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UNITED STATES DISTRICT COURT 

EASTERN DISTRICT OF MICHIGAN 

SOUTHERN DIVISION 

UNITED STATES OF AMERICA, 

Plaintiff-Respondent, Case No. 15-20246-1 

 

 Honorable Nancy G. Edmunds 

v. 

 

THEODORE CHANDLER, 

Defendant-Petitioner. 

________________________________/ 

 OPINION AND ORDER DENYING DEFENDANT’S MOTION UNDER 

28 U.S.C. § 2255 TO VACATE, SET ASIDE, OR CORRECT SENTENCE [216] 

Defendant-Petitioner Theodore Chandler moves the Court, through counsel, to 

vacate, set aside, or correct his sentence under 28 U.S.C. § 2255. (ECF No. 216.) The 

government opposes the motion. (ECF No. 226.) Defendant has filed a reply. (ECF No. 

228.) For the reasons below, the Court DENIES Defendant’s § 2255 motion. 

I. Background 

On April 23, 2015, Defendant was indicted in this district with conspiracy to 

possess with intent to distribute heroin in violation of 21 U.S.C. §§ 841(a)(1) and 846. 

(ECF No. 1.) On October 28, 2015, Defendant was charged in a first superseding 

indictment with two counts—conspiracy to possess with intent to distribute controlled 

substances (one kilogram or more of heroin and 500 grams or more of cocaine) in 

violation of 21 U.S.C. §§ 841(a)(1) and 846 (Count 1) and conspiracy to launder money 

instruments in violation of 18 U.S.C. § 1956(a)(1), (h) (Count 2). (ECF No. 42.) On 

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November 8, 2016, Defendant pled guilty to both counts in the superseding indictment 

pursuant to a Rule 11 plea agreement. (ECF No. 121.) 

The drug offense in the original indictment had a mandatory minimum of ten years 

and a maximum penalty of life. (ECF No. 14.) And because Defendant had two previous 

felony drug trafficking convictions, the government could have filed an enhancement 

under 21 U.S.C. § 851 to require a life sentence.1 (ECF No. 210, PageID.1556.) In 

exchange for Defendant’s plea, the government agreed to file the superseding indictment 

charging Defendant with a lesser drug offense that had a mandatory minimum of five 

years and a maximum of forty years. The government also agreed not to file a penalty 

enhancement and “to limit the scope of Count One to cocaine (i.e., not require a plea to 

conspiracy to distribute heroin).” (ECF No. 121, PageID.640.) The plea agreement noted 

“[t]he government calculates the guideline range as set forth in the attached worksheets 

and calculates that range as life,” but that Defendant disputes application of a crossreference to the first-degree murder guideline in U.S.S.G. § 2A1.1. (Id. at PageID.644.) 

The agreement further noted “the government will recommend that the sentence be 

with[in] the guideline range the government believes applies as reflected in the attached 

worksheets,” but this recommendation would not be binding on the Court. (Id. at 

PageID.644-45.) 

After Defendant entered his guilty plea, the Court took the plea agreement under 

advisement, referred the matter to the probation department for a presentence 

investigation report (“PSR”), and scheduled the case for sentencing. (ECF No. 210, 

PageID.1566.) The probation department then prepared a PSR in which it applied a 

1 These penalties were in effect at the time—prior to passage of the First Step Act. 

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cross-reference to § 2A1.1 and found the advisory guideline range to be 360 months to 

life imprisonment but because of the statutory caps on each count, the range became 

360 to 720 months. Defendant objected to the application of the cross-reference to the 

murder guideline. (ECF No. 186.) The government had sought to enhance the sentence 

for Count 1 under this cross-reference because it believed Defendant was responsible for 

the murder of a former associate by the name of Dynasty Myles. After holding extensive 

evidentiary hearings, the Court denied the government’s request do so, finding the 

alleged murder not sufficiently related to the drug trafficking offense Defendant had pled 

guilty to. See United States v. Chandler, No. 15-20246, 2018 U.S. Dist. LEXIS 14213, at 

*23-24 (E.D. Mich. Jan. 30, 2018). 

