Massengill v. United States of America

Filing 20

ORDER DENYING IN PART MOVANT'S MOTION TO VACATE, SET ASIDE, OR CORRECT SENTENCE PURSUANT TO 28 U.S.C. § 2255 ORDER DIRECTING THE CLERK TO SEND FORMS ORDER OF REFERENCE TO DETERMINE ELIGIBILITY FOR APPOINTMENT OF COUNSEL. Signed by Judge S. Thomas Anderson on 8/28/2024. (gkp)

IN THE UNITED STATES DISTRICT COURT
FOR THE WESTERN DISTRICT OF TENNESSEE
EASTERN DIVISION
______________________________________________________________________________
LAMON TERRILL MASSENGILL,

)
)
Movant,
)
v.
)
No. 1:23-cv-01037-STA-jay
)
UNITED STATES OF AMERICA,
)
)
Respondent.
)
______________________________________________________________________________
ORDER DENYING IN PART MOVANT’S MOTION TO VACATE, SET ASIDE, OR
CORRECT SENTENCE PURSUANT TO 28 U.S.C. § 2255
ORDER DIRECTING THE CLERK TO SEND FORMS
ORDER OF REFERENCE TO DETERMINE ELIGIBILITY FOR APPOINTMENT OF
COUNSEL
______________________________________________________________________________
Before the Court is Movant Lamon Terrill Massengill’s Motion to Vacate, Set Aside, or
Correct Sentence Pursuant to 28 U.S.C. § 2255 (ECF No. 1). Massengill, who is representing
himself, is an inmate, Bureau of Prisons register number 40138-509, currently housed at the
Federal Correctional Institution in Texarkana, Texas. The United States of America has responded
in opposition to Massengill’s request, and Massengill has filed a reply brief. For the reasons set
forth below, the Motion is DENIED in part. Because an evidentiary hearing will be necessary to
decide Massengill’s remaining claim, the Court will refer to the United States Magistrate Judge
the question of whether Massengill qualifies for appointment of counsel to represent him at the
evidentiary hearing and, if so, the appointment of counsel.
BACKGROUND
On April 12, 2021, a grand jury returned an indictment (no. 1:21-cr-10025, ECF No. 1),
charging Massengill with three offenses. Count 1 charged Massengill with possessing with the

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intent to manufacture, distribute, or dispense cocaine base in violation of 21 U.S.C. § 841(a)(1).
Count 2 and Count 3 charged Massengill with being a person previously convicted of a felony
offense found in possession of two different firearms, each a violation of 18 U.S.C. § 922(g)(1).
Massengill was brought before the Magistrate Judge for an initial appearance on the charges on
April 16, 2021. At the conclusion of the initial appearance, the Magistrate Judge appointed CJA
panel member Jennifer Free, Esq. to represent Massengill. Ms. Free represented Massengill
throughout the proceedings on his criminal charges. The Magistrate Judge held a detention hearing
and arraignment on April 29, 2021, at which time Massengill entered a plea of not guilty to the
charges.
After the entry of a scheduling order to govern the pretrial phase of the case, on November
24, 2021, the parties notified the Court that they had reached a plea bargain to resolve the charges
against Massengill. Massengill had agreed to plead guilty to the controlled substances offense
charged in Count 1 and the firearms offense charged in Count 2. In exchange the government
agreed to dismiss the remaining firearms count at sentencing. As part of the plea bargain,
Massengill waived his right to appeal, unless his sentence exceeded the statutory maximum. Plea
Agr. ¶ 6 (no. 1:21-cr-10025, ECF No. 27). Massengill also waived his right to bring a collateral
challenge to his sentence under 28 U.S.C. § 2255. Id. ¶ 7.
The Court held a hearing on December 13, 2021, to determine whether to accept
Massengill’s change of plea. During the plea hearing, the undersigned conducted a Rule 11
colloquy, making certain that Massengill understood the charges to which he was pleading guilty,
the minimum and maximum penalties, the rights he was giving up by pleading guilty, and the
procedure for the sentencing phase. The Assistant United States Attorney also reviewed the factual
basis for the charges against Massengill, facts which Massengill admitted in open court. Having

