In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 19-1257
MONTA Y. ANDERSON,
Petitioner-Appellant,
v.
UNITED STATES OF AMERICA,
Respondent-Appellee.
____________________
Appeal from the United States District Court for the
Central District of Illinois.
No. 1:17-cv-01542 — Michael M. Mihm, Judge.
____________________
ARGUED OCTOBER 29, 2020 — DECIDED NOVEMBER 23, 2020
____________________
Before FLAUM, KANNE, and HAMILTON, Circuit Judges.
FLAUM, Circuit Judge. Petitioner-appellant Monta Ander-
son pleaded guilty to conspiracy to distribute heroin. Because
he stipulated as part of his plea agreement that heroin he dis-
tributed through the conspiracy caused the death of James
Reader, the district court applied a statutory sentencing en-
hancement that mandates a minimum sentence of twenty
years’ imprisonment for a drug offense that resulted in death.
Anderson ultimately received a below-Guidelines sentence of
2 No. 19-1257
223 months’ imprisonment and ten years of supervised re-
lease. He thereafter petitioned for collateral relief under
28 U.S.C. § 2255, arguing that his counsel provided ineffective
assistance in the plea-bargaining process. The district court
denied Anderson’s § 2255 petition without an evidentiary
hearing, holding that Anderson’s counsel was not ineffective.
Based on the record and circumstances of this case, we find
that Anderson was entitled to an evidentiary hearing on his
claim of ineffective assistance of counsel. We therefore vacate
the district court’s denial of Anderson’s petition and remand
for a hearing.
I. Background
The Offense Conduct and Guilty Plea
Beginning in 2010, Anderson participated in a conspiracy
to distribute heroin in central Illinois. Over the course of two
years, he bought heroin for the conspiracy from a Chicago
supplier and distributed it in central Illinois to users and deal-
ers. One of those dealers was a man named Anthony Mansini.
On August 25, 2012, Reader, a twenty-one-year-old addict,
purchased heroin from a dealer unconnected to Anderson in
Peoria, Illinois. Reader used that heroin intravenously in the
early afternoon. Later that same day, Reader purchased an ad-
ditional half-gram of heroin from Mansini, who had obtained
it from Anderson. Reader then used that heroin and was
found dead that evening. According to the coroner’s postmor-
tem report, the cause of death was “opiate intoxication,” but
the report did not attribute Reader’s death to one heroin dose
or the other, or make any findings on the incremental effects
of other drugs. The accompanying toxicology report noted the
No. 19-1257 3
presence of heroin metabolites and Benadryl, and their re-
spective amounts, in Reader’s system when he died.
A grand jury indicted Anderson and four co-defendants
on charges of conspiracy to distribute heroin in violation of
21 U.S.C. §§ 841(a)(1), 841(b)(1)(A), and 846. Ultimately, three
of the four defendants, including Anderson, pleaded guilty.
During plea negotiations with the government, Anderson’s
counsel had access to the postmortem and toxicology reports.
Under the terms of his plea agreement, Anderson admit-
ted to distributing the heroin that resulted in Reader’s death.
The parties “agree[d] and stipulate[d] that pursuant to … Sec-
tion 841(b)(1)(A), because death and serious bodily injury re-
sulted from the use of heroin distributed by the defendant as
an overt act of this conspiracy, this count carrie[d] a manda-
tory minimum sentence of 20 years imprisonment and a max-
imum sentence of life imprisonment.” The parties further
agreed that twenty years was the appropriate sentence, and
that Anderson waived any right to appeal or collaterally at-
tack his conviction or sentence, except for an involuntariness
or ineffective-assistance-of-counsel claim.
At the change-of-plea hearing, Anderson concurred with
the plea agreement’s factual statements, but noted that they
did not capture all the details surrounding Reader’s death.
During the plea colloquy, Anderson told the district court that
he might have a factual defense to causation of Reader’s death
because Reader had bought heroin from other sources and
used prescription drugs. Nonetheless, Anderson assured the
district court that he was not disputing any part of the agree-
ment, including the stipulation regarding the cause of
Reader’s death. The district court also verified that Anderson
had discussed the charges and any possible defenses with his
4 No. 19-1257
attorney “several times” and that he was “fully satisfied” with
his counsel’s representation and advice. The district court ac-
cepted Anderson’s plea and, after crediting him for time
served in state prison for a related offense, sentenced him to
223 months’ imprisonment—rather than the life sentence
called for by § 841(b)(1)(A) and the U.S. Sentencing Guide-
lines—followed by ten years of supervised release.
