an argument that his claims, with the obvious exception

of his ineffective assistance of counsel claims, are outside the scope of the waiver’s plain

terms. He also does not argue that he unknowingly or involuntarily entered the waiver.

Indeed, he confirmed he understood the waiver on the record during his change of plea

hearing. (Doc. 8-1, p. 15). The undersigned found that Young was competent to plead

guilty, and he does not now contend otherwise. Thus, all of Young’s claims, except for

his ineffective assistance of counsel claims, must also be dismissed for this reason.

C. Ineffective Assistance

Young’s ineffective assistance claims indisputably lack merit. A Sixth Amendment

claim of ineffective assistance of counsel is analyzed under the Supreme Court’s two-

prong test set forth in Strickland v. Washington, 466 U.S. 668 (1984). First, the petitioner

must show that counsel’s performance was deficient, “meaning it fell below an ‘objective

standard of reasonableness’ informed by ‘prevailing professional norms.’” McElvaney v.

Pollard, 735 F.3d 528, 532 (7th Cir. 2013) (quoting Strickland, 466 U.S. at 688). The petitioner

also must show that “counsel’s deficient performance prejudiced him, meaning that there

is a ‘reasonable probability that, but for counsel’s unprofessional errors, the result of the

proceeding would have been different.’” McElvaney, 735 F.3d at 532 (quoting Strickland,

466 U.S. at 688). “[T]he Sixth Amendment right to effective assistance of counsel extends

to assistance rendered when deciding whether to reject a plea offer.” Almonacid v. United

States, 476 F.3d 518, 521 (7th Cir. 2007). But in light of the waiver provisions contained in

Young’s plea agreement, he must do more than “assert that a constitutional violation

preceded his decision to plead guilty or that his trial counsel was ineffective for failing to

raise the constitutional claim.” Hurlow v. United States, 726 F.3d 958, 966 (7th Cir. 2013).

“[H]e must allege that the plea agreement was the product of ineffective assistance of

counsel or tainted by ineffective assistance of counsel.” Id. at 967 (citations omitted).

A court may address the elements of the Strickland test “in whichever order is most

expedient.” Watson v. Anglin, 560 F.3d 687, 690 (7th Cir. 2009). Moreover, where a claim

of ineffective assistance fails on one prong, the court need not address the other prong

insofar as the failure to satisfy either prong is fatal to the claim. See Ebbole v. United States,

8 F.3d 530, 533 (7th Cir. 1993).

None of Young’s ineffective assistance arguments persuade. He first alleges that

Mr. Campanella fell below professional standards expected of counsel by advising him

to plead guilty “without challenging the 851 enhancement” or investigating whether his

prior drug offenses qualified as predicates for the enhancement. (Doc. 1 p. 4). It appears

that Young is referring to the alternative mandatory minimum penalties contained in

21 U.S.C. § 841 for individuals convicted of certain prior offenses. However, the

Government never filed an information under 21 U.S.C. § 851 detailing Young’s prior

offenses, as would have been necessary to trigger those enhanced penalties. Young’s

attorney was not ineffective for failing to investigate or otherwise counter an issue that

never arose.

Next, Young argues his attorney should have investigated whether he qualified as

a career offender under § 4B1.1 of the Sentencing Guidelines. He argues that his prior

Missouri convictions do not meet the Guidelines’ definition of “controlled substance

offenses” because Missouri law forbids possession of positional, optical, and geometric

isomers of certain substances, while federal law embraces a narrower definition. Young’s

argument draws on cases like United States v. Ruth, 966 F.3d 642 (7th Cir. 2020), and

others, which hold that the drug offenses of some states are not predicate crimes for

§ 841’s enhanced penalties because the state statutes are categorically broader than the

federal statute by defining certain drugs (frequently cocaine) to include all isomers. Were

Young subject to a penalty enhancement in 21 U.S.C. § 841, this argument might be worth

deeper exploration (although Young’s prior convictions were for a variety of controlled

substances other than cocaine). The argument does little for Young here, however,

because his sentence was driven by the career offender provision of the Sentencing

Guidelines, not § 841.

Under the Sentencing Guidelines, an individual is a “career offender” if, among

other requirements, “the defendant has at least two prior felony convictions of either a

crime of violence or a controlled substance offense.” U.S.S.G. § 4B1.1(a) (2018 ed.). A

“controlled substance offense,” in turn, is:

[A]n offense under federal or state law, punishable by imprisonment for a

term exceeding one year, that prohibits the manufacture, import, export,

distribution, or dispensing of a controlled substance (or a counterfeit

substance) or the possession of a controlled substance (or a counterfeit

substance) with intent to manufacture, import, export, distribute, or

dispense.