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satisfied itself that Massengill understood his rights and had voluntarily agreed to waive them as
part of his agreement with the government, the Court accepted Massengill’s guilty plea as to
Counts 1 and 2.
In anticipation of sentencing, the United States Probation Office prepared the presentence
report (the “PSR”) (no. 1:21-cr-10025, ECF No. 30). According to the PSR, the statutory
maximum sentence for Massengill’s drug crime was 20 years’ imprisonment. Because Massengill
qualified as an armed career criminal under the Armed Career Criminal Act, the statutory
minimum on the firearms offense was 15 years and the maximum life in prison. The PSR
calculated a total adjusted offense level of 31 and a criminal history category of VI. Id. at ¶ 27.
Based on an offense level of 31 and a criminal history category of VI, the Guidelines range for
Massengill’s offenses was 188 months to 235 months. Massengill through appointed counsel Ms.
Free filed a position paper on the PSR, stating that Massengill had no objection to the PSR. Def.’s
Position Paper, Mar. 14, 2022 (ECF No. 32).
The Court held a sentencing hearing on March 15, 2022. After hearing argument from
counsel and allocution from Massengill, the Court adopted the findings of the PSR and analyzed
the sentencing factors set forth in 18 U.S.C. § 3553(a). 1 The Court sentenced Massengill to 180

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Pursuant to 18 U.S.C. § 3553(a), a court must reach an appropriate sentence by
considering “the kinds of sentence and the sentencing range” under the advisory Guidelines and
“policy statements,” as well as the following additional factors: “the nature and circumstances of
the offense and the history and characteristics of the defendant; ... the need for the sentence
imposed . . . to reflect the seriousness of the offense, to promote respect for the law, and to provide
just punishment for the offense[,] . . . to afford adequate deterrence to criminal conduct[,] . . . to
protect the public from further crimes of the defendant[,] and . . . to provide the defendant with
needed educational or vocational training, medical care, or other correctional treatment in the most
effective manner; . . . the kinds of sentences available; . . . the need to avoid unwarranted sentence
disparities among defendants with similar records who have been found guilty of similar conduct;
and . . . the need to provide restitution to any victims of the offense.” 18 U.S.C. § 3553(a).
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months on each count to run concurrently and three years of supervised release. Judgment (no.
1:21-cr-10025, ECF No. 34) was entered the same day. Massengill did not appeal.
Massengill raises three different grounds for relief as part of his § 2255 Motion. Ground 1
alleges that Massengill’s trial counsel was ineffective for failing to file a notice of appeal when
instructed to do so and to consult with Massengill about an appeal. Massengill alleges he disagreed
with the Court’s decision to classify him as an armed career criminal and wanted to appeal that
aspect of his sentence. Massengill claims he asked Ms. Free to appeal the judgment of the Court
and that her failure to appeal violated his right to effective assistance of counsel. Ground 2 is that
trial counsel was ineffective by failing to advise Massengill he would be subject to the ACCA
enhancement. In deciding to accept a plea bargain, Massengill believed he was facing no more
than six years’ incarceration, and perhaps a sentence as short as two years. Ground 3 is that trial
counsel failed to object when the Court found Massengill’s prior convictions under Tennessee law
for aggravated assault and aggravated burglary qualified as ACCA predicate offenses. According
to Massengill, his convictions are not qualifying convictions based on the Supreme Court’s
decision in Borden v. United States, 593 U.S. 420 (2021).
The government has responded in opposition to Massengill’s § 2255 Motion. As part of
its Answer (ECF No. 16) to the § 2255 Motion, the government has submitted a transcript of
Massengill’s change-of-plea hearing (ECF No. 16-1) and a declaration from Jennifer D. Free (ECF
No. 16-2). Ms. Free states in her affidavit that as part of her representation of Massengill, she
reviewed the plea agreement with Massengill prior to the change-of-plea hearing. Consistent with
her general practice in every case, Ms. Free read the plea agreement aloud in its entirety with
Massengill and ensured he understood the terms and conditions contained in the agreement before

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he accepted it. Ms. Free explained to Massengill that the agreement did not provide for a specific
sentence and that he faced a mandatory minimum sentence of 15 years.
Ms. Free also states that she met with Massengill and his spouse before sentencing and
read through every word of the PSR with Massengill. Massengill had met with prosecutors to
discuss cooperating in other investigations; however, Massengill ultimately decided not to
cooperate when his wife expressed a concern about him doing so.