After the Court declined to apply § 2A1.1, the probation department prepared a 

new PSR, which instead relied on the drug and money laundering guidelines in U.S.S.G. 

§ 2D1.1 and § 2S1.1 and found the guideline range to be 324 to 405 months. This PSR 

calculated the drug quantity using both cocaine and heroin and included enhancements 

for possessing a firearm, continuing criminal conduct, and leadership. It also found 

Defendant to be in criminal history category III. Defendant filed written objections to the 

revised PSR, arguing in part that the government was bound by the plea agreement to 

limit the scope of Count 1 to 1,968 grams of cocaine.2 The government filed a written 

2 The factual basis for Count 1 in the plea agreement stated that “[f]rom at least as 

early as 2012 until January 2015, [Defendant] agreed with others to obtain and sell 

controlled substances, including cocaine, and the total amount of cocaine exceeded 500 

grams” and gave as an example an incident that took place in January 2015 in which 

Defendant directed two of his co-defendants to travel from Detroit to Arizona to obtain 

cocaine and heroin; those individuals were later stopped by law enforcement officers, who 

found and seized 1,968 grams of a substance containing cocaine. (ECF No. 121, 

PageID.642.) 

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response, arguing the plea agreement was not binding on the Court and the probation 

department’s calculations were correct. (ECF No. 203.) 

The parties appeared before the Court for a sentencing hearing on June 6, 2018. 

(ECF No. 209.) Defendant, through his attorney, voiced his objections to the revised 

PSR, while the government advocated in favor of the calculations in the report. The Court 

sustained Defendant’s objection to a two-level enhancement for possession of a firearm 

but overruled his remaining objections. Based on these findings, the guideline range 

became 262 to 327 months. The parties then made their arguments regarding what they 

believed to be an appropriate sentence pursuant to the sentencing factors. Defendant 

requested a sentence of sixty months, the mandatory minimum penalty, while the 

government argued the sentence should be forty years. Ultimately, the Court granted a 

downward variance from the guideline range and sentenced Defendant to 235 months of 

imprisonment on each count, to run concurrently with each other. (ECF No. 206.) 

On appeal, Defendant raised three arguments regarding the way the Court 

calculated the guideline range. See United States v. Chandler, 764 F. App’x 502, 504-05 

(6th Cir. 2019). The Sixth Circuit affirmed Defendant’s sentence. Id. at 505. Defendant 

now brings this motion pursuant to § 2255. 

II. Standard of Review 

Under § 2255(a), “[a] prisoner in custody under sentence of a [federal] court . . . 

claiming the right to be released . . . may move the court which imposed the sentence to 

vacate, set aside or correct the sentence.” To prevail on a § 2255 motion, the petitioner 

must allege: “(1) an error of constitutional magnitude; (2) a sentence imposed outside 

the statutory limits; or (3) an error of fact or law that was so fundamental as to render the 

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entire proceeding invalid.” Mallett v. United States, 334 F.3d 491, 496-97 (6th Cir. 2003) 

(quotation marks and citation omitted); see also Anderson v. United States, 246 F. Supp. 

2d 758, 760 (E.D. Mich. 2003). 

III. Analysis 

Defendant brings two ineffective assistance of counsel claims. A defendant has a 

right to “reasonably effective assistance” of counsel. Strickland v. Washington, 466 U.S. 

668, 687 (1984). To establish an ineffective assistance of counsel claim, the defendant 

must prove both that 1) “counsel’s performance was deficient” and 2) “the deficient 

performance prejudiced the defense.” Id. The first prong “requires showing that counsel 

made errors so serious that counsel was not functioning as the counsel guaranteed the 

defendant by the Sixth Amendment,” and the second prong “requires showing that 

counsel’s errors were so serious as to deprive the defendant of a fair trial, a trial whose 

result is reliable.” Id. 