Id. § 4B1.2(b). Because the definition includes no further guidance about what constitutes

a controlled substance, some courts read the provision to incorporate the Controlled

Substance Act’s definition, found in 21 U.S.C. § 802(6). Consequently, a prior state

conviction would not suffice if the state defined controlled substances more broadly than

the federal law. However, the Seventh Circuit has not adopted that approach. Instead, it

held in Ruth that the Guidelines’ definition of “controlled substance” is distinct from the

CSA’s and “is generally understood to be any of a category of behavior-altering or

addictive drugs, as heroin or cocaine, whose possession and use are restricted by law.”

966 F.3d at 654 (citation omitted). Under that view, a state conviction may qualify as a

predicate for the career offender guideline even if the state defines controlled substance

more broadly than federal law. Id.

Ruth thus forecloses Young’s argument that his Missouri offenses do not qualify

as career offender predicates. Although defendants at times have urged the court of

appeals to revisit its holding, Ruth remains good law in this circuit. See United States v.

Ramirez, 52 F.4th 705, 716 (7th Cir. 2022); United States v. Harris, No. 24-1173, 2025 WL

586834, at *2 (7th Cir. Feb. 24, 2025), cert. denied, 145 S. Ct. 2867 (2025); United States v.

Johnson, No. 22-2239, 2024 WL 3565263, at *1 (7th Cir. July 29, 2024). Young did not receive

ineffective assistance of counsel on this ground.

Finally, Young argues that his attorney was ineffective for advising him to take a

plea that contained an appeal waiver. He does not clearly explain how the inclusion of

the waiver fell below a reasonable standard of professional assistance. That omission is

problematic because “the mere existence of an appellate waiver in a plea agreement, by

itself, does not establish ineffective assistance of counsel.” Godinez v. United States, No. 23-

4418, 2025 WL 2636085, at *7 (N.D. Ill. Sept. 12, 2025); Combs v. United States, No. 19-CV-

00960-SPM, 2021 WL 2948812, at *3 (S.D. Ill. July 14, 2021). To the contrary, many courts

recognize that such waivers can be a “useful tool for obtaining concessions from the

government” through the plea negotiation process. Godinez, 2025 WL 2636085, at *7;

United States v. Carvajal-Mora, No. 08-0059, 2009 WL 5171822, at *8 (N.D. Okla. Dec. 21,

2009) (“[C]counsel is not automatically ineffective for advising a client to accept a plea

agreement with an appellate and post-conviction waiver, as appellate waivers serve a

useful purpose and are an important part of a criminal defendant’s bargain with the

government.”); see also United States v. Wenger, 58 F.3d 280, 282 (7th Cir. 1995)

(“[A] defendant inclined against appeal or willing to forgo it—perhaps to put an

unpleasant episode behind him more quickly—may obtain a concession from the

prosecutor.”). One may question in the abstract whether plea waivers are, in fact, an

effective bargaining chip for defendants given the ubiquity of their use in Rule 11

agreements, but that matter can be put aside here in light of the clear absence of any

prejudice to Young caused by the waiver or the plea agreement as a whole. As discussed

above, the Court reviewed the provision with Young at his change of plea hearing, and

he represented that he understood the extent of the rights he was waiving. Cf. Meadows

v. United States, No. 24-1052, 2025 WL 815612, at *4 (E.D. Wis. Mar. 14, 2025) (refusing to

find ineffective assistance in connection with an appeal waiver where the petitioner

merely “assert[ed] baldly” that he would have proceeded to trial had the appellate waiver

been explained to him); see also United States v. McMaster, No. 12-172, 2016 WL 11786302,

at *7 (D.N.D. Aug. 31, 2016). In fact, the plea agreement inured to his benefit because the

government agreed to an additional one-point reduction to his offense level under

U.S.S.G. § 3E1.1. (Young, supra, Doc. 123, p. 4). It also is a notable indication Young was

not prejudiced that he never attempted to bring an appeal notwithstanding the waiver.

In any event, the only issues Young says he wished to raise on appeal—his career

offender designation and his (nonexistent) enhanced penalty under § 841—are meritless

for the reasons discussed previously. See United States v. Watts, No. 14-20118, 2019 WL

1299700, at *6 (D. Kan. Mar. 21, 2019) (finding no prejudice associated with an appeal

waiver where there “were simply no sentencing issues that could have been litigated on

appeal”). Young has not established an entitlement to relief on this claim.

CONCLUSION

Young’s claims are procedurally barred because they are untimely, and he has not

established an entitlement to equitable tolling. Even if the claims were timely, they would

fail on the merits. For the reasons stated above, his motion to vacate, set aside, or correct

his sentence (Doc. 1) pursuant to 28 U.S.C. § 2255 is DENIED. This civil action is

DISMISSED with prejudice, and the Clerk of Court is DIRECTED to enter judgment

accordingly.