Ms. Free opines that

Massengill’s sentence would have likely been lower, had he provided assistance to the
government. Ms. Free states that any statement she might have made to Massengill about his
possible sentence assumed his cooperation with authorities.
Ms. Free finally states that she discussed with Massengill his prior convictions for burglary,
aggravated burglary, and aggravated assault. Based on his prior convictions, Ms. Free advised
Massengill before he accepted the plea bargain that he would be considered an Armed Career
Criminal offender and would face a mandatory minimum sentence of 15 years on the firearms
charge against him. Ms. Free once more advised Massengill that he would qualify as an Armed
Career Criminal offender once she reviewed the PSR with Massengill. Ms. Free denies that
Massengill or anyone else indicated to her that Massengill wanted to appeal. Ms. Free states that
Massengill and his wife left the courtroom immediately after the conclusion of the sentencing
hearing.
The government has also made copies of several of Massengill’s previous convictions
exhibits to its response. Massengill was charged with a string of burglaries from 1996 and 1997
in Chester County, Tennessee. According to the exhibits filed by the government, Massengill
ultimately pleaded guilty to the relevant charges. The Circuit Court for Chester County, Tennessee
entered separate judgments as to each charge on December 17, 1997. In an indictment dated March

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3, 1997, and docketed as State v. Lamon Massengill, case no. 3637 (ECF No. 16-3), a grand jury
in Chester County, Tennessee charged Massengill with two counts of aggravated burglary and two
counts of theft of property over $1,000, based on the robbery of two different houses committed
in June 1996. The court sentenced Massengill to four years’ imprisonment as to each of the
aggravated burglary charges and three years on the theft of property charges, each sentence to run
concurrently.
In an indictment dated July 7, 1997, and docketed as State v. Lamon Massengill, case no.
3665 (ECF No. 16-4), a Chester County grand jury charged Massengill with committing
aggravated burglary and theft of property over $500 on March 26, 1997. The court sentenced
Massengill to four years on the aggravated burglary and two years on the theft of property, both
sentences to run concurrently to each other and consecutively to Massengill’s sentence in case no.
3637.
In an indictment dated November 3, 1997, and docketed as State v. Lamon Massengill, case
no. 3683 (ECF No. 16-5), a Chester County grand jury charged Massengill with burglary, theft of
property, and vandalism, all committed on June 27, 1997. The court sentenced Massengill to four
years on the burglary and two years on the theft of property, both sentences to run concurrently to
each other and consecutively to Massengill’s sentence in case no. 3637. The government’s exhibit
does not show what the disposition of the vandalism charge was.
Finally, in an information dated November 19, 1997, and docketed as State v. Lamon
Massengill, case no. 3692 (ECF No. 16-6), the State of Tennessee charged Massengill with two
counts of aggravated burglary, one count of theft of property over $1,000, and one count of theft
of property over $500, all based on the robbery of two different houses, one in May 1996 and the
other in June 1996. The court sentenced Massengill to four years on the aggravated burglaries,

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three years on the theft of property over $1,000, and two years on the theft of property over $500,
all sentences to run concurrently to each other and with Massengill’s sentence in case no. 3637
and consecutive to his sentences in the other cases.
In its last exhibit, the government made copies of Massengill’s previous conviction for
aggravated assault part of the record. In an indictment dated September 30, 2002, and docketed
as State v. Lamon Massengill, case no. 02-612 (ECF No. 16-7), a Madison County, Tennessee
grand jury charged Massengill with two counts of attempted second degree murder and two counts
of aggravated assault on July 7, 2002. The record shows that Massengill pleaded guilty to the
aggravated assault charges and received sentences of 10 years’ incarceration on each charge.
STANDARD OF REVIEW
A petitioner seeking § 2255 relief “must allege one of three bases as a threshold standard:
(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 entire proceeding invalid.” Gabrion
v. United States, 43 F.4th 569, 578 (6th Cir. 2022) (citation omitted). A movant has the burden of
proving that he is entitled to relief by a preponderance of the evidence. United States v. Brown,
957 F.3d 679, 690 (6th Cir. 2020). “[C]onclusory allegations alone, without supporting factual
averments, are insufficient to state a valid claim under § 2255.” Gabrion, 43 F.4th at 578 (citation
omitted)).
The Sixth Amendment guarantees criminal defendants “the right . . . to have the Assistance
of Counsel for [their] defence.” U.S. Const. am. VI. The right to counsel includes “the right to
the effective assistance of counsel.” Garza v. Idaho, 586 U.S. 232, 237 (2019) (quoting Strickland
v. Washington, 466 U.S. 668, 686 (1984)). The Supreme Court has described the right to effective
assistance of counsel as “a bedrock principle” and the “foundation for our adversary system” of