Post-Judgment Proceedings
Anderson appealed the judgment against him. Anderson
first sent a letter to the district court asserting that he received
ineffective assistance of counsel in connection with his guilty
plea and asking the court to file a notice of appeal on his be-
half. After the district court docketed the appeal, Anderson’s
counsel filed another notice of appeal and moved to dismiss
Anderson’s first pro se appeal, which we granted. In the sec-
ond appeal, Anderson’s counsel filed an Anders brief and
moved to withdraw. We granted the motion to withdraw and
dismissed that appeal as well, noting that Anderson’s broad
waiver of appellate rights foreclosed appeal unless his guilty
plea was invalid. While his direct appeal was pending, An-
derson also moved to withdraw his guilty plea. The district
court denied the motion for lack of subject matter jurisdiction
during the pendency of his direct appeal, and we affirmed.
Anderson then initiated these § 2255 proceedings by filing
a pro se “Motion for Extension of Time to File Memorandum
in Support of § 2255 Motion.” Seven months later, he supple-
mented his initial motion with substantive arguments. Ander-
son alleged that his plea was “not knowing and voluntary,
because [he] received ineffective [assistance] of counsel, and
but for her errors, [he] would not have pled guilty.” Specifi-
cally, he contended that his counsel did not adequately
No. 19-1257 5
investigate the cause of Reader’s death and advise Anderson
of the “but-for” causation standard set forth in Burrage v.
United States, 571 U.S. 204, 218–19 (2014).
The district court ordered the government to respond to
Anderson’s § 2255 petition. The court also ordered his plea
counsel to submit an affidavit responding to Anderson’s inef-
fective assistance claim and describing the advice she pro-
vided regarding the “death results” enhancement and the
plea agreement. The government responded on the merits
and attached an affidavit from Anderson’s counsel. The affi-
davit stated: (1) Anderson’s counsel “made all of the govern-
ment[’]s discovery available to Mr. Anderson, including Mr.
Reader’s toxicology results”; (2) prior to Anderson’s guilty
plea, Anderson was aware of the need to hire a medical ex-
aminer “if additional interpretation of the medical reports
contained in the discovery was desired”; (3) Anderson “au-
thorized [her] to proceed with plea negotiations without hir-
ing a medical examiner”; and (4) she was “not trained to in-
terpret toxicology results” and “never discussed” the toxicol-
ogy evidence with anyone who had relevant training, and
therefore, she could not “determine the accuracy” of Ander-
son’s arguments regarding the cause of Reader’s death.
The district court denied Anderson’s § 2255 petition on the
merits without an evidentiary hearing. The court held that
“[t]he record before the Court, primarily the transcript from
[Anderson’s] Change of Plea Hearing, confirms that [he] en-
tered into his plea agreement knowingly and voluntarily, and
that his counsel was effective during plea negotiations.” The
court also concluded that Anderson’s “self-serving claim that
he was unaware of the availability of a ‘but-for’ defense is
simply not credible in light of the documentation before the
6 No. 19-1257
Court.” The district court further declined to issue a certificate
of appealability, but we granted one. This appeal followed.
II. Discussion
Anderson argues on appeal that the district court erred in
dismissing his § 2255 petition. “When reviewing the denial of
a federal prisoner’s § 2255 petition, we review the district
court’s legal conclusions de novo, its factual findings for clear
error, and its decision to forgo holding an evidentiary hearing
for abuse of discretion.” Martin v. United States, 789 F.3d 703,
705 (7th Cir. 2015). “The district court’s decision must strike
us as fundamentally wrong for an abuse of discretion to oc-
cur.” Williams v. Chi. Bd. of Educ., 155 F.3d 853, 857 (7th Cir.
1998) (per curiam) (citation and internal quotation marks
omitted).