CERTIFICATE OF APPEALABILITY

Rule 11(a) of the Rules Governing Section 2255 Proceedings requires district courts

to consider whether to issue or deny a certificate of appealability when entering a final

order adverse to a petitioner. Under 28 U.S.C. § 2253(c)(2), a certificate of appealability

may be issued “only if the applicant has made a substantial showing of the denial of a

constitutional right.” To meet this standard, a petitioner “must have a constitutional

claim (or an underlying procedural argument on which a constitutional claim depends),

and he must ‘demonstrate that reasonable jurists would find the district court’s

assessment of his constitutional claims debatable or wrong.’” United States v. Fleming, 676

F.3d 621, 625 (7th Cir. 2012) (quoting Tennard v. Dretke, 542 U.S. 274, 282 (2004)) (emphasis

omitted); see also Slack v. McDaniel, 529 U.S. 473, 484 (2000) (holding that to obtain a

certificate of appealability after dismissal on procedural grounds, a petitioner must show

that reasonable jurists “would find it debatable whether the petition states a valid claim

of the denial of a constitutional right” and “whether the district court was correct in its

procedural ruling”).

Here, reasonable jurists would not debate that Young’s claims are procedurally

barred as untimely and are meritless, in any event. Accordingly, a certificate of

appealability is denied.

NOTICE OF APPELLATE RIGHTS

If Young wishes to contest this Order, he has two options. He may seek review of

the Order by the Seventh Circuit or request the undersigned to reconsider the Order

before going to the Seventh Circuit. If Young chooses to go straight to the Seventh Circuit,

he will only be allowed to proceed on his appeal if he first obtains a certificate of

appealability. The undersigned Chief District Judge has already declined to issue a

certificate of appealability. So, Young must request a certificate of appealability from the

Court of Appeals pursuant to Rule 22 of the Federal Rules of Appellate Procedure and

28 U.S.C. § 2253(c). He must also file a notice of appeal within 30 days from the entry of

judgment or order appealed from. Fed. R. App. P. 4(a)(1)(A). The deadline can be

extended for a short time only if Young files a motion showing excusable neglect or good

cause for missing the deadline and asking for an extension of time. Fed. R. App. P.

4(a)(5)(A), (C); see also Sherman v. Quinn, 668 F.3d 421, 424 (7th Cir. 2012) (explaining the

good cause and excusable neglect standards); Abuelyaman v. Illinois State Univ., 667 F.3d

800, 807-08 (7th Cir. 2011) (explaining the excusable neglect standard).

The current cost of filing an appeal with the Seventh Circuit is $605.00. The filing

fee is due at the time the notice of appeal is filed. Fed. R. App. P. 3(e). If Young cannot

afford to pay the entire filing fee up front, he must file a motion for leave to appeal in

forma pauperis (“IFP motion”) along with a recent statement for his prison trust fund

account. See Fed. R. App. P. 24(a)(1)(C). The IFP motion must set forth the issues Young

plans to present on appeal. See Fed. R. App. P. 24(a)(1)(C). If he is allowed to proceed IFP

on appeal, he will be assessed an initial partial filing fee. 28 U.S.C. § 1915(b)(1). He will

then be required to make monthly payments until the entire filing fee is paid. 28 U.S.C.

§ 1915(b)(2).

On the other hand, if Young wants to start with the undersigned, he should file a

motion to alter or amend the judgment under Federal Rule of Civil Procedure 59(e). The

motion must be filed within 28 days of the entry of judgment, and the deadline cannot be

extended. Fed. R. Civ. P. 59(e); 6(b)(2). The motion also must comply with Rule 7(b)(1)

and state with sufficient particularity the reason(s) that the Court should reconsider the

judgment. Elustra v. Mineo, 595 F.3d 699, 707-08 (7th Cir. 2010); see also Blue v. Hartford Life

& Acc. Ins. Co., 698 F.3d 587, 598 (7th Cir. 2012) (“To prevail on a Rule 59(e) motion to

amend judgment, a party must clearly establish (1) that the court committed a manifest

error of law or fact, or (2) that newly discovered evidence precluded entry of judgment.”)

(citation and internal quotation marks omitted).

So long as the Rule 59(e) motion is in proper form and timely submitted, the 30-

day clock for filing a notice of appeal will be stopped. Fed. R. App. P. 4(a)(4). The clock

will start anew once the undersigned rules on the Rule 59(e) motion. Fed. R. App. P.

4(a)(1)(A), (a)(4), & (a)(4)(B)(ii). To be clear, if the Rule 59(e) motion is filed outside the

28-day window or “completely devoid of substance,” the motion will not stop the clock

for filing a notice of appeal; it will expire 30 days from the entry of judgment. Carlson v.

CSX Transp., Inc., 758 F.3d 819, 826 (7th Cir. 2014); Martinez v. Trainor, 556 F.2d 818, 819-

20 (7th Cir. 1977). Again, this deadline can be extended only on a written motion by

Young showing excusable neglect or good cause.

IT IS SO ORDERED.

DATED: December 3, 2025 Tl

neff

NANCY J. ROSENSTENGEL |

Chief U.S. District Judge

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