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criminal justice. Martinez v. Ryan, 566 U.S. 1, 12 (2012). “[T]he Sixth Amendment’s requirement
that defendants receive ‘the effective assistance of competent counsel’ extends to all critical stages
of a criminal proceeding.” Gilbert v. United States, 64 F.4th 763, 770 (6th Cir. 2023) (quoting
Byrd v. Skipper, 940 F.3d 248, 255 (6th Cir. 2019)). A claim that an attorney’s ineffective
assistance has deprived a criminal defendant of his Sixth Amendment right to counsel is cognizable
under § 2255. Gilbert, 64 F.4th at 770 (citing Massaro v. United States, 538 U.S. 500, 504, 508–
09 (2003)). A court may only grant relief under § 2255 if the petitioner demonstrates “a
fundamental defect which inherently results in a complete miscarriage of justice.” Griffin v. United
States, 330 F.3d 733, 736 (6th Cir. 2003) (quoting Davis v. United States, 417 U.S. 333, 346
(1974)).
In order to carry his burden and show that he was deprived of his right to counsel,
Massengill “must show deficient performance by counsel and resulting prejudice to the
defendant.” Griffin, 330 F.3d at 736 (citing Strickland, 466 U.S.at 687, 694). First, to demonstrate
deficient performance, Massengill “must identify the acts or omissions of counsel that are alleged
not to have been the result of reasonable professional judgment.” Strickland, 466 at 690. “The
benchmark for judging any claim of ineffectiveness must be whether counsel’s conduct so
undermined the proper functioning of the adversarial process that the trial cannot be relied on as
having produced a just result.” Id. at 686. A court considering a claim of ineffective assistance
must apply “a strong presumption” that the attorney’s representation was “within the wide range
of reasonable professional assistance; that is, the defendant must overcome the presumption that,
under the circumstances, the challenged action might be considered sound trial strategy.” Id. at
689 (internal quotation marks omitted).

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Then, to demonstrate prejudice, a petitioner must establish “a reasonable probability that,
but for counsel’s unprofessional errors, the result of the proceeding would have been different.”
Id. at 694. “A reasonable probability is a probability sufficient to undermine confidence in the
outcome.” Id. “It is not enough ‘to show that the errors had some conceivable effect on the
outcome of the proceeding.’” Harrington v. Richter, 562 U.S. 86, 104 (2011) (quoting Strickland,
466 U.S. at 693) (citations omitted). Instead, “[c]ounsel’s errors must be ‘so serious as to deprive
the defendant of a fair trial, a trial whose result is reliable.’” Id. (quoting Strickland, 466 U.S. at
687).
Section 2255 indicates: “Unless the motion and the files and records of the case
conclusively show that the prisoner is entitled to no relief, the court shall . . . grant a prompt hearing
thereon[.]” 28 U.S.C. § 2255(b); see also Rules Governing § 2255 Proceedings, Rule 4(b). The
Sixth Circuit has “interpreted this statutory language (and the accompanying procedural rules) to
require a hearing only if a prisoner meets a standard analogous to the summary-judgment test by
creating a legitimate dispute over a legally important fact.” Wallace v. United States, 43 F.4th
595, 606–07 (6th Cir. 2022) (citations omitted). “[N]o hearing is required,” however, “if the
petitioner’s allegations cannot be accepted as true because they are contradicted by the record,
inherently incredible, or conclusions rather than statements of fact.” Monea v. United States, 914
F.3d 414, 422 (6th Cir. 2019) (quoting Valentine v. United States, 488 F.3d 325, 333 (6th Cir.
2007)).
ANALYSIS
I. Ground 1 – Counsel’s Failure to File a Notice of Appeal
In his first ground for relief, Massengill alleges that Ms. Free provided ineffective
assistance when she did not follow Massengill’s instructions to appeal the Court’s judgment.

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Massengill asserts that Ms. Free had advised him prior to sentencing that he would likely receive
a sentence of no more than 6 years’ incarceration. When the Court sentenced him to 180 months,
Massengill claims he told Ms. Free he wanted to appeal. Massengill argues that he can introduce
proof in support of his claim at an evidentiary hearing, including testimony from his wife, phone
records, and correspondence with Ms. Free. In her affidavit, Ms. Free denies that Massengill (or
his wife) ever discussed filing an appeal with her or notified her of Massengill’s wish to appeal.
The Supreme Court has held that an attorney provides ineffective assistance “if, after
consulting with his client, he disregards specific instructions from his client to file a notice of
appeal”—“a purely ministerial task.” Pola v. United States, 778 F.3d 525, 533 (6th Cir. 2015)
(quoting Roe v. Flores–Ortega, 528 U.S. 470, 477 (2000)). If a § 2255 movant can show that his
trial counsel failed to appeal “either after the client’s express instructions or because there is no
reasonable strategic reason not to appeal, then the defendant was prejudiced because he has been
deprived of the appellate proceeding altogether if there is a reasonable probability that, but for
counsel’s deficient failure to consult with him about an appeal, he would have timely appealed.”
Id. (citing Roe, 528 U.S. at 483–84).
“In reviewing a § 2255 motion in which a factual dispute arises, the habeas court must hold
an evidentiary hearing to determine the truth of the petitioner’s claims.” Valentine, 488 F.3d at
333 (internal quotation marks omitted). The Court is unable to resolve on the present record
Massengill’s claim of ineffective assistance of counsel related to an appeal in his criminal case.
The most efficient means of resolving the issues presented is through an evidentiary hearing on
Massengill’s claim that his attorney rendered ineffective assistance as it relates to his appeal.
Before setting the evidentiary hearing, the Court must next decide whether Massengill qualifies
for appointment of counsel.