“[T]here is a strong presumption that legal counsel is competent.” United States 

v. Osterbrock, 891 F.2d 1216, 1220 (6th Cir. 1989). Because the defendant must 

overcome the presumption that the challenged action may be considered sound strategy, 

Strickland, 466 U.S. at 689, “[a] reviewing court must give a highly deferential scrutiny to 

counsel’s performance,” Ward v. United States, 995 F.2d 1317, 1321 (6thCir. 1993). “The 

reasonableness of counsel’s performance is to be evaluated from counsel’s perspective 

at the time of the alleged error and in light of all the circumstances.” Kimmelman v. 

Morrison, 477 U.S. 365, 384 (1986). “The defendant must show that there is a reasonable 

probability that, but for counsel’s unprofessional errors, the result of the proceeding would 

have been different. A reasonable probability is a probability sufficient to undermine 

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confidence in the outcome.” Strickland, 466 U.S. at 694. The defendant bears the burden 

of proving both prongs of the analysis. Id. at 687. 

A. Defendant Has Not Established Ineffective Assistance of Counsel 

Based on an Alleged Breach of the Plea Agreement. 

Defendant argues Counsel was ineffective for failing to argue the government 

breached the plea agreement both before this Court and the Sixth Circuit.3 The 

government allegedly breached the agreement by advocating for the guideline 

calculations in the PSR prepared after the Court declined to apply the murder crossreference, which differed from those in the worksheets attached to the plea agreement.4 

More specifically, the government advocated for 1) a base offense level of 32 based on 

both cocaine and heroin instead of a base level of 30 based on cocaine only, 2) two 

additional two-level enhancements, and 3) a criminal history category of III instead of II. 

The Sixth Circuit has instructed courts to “use traditional contract law principles in 

interpreting and enforcing” plea agreements because they are contractual in nature. 

United States v. Bowman, 634 F.3d 357, 360 (6th Cir. 2011) (internal quotation marks 

and citation omitted). When determining whether a plea agreement has been breached, 

courts examine what the defendant “reasonably understood” when he entered into the 

agreement. United States v. Phibbs, 999 F.2d 1053, 1081 (6th Cir. 1993). “[T]he most 

persuasive evidence of what a defendant reasonably appreciated as his bargain is found 

in the plain language of the court-approved agreement.” Id. 

3 The same attorney represented Defendant at the trial and appellate levels. 

4 According to Defendant, without the murder cross-reference, the remaining 

calculations as set forth in the worksheets would lead to a guideline range of 151-188 

months. 

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Here, the government agreed not to file a sentencing enhancement under § 851, 

not to require a plea to conspiracy to distribute heroin, and to recommend a sentence 

within “the guideline range the government believes applies as reflected in the attached 

worksheets,” which was 360 months to life. It kept all of those promises. And while the 

agreement stated “[t]he government calculates the guideline range as set forth in the 

attached worksheets,” those worksheets were premised on an application of the crossreference to the murder guideline. Indeed, the agreement went on to explicitly note in the 

same sentence that the government “calculates that range as life.” The agreement did 

not include any promises regarding the government’s position as to the guidelines if the 

Court were to decline applying the cross-reference. See United States v. Danou, 260 F. 

App’x 864, 868 (6th Cir. 2008) (“We will hold the Government to the promises it made, 

but we will not hold the Government to promises it did not make.”) Nor can the agreement 

be reasonably understood to include any such promises. Thus, the Court finds the 

government did not breach the plea agreement when it advocated in favor of the 

calculations in the revised PSR. Because there was no breach, Defendant has not shown 

that Counsel’s performance was deficient.5

5 Because a court may either order specific performance or permit a defendant to 

withdraw the plea if it finds there was a breach, see Peavy v. United States, 31 F.3d 1341, 