The Government’s Timeliness Argument
There is a one-year statute of limitations for filing habeas
petitions. 28 U.S.C. § 2255(f). In relevant part, the limitation
period runs from “the date on which the judgment of convic-
tion becomes final.” Id. § 2255(f)(1). Here, Anderson’s convic-
tion became final when the ninety-day period for filing a pe-
tition for a writ of certiorari with the Supreme Court follow-
ing our affirmance on direct review expired. See Clay v. United
States, 537 U.S. 522, 532 (2003). On appeal, the government ar-
gues for the first time that Anderson’s petition is untimely un-
der § 2255(f)(1) because he did not file his motion within one
year of that date. Despite more than a year of litigation below
regarding Anderson’s § 2255 petition, the government never
raised this timeliness argument in the district court. Instead,
it moved to dismiss on the merits.
No. 19-1257 7
“We are not required to address the government’s belated
timeliness argument.” Arreola-Castillo v. United States,
889 F.3d 378, 382 (7th Cir. 2018). “The statute of limitations in
§ 2255(f)[(1)] is not a jurisdictional requirement, but rather an
affirmative defense.” Id. Ordinarily, a defendant must raise a
statute of limitations defense in its answer. Day v. McDonough,
547 U.S. 198, 207–08 (2006) (citing Fed. R. Civ. P. 8(c), 12(b),
15(a)). Failure to do so results in forfeiture of the defense. Id.
Accordingly, “courts are under no obligation to raise the time
bar sua sponte.” Id. at 205.
We nevertheless have discretion to examine—on our own
initiative—the timeliness of a habeas petition. Wood v. Mi-
lyard, 566 U.S. 463, 471, 473 (2012) (citing Day, 547 U.S. at 201).
As we have observed previously, this discretion is limited.
When the government contends, as it does here, that it “acci-
dentally forfeit[ed] a timeliness argument, our power to de-
cide an appeal on a forfeited ground should be used only in
exceptional cases.” Arreola-Castillo, 889 F.3d at 383 (citation
and internal quotation marks omitted). “For good reason, ap-
pellate courts ordinarily abstain from entertaining issues that
have not been raised and preserved in the court of first in-
stance.” Wood, 566 U.S. at 473. In addition, we must also give
“[d]ue regard for the trial court’s processes and time invest-
ment.” Id. “It typically takes a district court more time to de-
cide a habeas case on the merits, than it does to resolve a pe-
tition on threshold procedural grounds.” Id. “When a court of
appeals belatedly interjects a procedural impediment after
resolution on the merits, ‘the district court’s labor is dis-
counted.’” Arreola-Castillo, 889 F.3d at 383 (quoting Wood,
566 U.S. at 474). “Perhaps even more troubling, ‘the appellate
8 No. 19-1257
court acts not as a court of review but as one of first view.’”
Id. (quoting Wood, 566 U.S. at 474).
Here, we do not exercise our discretion to consider the
government’s timeliness argument sua sponte. We have de-
clined to exercise that discretion on at least three prior occa-
sions. See Arreola-Castillo, 889 F.3d at 383–84; Turner v. United
States, 693 F.3d 756, 758–59 (7th Cir. 2012); Hill v. Werlinger,
695 F.3d 644, 647 (7th Cir. 2012). So too here, the government
“has presented nothing to show that this is an ‘exceptional
case’ in which we should base our decision on a forfeited
ground.” Werlinger, 695 F.3d at 647 (quoting Wood, 566 U.S. at
473). Furthermore, the government does not cite any other ex-
amples of cases where we exercised our discretion to address
a forfeited timeliness argument in a habeas case on appeal.
The government asserts that the circumstances of this case
“militate in favor” of our consideration of its statute of limita-
tions defense because Anderson’s filings “may have created
confusion regarding [the] deadline for a motion to vacate.”
The government would have us hold Anderson to this dead-
line while excusing its own failure to raise the timeliness de-
fense despite almost a year between when Anderson initiated
his § 2255 proceedings and the government’s response. We
decline to penalize Anderson for failing to meet a deadline
that the government itself did not identify. In addition, the
district court presided over Anderson’s habeas petition for
over a year and ultimately resolved it on the merits. To dis-
miss the petition now on a forfeited defense would effectively
“discount” the district court’s efforts. See Arreola-Castillo,
889 F.3d at 383. Therefore, we decline to consider the govern-
ment’s forfeited timeliness defense.