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“If an evidentiary hearing is warranted, the judge must appoint an attorney to represent a
moving party who qualifies to have counsel appointed under 18 U.S.C. § 3006A.” Rule 8(c), Rules
Governing Section 2255 Proceedings for the United States District Courts (“§ 2255 Rules”).
Although Massengill may be entitled to appointed counsel, the Court presently has no information
to determine his financial eligibility. Therefore, Massengill is ORDERED to file an in forma
pauperis affidavit within thirty (30) days of the entry of this Order to demonstrate his financial
eligibility for appointment of counsel. The Clerk is DIRECTED to send Massengill the proper
forms for seeking leave to proceed in forma pauperis and make an entry on the docket stating
when those forms were mailed. The Court hereby refers to the United States Magistrate Judge the
issue of whether Massengill is financially eligible for appointed counsel and, if so, to make the
appointment. The Court will set the evidentiary hearing by separate order after the Magistrate
Judge has resolved the matter of appointment of counsel.
II. Grounds 2 & 3 – Massengill’s Waiver of his Right to File a Collateral Attack
The next issue presented is whether Massengill has made a valid waiver of his right to file
a § 2255 Motion. In his plea agreement with the government, Massengill agreed “to waive his
right to challenge his conviction and sentence, and the manner in which the sentence was
determined, and (in any case in which the term of imprisonment and fine are within maximums
provided by statute) his attorney’s alleged failure or refusal to file a notice of appeal, in any
collateral attack or future challenge, including but not limited to a motion brought under Title 28,
United States Code § 2255.” Plea Agr. ¶ 7 (no. 1:21-cr-10025, ECF No. 27). The government
argues that the collateral attack waiver in the plea agreement precludes the claims alleged in
Grounds 2 and 3. In Ground 2 of his § 2255 Motion, Massengill alleges that Ms. Free was
ineffective because she never advised him during plea negotiations he would be subject to an

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enhanced sentence under the ACCA. In Ground 3, Massengill alleges that Ms. Free failed to object
at sentencing when the Court found that Massengill’s prior convictions under Tennessee law for
aggravated assault and aggravated burglary qualified as ACCA predicate offenses.
A defendant may bargain away a right, “even a constitutional one,” as part of a plea
agreement, as long as he does so knowingly and voluntarily. Portis v. United States, 33 F.4th 331,
334–35 (6th Cir. 2022) (citing Brady v. United States, 397 U.S. 742, 748 (1970)). The same
reasoning permits a defendant to “waive his right to bring future postconviction challenges, which
are not constitutionally required, so long as the waiver is knowing and voluntary.” Id. at 335
(citing Watson v. United States, 165 F.3d 486, 489 (6th Cir. 1999)). Here, Massengill has not
alleged that he did not knowingly and voluntarily enter into the collateral attack waiver or that Ms.
Free provided ineffective assistance in negotiating a plea agreement with such a waiver. In fact,
Massengill has not addressed the collateral attack waiver or the government’s waiver argument at
all. As a result, Massengill has not properly challenged the enforceability of the plea agreement’s
collateral attack waiver.
And the record belies any such notion that Massengill did not knowingly and voluntarily
enter into the plea agreement. Federal Rule of Criminal Procedure 11 governs plea bargaining and
requires a district court “before the court accepts a plea of guilty . . . [to] address the defendant
personally in open court” and as part of the address or colloquy, to “inform the defendant of, and
determine that the defendant understands” his trial-related rights and the consequences of waiving
them by entering into a guilty plea. Fed. R. Crim. P. 11(b)(2). The Court also has a duty to
“determine that the plea is voluntary and did not result from force, threats, or promises (other than
promises in a plea agreement)” and “that there is a factual basis for the plea.” Fed. R. Crim. P.
11(b)(2) & (3).