1346 (6th Cir. 1994), the government argues Counsel may have chosen not to make this 

argument as part of a sound strategy. More specifically, if Defendant was allowed to 

withdraw the plea, he may have had to face a mandatory life sentence and would be 

worse off. Defendant notes, however, that the Sixth Circuit has indicated that when a 

defendant seeks only specific performance to remedy a breach, a court “‘should honor 

that election.’” See United States v. Ligon, 937 F.3d 714, 721 (6th Cir. 2019) (quoting 

United States v. Warner, 820 F.3d 678, 685 (4th Cir. 2016)). In light of the Court’s finding 

that there was no breach, the Court need not resolve this issue. But the Court questions 

whether specific performance, which involves a resentencing by a different judge, see 

Santobello v. New York, 404 U.S. 257, 263 (1971), would be appropriate here where the 

alleged breach took place after a significant issue raised during sentencing—application 

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But even if Defendant could establish the first Strickland prong, he cannot show 

the any breach of the plea agreement prejudiced his defense. As the Supreme Court has 

noted, “[t]he defendant whose plea agreement has been broken by the Government will 

not always be able to show prejudice, either because he obtained the benefits 

contemplated by the deal anyway (e.g., the sentence that the prosecutor promised to 

request) or because he likely would not have obtained those benefits in any event.” 

Puckett v. United States, 556 U.S. 129, 141-42 (2009). Here, Defendant does not even 

attempt to argue the Court was swayed by the government’s breach. Instead Defendant 

relies on cases that predate Puckett, including United States v. Barnes, 278 F.3d 644, 

648 (6th Cir. 2002), to argue that whether or not the Court was influenced by the 

government’s breach is inconsequential. But the Sixth Circuit has “squarely held that ‘[it] 

do[es] not think Barnes’ holding, post-Puckett, applies.’” See United States v. Logan, 542 

F. App’x 484, 491 (6th Cir. 2013) (quoting United States v. Keller, 665 F.3d 711, 715 (6th 

Cir. 2011)). In Puckett, 556 U.S. at 133-34, the Supreme Court held that plain error 

analysis applies in “the usual fashion” to a breach of the plea agreement. So, a defendant 

who does not object to a breach before the district court must show the breach affected 

the outcome of the district court proceedings before obtaining relief on appeal. Id. at 135. 

“And because [Defendant] complains of a breached plea agreement, ‘the outcome he 

must show to have been affected is his sentence.’” See United States v. Fuentes-Majano, 

407 F. App’x 900, 903 (6th Cir. 2011) (quoting Puckett, 556 U.S. at 142 n.4). Otherwise, 

a defendant may “game the system, waiting to see if the sentence later strikes him as 

of a cross-reference to the murder guideline—had already been resolved by this Court in 

favor of Defendant. 

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satisfactory, and then seeking a second bite at the apple by raising the claim.” Puckett, 

556 U.S. at 140 (internal quotation marks and citation omitted). “The standard for 

prejudice under Strickland is virtually identical to the showing required to establish that a 

defendant’s substantial rights were affected under plain error analysis.” Becht v. United 

States, 403 F.3d 541, 549 (8th Cir. 2005); see also United States v. Dominguez Benitez, 

542 U.S. 74, 81-83 (2004). Thus, to succeed on his ineffective assistance of counsel 

claim, Defendant must show that any breach by the government affected his sentence. 

After the Court denied the government’s request to apply a cross-reference to the 

murder guideline, the probation department prepared a revised PSR. While the 

government advocated for the calculations set forth in the revised report, the Court made 

its own findings regarding those calculations, including sustaining Defendant’s objection 

to a two-level enhancement for possession of a firearm. (See ECF No. 209.) Ultimately, 

the guideline range was lower than the range in the agreement and the Court varied 

downward even further when imposing sentence. Because Defendant has not shown 

there is a reasonable probability his sentence would have differed had the government 

not advocated in favor of the calculations in the revised PSR, he has not satisfied the 

second prong of the Strickland analysis. Thus, Defendant is not entitled to relief on his 

ineffective assistance of counsel claim stemming from Counsel’s failure to argue the 

government breached the plea agreement. 