No. 19-1257 9
Ineffective Assistance of Counsel
Turning to the merits, Anderson argues that his plea was
not knowing and voluntary because his lawyer was constitu-
tionally ineffective for failing to investigate the factual and le-
gal bases for applying the death results enhancement of
§ 841(b)(1)(A) to his sentence.
The Sixth Amendment guarantees a criminal defendant
the effective assistance of competent counsel during the plea-
bargaining process. Lafler v. Cooper, 566 U.S. 156, 162 (2012).
To prevail on his ineffective assistance claim, Anderson must
satisfy the two-pronged test of Strickland v. Washington,
466 U.S. 668 (1984). First, Anderson must show that his coun-
sel’s performance was deficient, which requires him to estab-
lish that his “counsel’s representation fell below an objective
standard of reasonableness” when measured against “pre-
vailing professional norms.” Id. at 688. Second, Anderson
must show that this deficient performance prejudiced his de-
fense. Id. at 687. To establish prejudice in the plea-bargaining
context, Anderson must demonstrate a reasonable probability
that “the outcome of the plea process would have been differ-
ent with competent advice.” Lafler, 566 U.S. at 163.
1. Deficient Performance
Anderson argues that his counsel performed deficiently in
two ways. First, he contends that his counsel “fail[ed] to in-
vestigate the factual basis for the ‘death results’ enhance-
ment.” He specifically alleged in his petition that his counsel
should have consulted an expert regarding Reader’s toxicology
report and determined whether the government could prove
beyond a reasonable doubt that heroin supplied by Anderson
was the but-for cause of Reader’s death. Second, Anderson
10 No. 19-1257
alleged that his counsel “fail[ed] to advise him on the viability
of a but-for causation defense to the [death results] enhance-
ment.”
Anderson has alleged facts sufficient to support his claim
of deficient performance. Under the standard set forth in Bur-
rage v. United States, 571 U.S. 204 (2014), the government was
required to prove that heroin distributed by Anderson was a
“but-for,” or at least an “independently sufficient,” cause of
Reader’s death for the sentencing enhancement of
§ 841(b)(1)(A) to apply, id. at 218–19. The evidence did not
clearly show, however, that Anderson’s heroin was the but-
for cause of death. Reader ingested two heroin doses the day
he died; only one came from Anderson. The postmortem re-
port listed Reader’s cause of death only as “opiate intoxica-
tion” without explaining whether the heroin from Anderson
was independently sufficient to cause death. Furthermore,
while the exact times are unknown, the record indicates that
Reader could have injected the two heroin doses and subse-
quently overdosed within the space of only a few hours.1
Even without Anderson’s heroin, therefore, the first dose of
heroin alone, or perhaps in interaction with the Benadryl also
in Reader’s system, may have been independently sufficient
to result in death. See, e.g., United States v. Harden, 893 F.3d
434, 440 (7th Cir. 2018) (expert testified in case involving
death results enhancement that someone could die “‘within
some hours’ after injecting heroin, depending on the potency
of the drug”). Adequate investigation of the toxicology results
1In his opening brief, Anderson asserts that a maximum of three hours
passed between Reader’s first heroin injection and his death.
No. 19-1257 11
may have helped determine whether Reader would have died
regardless of the second dose.
The record demonstrates Anderson’s counsel did not con-
duct an investigation into the factual basis for the death re-
sults enhancement. “In the plea bargaining context, reasona-
bly competent counsel will attempt to learn all of the facts of
the case, make an estimate of a likely sentence, and communi-
cate the results of that analysis before allowing his client to
plead guilty.” Gaylord v. United States, 829 F.3d 500, 506 (7th
Cir. 2016) (citation and internal quotation marks omitted).