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At a change-of-plea hearing on December 13, 2021, the Court conducted a full Rule 11
plea colloquy with Massengill. Massengill affirmed under oath that he had discussed his case with
Ms. Free and was satisfied with her representation. Plea Hr’g Tr. 13:22-14:12. Massengill stated
to the Court that he had signed the plea agreement (id. at 21:21-24), that he had gone over the
agreement with Ms. Free prior to signing it (id. at 21:2-5), and that he understood the terms of the
agreement (id. at 21:6-10). After the Assistant United States Attorney read the plea agreement
aloud, Massengill stated that the terms and conditions read aloud were the terms and conditions as
he understood them. Id. at 31:6-12. The Court then reviewed several provisions of the plea
agreement in more detail with Massengill, including the collateral attack waiver. After the Court
explained the waiver to Massengill, Massengill affirmed that he understood the waiver and that he
intended to give up his right to mount a collateral attack on his sentence. Id. at 33:21-34:15.
Massengill also represented to the Court that he was satisfied with Ms. Free’s representation and
that he had accepted the agreement freely and voluntarily. Id. at 35:6-36:15.
A defendant’s response in open court and as part of a Rule 11 plea colloquy “must prevail
over the assertions in [a] § 2255 motion.” Roman v. United States, 2021 WL 8055773, at *2 (6th
Cir. 2021) (citing Ramos v. Rogers, 170 F.3d 560, 566 (6th Cir. 1999)). “Solemn declarations in
open court carry a strong presumption of verity,” and even though “the barrier of the plea or
sentencing proceeding record, although imposing, is not invariably insurmountable,” overcoming
that presumption must nevertheless require considerable support in the record. Blackledge v.
Allison, 431 U.S. 63, 74 (1977). Massengill’s statements to the Court during the Rule 11 plea
colloquy are entitled to a presumption of truth, and Massengill has not cited anything in the record
to displace that presumption. In the absence of some showing as to why the Court should not
enforce the collateral attack waiver, the Court concludes that Massengill knowingly and

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voluntarily waived his right to challenge his conviction and sentence, and the manner in which his
sentence was determined, in a collateral attack. Massengill’s § 2255 must be denied as to Grounds
2 and 3 for this reason alone.
III. Grounds 2 & 3 – Failure on the Merits
As part of its Answer to Massengill’s § 2255 Motion, the government has gone on to argue
the merits of Massengill’s claims in Grounds 2 and 3. Even if the collateral attack waiver in the
plea agreement did not prevent Massengill from raising the claims in Grounds 2 and 3, the Court
holds in the alternative that Grounds 2 and 3 would fail on the merits.
A. Ground 2 – Ineffective Assistance in the Plea Bargaining Process
Massengill alleges in Ground 2 that Ms. Free failed to explain Massengill’s possible
sentence as an Armed Career Criminal offender during plea negotiations.

“[W]hen the

Government chooses to enter into plea negotiations, the Constitution requires that defendants
receive effective assistance in navigating that crucial process.” Rodriguez-Penton v. United States,
905 F.3d 481, 489 (6th Cir. 2018) (citing Lafler v. Cooper, 566 U.S. 156, 168 (2012)). Effective
assistance includes “accurate advice regarding sentence exposure.” Id. (citations omitted). “A
criminal defendant has a right to expect at least that his attorney will . . . explain the sentencing
exposure the defendant will face as a consequence of exercising each of the options available.”
Smith v. United States, 348 F.3d 545, 553 (6th Cir. 2003). Defense counsel cannot sufficiently
explain sentencing exposure to a defendant without “completely exploring the ranges of penalties
under likely guideline scoring scenarios, given the information available to the defendant and his
lawyer at the time.” Id.
Massengill has not shown how Ms. Free’s representation in the bargaining process was
ineffective or how her supposed ineffectiveness caused him any prejudice. First, Massengill’s

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allegation about Ms. Free’s failure to advise him about a possible sentence on the firearms offense
in Count 2 as an Armed Career Criminal offender contradicts the record at his change-of-plea
hearing. The Assistant United States Attorney reviewed the possible penalties for the offenses,
including the possibility that Massengill might qualify for an enhanced sentence and mandatory
minimum under the ACCA. Massengill represented to the Court that Ms. Free had gone over his
potential sentence with him and that he understood the range of penalties. Based on Massengill’s
responses during the plea colloquy, the Court concludes that Massengill cannot now contradict the
record and assert that Ms. Free failed to discuss the sentencing process and the possibility of an
ACCA sentence, which would have included a statutory minimum sentence of 180 months, he
might receive prior to Massengill deciding to plead guilty to Count 2. Cadavid-Yepes v. United
States, 635 F. App’x 291, 299–300 (6th Cir. 2016) (“[E]ven if counsel gives a defendant erroneous
information, a defendant is not entitled to relief if the misinformation is directly refuted on the
record by the district judge during a plea colloquy.”).
Second, Massengill has not shown how any alleged failure on Ms. Free’s part prejudiced
him during plea bargaining. Even assuming Ms. Free failed to advise Massengill about the ACCA
and a mandatory minimum sentence of 15 years, Massengill must still show that Ms. Free’s
ineffectiveness resulted in prejudice. As part of this showing, Massengill must prove either that
he would have gone to trial but for counsel’s ineffectiveness or that he would have bargained for
a more favorable plea. In order to prove prejudice in the context of plea negotiations, the defendant
must show “a reasonable probability that, with proper advice, the outcome of those negotiations
would have been different.” Rodriguez-Penton, 905 F.3d at 489–90. A defendant can establish
prejudice by “showing he would have gone to trial but for the bad advice during the plea process”