B. Defendant Has Not Established Ineffective Assistance of Counsel 

Based on Allegedly Erroneous Pre-Plea Advice. 

Defendant argues Counsel’s erroneous pre-plea advice resulted in an unknowing 

and involuntary guilty plea. In support of this claim, Defendant has submitted a 

declaration stating Counsel had informed him he would only be held accountable for 

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1,968 grams of cocaine and no amount of heroin. (ECF No. 218-1.) He further avers that 

had he known he would be held accountable for both cocaine and heroin, he would not 

have pled guilty and would have proceeded to trial instead. (Id.) 

As a general matter, a defendant may satisfy the prejudice prong of Strickland if 

he shows there is a reasonable probability that but for counsel’s errors, he would not have 

pled guilty and would have insisted on going to trial. Hill v. Lockhart, 474 U.S. 52, 60 

(1985). But a proper plea colloquy cures any prejudice stemming from a defense 

counsel’s inaccurate statements about a plea agreement. See Ramos v. Rogers, 170 

F.3d 560, 565 (6th Cir. 1999); Warner v. United States, 975 F.2d 1207, 1214 (6th Cir. 

1992). Here, Defendant himself acknowledges the Court followed standard Rule 11 

protocols. The Court specifically explained the maximum sentence Defendant could 

receive and noted it had the discretion to impose a sentence outside the guideline range. 

(ECF No. 210, PageID.1549-50, 1559.) The Court also asked Defendant if anyone had 

made any other promise or assurance to him in an effort to get him to plead guilty and he 

stated that nobody had. Id. at PageID.559; see Warner, 975 F.2d at 1212 (noting that 

where the district court has followed the required Rule 11 procedure, “the defendant is 

bound by his statements in response to the court’s inquiry”) (internal quotation marks and 

citation omitted). Thus, even if Counsel had provided erroneous pre-plea advice, 

Defendant cannot establish prejudice on this basis. Defendant is therefore not entitled to 

relief on his second ineffective assistance of counsel claim. 

IV. Request for Evidentiary Hearing 

Defendant requests the Court hold an evidentiary hearing in connection with his 

second claim. After reviewing the briefs and materials submitted by the parties and the 

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entire record in this case, the Court finds an evidentiary hearing is not needed because 

“the record conclusively shows that the petitioner is entitled to no relief.” See Valentine 

v. United States, 488 F.3d 325, 333 (6th Cir. 2007) (quotation marks and citation omitted).

V. Certificate of Appealability 

Federal Rule of Appellate Procedure 22(b) provides that a petitioner cannot take 

an appeal in § 2255 proceeding unless a certificate of appealability is issued under 28 

U.S.C. § 2253(c). Rule 11 of the Rules Governing Section 2255 Proceedings requires 

that a “district court must issue or deny a certificate of appealability when it enters a final 

order adverse to the applicant.” To receive a certificate of appealability, “a petitioner must 

show that reasonable jurists could debate whether (or, for that matter, agree that) the 

petition should have been resolved in a different manner or that the issues presented 

were adequate to deserve encouragement to proceed further.” Miller-El v. Cockrell, 537 

U.S. 322, 336 (2003) (quotation marks and citation omitted). 

Because Defendant has failed to show that reasonable jurists could debate 

whether his petition should have been resolved in a different matter, the Court denies him 

a certificate of appealability. 

VI. Conclusion 

Based upon the foregoing, IT IS ORDERED that Defendant’s motion for postconviction relief is DENIED WITH PREJUDICE. IT IS FURTHER ORDERED that a 

certificate of appealability is DENIED. 

SO ORDERED. 

 s/Nancy G. Edmunds 

 Nancy G. Edmunds 

 United States District Judge 

Dated: February 10, 2022 

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I hereby certify that a copy of the foregoing document was served upon counsel of record 

on February 10, 2022, by electronic and/or ordinary mail. 

 s/Lisa Bartlett 

 Case Manager 

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