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or that “had he known about the risk of adverse . . . consequences, he would have bargained for a
more favorable plea.” Gilbert, 64 F.4th at 771 (citations omitted).
Showing prejudice with proof he would have gone to trial requires a defendant to satisfy a
two-part test: (1) going to trial “would have been rational” under the circumstances of his case;
and (2) a reasonable likelihood based on “evidence contemporaneous with his plea” that the
defendant would have elected to go to trial. United States v. Singh, 95 F.4th 1028, 1033 (6th Cir.
2024) (citing Lee v. United States, 582 U.S. 357, 370 (2017)) (other citations omitted). This
showing is a “high bar” for a defendant who pleaded guilty and available only in “unusual
circumstances.” Id. at 1033–34 (quoting Lee, 582 U.S. at 368–69).
Showing prejudice with proof he would have bargained for a more favorable plea requires
a defendant to show “based on contemporaneous evidence” the following elements: (1) a
reasonable probability the defendant would have rejected the plea offer, (2) the government would
have made an offer more favorable for the defendant, (3) the defendant would have accepted the
more favorable offer, and (3) the trial court would have accepted the plea bargain. Id. at 1034
(citations omitted). This is also a “difficult standard to meet” and one “rarely” successful. Id.
Nothing in the record shows that Massengill could satisfy the high standard and make either
showing to prove his ineffective assistance claim. Massengill has not alleged or even implied that
there is contemporaneous evidence that going to trial “would have been rational” or that he would
have in fact gone to trial. Singh, 95 F.4th at 1033. Furthermore, there is no evidence the
government made more than one plea offer to Massengill or would have considered an offer for a
specific sentence. Fed. R. Crim. P. 11(c)(1)(C) (allowing the government and a defendant to
“agree that a specific sentence or sentencing range is the appropriate disposition of the case, or
that a particular provision of the Sentencing Guidelines, or policy statement, or sentencing factor

16

does or does not apply”). For all of these reasons, Massengill has not met his burden to prove that
any ineffectiveness on Ms. Free’s part prejudiced Massengill during the plea bargaining process.
Therefore, Massengill’s § 2255 Motion is DENIED as to Ground 2.
B. Ground 3 – Failure to Object to ACCA Predicate Offenses at Sentencing
Massengill’s allegation in Ground 3 implicates the Armed Career Criminal Act and the
Court’s conclusion at sentencing that Massengill’s prior aggravated assault convictions were
ACCA predicate offenses. “The ACCA requires a district court to impose a sentence of at least
fifteen years’ imprisonment on any person who violates 18 U.S.C. § 922(g) and has three previous
convictions . . . for a violent felony or a serious drug offense, or both, committed on occasions
different from one another.” United States v. Schumaker, 83 F.4th 1031, 1035 (6th Cir. 2023)
(quoting 18 U.S.C. § 924(e)(1) (internal quotation marks omitted)). The gravamen of Massengill’s
argument is that his aggravated assault convictions from 2002 are not qualifying “violent felonies.”
Massengill also alleges in a single sentence found in a memorandum of law in support of his §
2255 Motion that his “second case of Aggravate Burglary-Forgery” does not qualify as an ACCA
violent felony. Movant’s Mem. in Support 10 (ECF No. 1, Page ID 22). The record does not
actually contain any evidence that Massengill has a forgery conviction or that such a crime factored
in any way into the Court’s determination that Massengill was an ACCA offender. In any event,
according to Massengill, Ms. Free’s failure to contest the Court’s application of the ACCA was
deficient.
The Court holds that any objection to counting Massengill’s aggravated assault convictions
as ACCA predicates would have been without merit, meaning Massengill cannot show how Ms.
Free’s decision not to object constituted ineffective of assistance of counsel. First and foremost,
Massengill had three or more qualifying ACCA violent felonies based on his prior convictions for

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burglary and aggravated burglary alone.

The record shows that at the time of his illegal gun

possession, Massengill had one previous burglary conviction and 5 aggravated burglary
convictions. The Supreme Court held in United States v. Stitt, 586 U.S. 27 (2018) that aggravated
burglary under Tennessee law constituted a violent felony for purposes of the ACCA. See also
Brumbach v. United States, 929 F.3d 791, 792 (6th Cir. 2019). According to the PSR, Massengill
committed one burglary on June 27, 1997, and five aggravated burglaries, two at different locations
on June 6, 1996; two at different locations on July 6, 1996; and one on May 14, 1997. As a matter
of law, Massengill had at least three prior violent felony convictions and qualified as an Armed
Career Criminal offender, with or without his aggravated assault convictions.
Massengill’s ineffective assistance claim focuses on the nature of his aggravated assault
convictions and whether the Court correctly counted them as ACCA violent felonies. 2 It is true
the Supreme Court in Borden held that a conviction for reckless aggravated assault under
Tennessee law did not qualify as an ACCA violent felony. Tenn. Code Ann. § 39–13–102 defines
two kinds of aggravated assaults, an intentional or knowing assault and reckless assault. § 39–13–

2

Massengill does contest whether his burglary and aggravated burglary convictions
“occurred on occasions different from each other.” Wooden v. United States, 595 U.S. 360 (2022).
The ACCA requires that qualifying predicate offenses occur on “occasions different from each
other.” The determination of whether offenses happened on “occasions different” requires
consideration consider of the following factors: (1) the timing of the offenses—“offenses separated
by substantial gaps in time or significant intervening events” would not count as part of one
occasion; (2) proximity of location of the offenses— “the further away crimes take place, the less
likely they are components of the same criminal event”; and (3) “the character and relationship of
the offenses.” Schumaker, 83 F.4th at 1035 (citing Wooden, 595 U.S. at 369).
The Supreme Court recently held that the Fifth and Sixth Amendments entitle a defendant
facing an enhanced sentenced under the ACCA “to have a jury resolve ACCA’s occasions inquiry
unanimously and beyond a reasonable doubt.” Erlinger v. United States, 144 S.Ct. 1840, 1852
(2024). Nothing in Erlinger suggested that its ruling applied retroactively to cases on collateral
review. Because Massengill has not raised this issue as grounds to vacate his sentence, the Court
need not address it further.
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102(a)(1) &(2) (2002).

The indictment against Massengill accused him of two counts of

intentional aggravated assault, not reckless aggravated assault. 3 Indictment (ECF No. 16-7, Page
ID 155-56). At the time of Massengill’s aggravated assault convictions, Tennessee punished
intentional aggravated assault as a Class C felony and reckless aggravated assault as a Class D
felony. § 39–13–102(d)(1) (2002). According to the judgment sheet, Massengill pleaded guilty
to the Class C felony “aggravated assault” which underscores the fact that Massengill was guilty
of intentional aggravated assault, not reckless aggravated assault. Massengill has not shown then
why his aggravated assault conviction would not also qualify as an ACCA violent felony.
In sum, Massengill has at least three violent felonies based on his burglary and aggravated
burglary convictions alone, even without counting his convictions for aggravated assault.
Massengill simply cannot show why Ms. Free was ineffective by failing to raise an argument about
his aggravated assault convictions at sentencing or how any supposed ineffectiveness on Ms.
Free’s part changed the outcome of the sentencing phase. Therefore, Massengill’s § 2255 Motion
is DENIED as to Ground 3.
CONCLUSION
The Court holds that a factual dispute over Massengill’s intent to appeal the judgment
against him requires an evidentiary hearing. The Court will make a final determination of
Massengill’s claim in Ground 1 of his § 2255 Motion after a determination is made about appointed
counsel and an evidentiary hearing is complete. As for the claims in Grounds 2 and 3, the Court
holds that Massengill waived his right to bring a collateral attack as part of his plea agreement. In

3

Massengill’s two aggravated assault convictions arose out of an allegation that Massengill
fired a gun at his ex-girlfriend and a male companion. Schumaker, 83 F.4th at 1037 (“Binding
Sixth Circuit precedent allows district courts to consider non-elemental facts contained in Shepard
documents to determine if a defendant has committed predicate ACCA offenses on different
occasions.”).
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the alternative, the claims fail on the merits. Therefore, Massengill’s § 2255 Motion is DENIED
as to Grounds 2 and 3.
IT IS SO ORDERED.
s/ S. Thomas Anderson
S. THOMAS ANDERSON
UNITED STATES DISTRICT JUDGE
Date: August 28, 2024.

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