While it is unclear the extent to which Anderson’s counsel un-
derstood that the government was required to prove but-for
causation as an element of Anderson’s charged offense under
Burrage, at Anderson’s change-of-plea and sentencing hear-
ings she suggested that there could be a “causation issue” re-
garding whether the heroin that caused Reader’s death came
from Anderson. Nonetheless, Anderson’s counsel admitted in
her affidavit to the district court that she “never discussed
James Reader’s toxicology results with anyone trained in tox-
icology,” even though she herself was “not trained to inter-
pret toxicology results.” Although Anderson’s counsel stated
that she showed the toxicology results to Anderson, nothing
in the record suggests that he could interpret them either. Fi-
nally, while Anderson’s counsel may have discussed “the
possibility of hiring a medical examiner” with him, the record
is silent as to what, if any, advice she provided Anderson
about the cause of Reader’s death and the death results en-
hancement to enable Anderson to make an informed decision
whether to hire an expert, let alone plead guilty. Anderson
thus may have a viable claim of deficient performance. See
Miller v. United States, 940 F.3d 371, 375 (7th Cir. 2019)
12 No. 19-1257
(emphasizing that a defendant’s decision to plead guilty must
be adequately “informed by counsel’s advice”).
This case bears many factual similarities to Gaylord v.
United States, upon which both parties here rely. In that case,
Gaylord pleaded guilty to drug crimes under § 841(a)(1) and
received the death results enhancement because a user died
after ingesting oxycodone distributed by Gaylord, as well as
cocaine from another source. 829 F.3d at 503. The postmortem
and forensic pathology reports listed the cause of death as
“oxycodone and cocaine intoxication.” Id. Gaylord brought a
§ 2255 petition, arguing that his counsel provided ineffective
assistance by failing to adequately investigate his case and to
provide him with the medical reports so that he could make
an informed decision whether to plead guilty. Id. at 504. He
further argued that his counsel failed to challenge the appli-
cation of the death results enhancement to his sentence. Id. We
agreed that, if proven, these alleged errors would constitute
deficient performance. Id. at 508. We concluded that the evi-
dence did not show that Gaylord’s oxycodone “was the but-
for cause of death” because the medical reports indicated that
the cocaine concentration alone may have been enough to re-
sult in death. Id. at 507. Nor did the record show that the ox-
ycodone “was an independently sufficient cause of death.” Id.
at 508. Because the district court did not hold a hearing, the
record did not show whether his counsel was aware of the
but-for causation standard, examined the medical reports,
and provided Gaylord with the information necessary for a
knowing and voluntary guilty plea. Id. We therefore held that
he had sufficiently alleged ineffective assistance and re-
manded for a hearing. Id. at 508–09.
No. 19-1257 13
The chief factual issue in this case is essentially the same:
whether drugs distributed by the defendant were a but-for
cause of death. The most significant difference from Gaylord
is that Reader took two separate doses of the same drug, ob-
tained from different sources, rather than ingesting two dif-
ferent drugs (aside from Benadryl also found in his system).
Although Anderson’s counsel showed him the toxicology re-
sults, unlike defense counsel in Gaylord, that distinction is in-
applicable here because nothing in the record suggests An-
derson or his counsel could interpret those results. Accord-
ingly, as in Gaylord, Anderson has alleged facts sufficient to
support his claim that his counsel performed deficiently by
failing to investigate whether his heroin was the but-for cause
of death, and to communicate the results of that investigation
to Anderson to enable him to make an informed plea.
The government argues that Anderson has not sufficiently
alleged deficient performance by his counsel because he has
not made a “comprehensive” showing of what further inves-
tigation would have revealed. As we have noted previously,
“when the purported deficiency is based on a failure to inves-
tigate, we require the petitioner to allege what the investiga-
tion would have produced.” Long v. United States, 847 F.3d
916, 920 (7th Cir. 2017) (citation and internal quotation marks
omitted). Thus, the government contends that Anderson has
not shown what the results of an adequate investigation
would have been. The government also speculates that those
results actually may have hurt, rather than helped, Ander-
son’s case by confirming that the heroin he distributed was
the but-for cause of Reader’s death.
This speculative argument, however, discounts that An-
derson’s burden is only to “allege[] facts that, if proven,
14 No. 19-1257
would entitle him to relief.” Gaylord, 829 F.3d at 506 (citation
and internal quotation marks omitted). He is not required at
this stage to hire a toxicologist and prove the merits of further
investigation before the court.2 Anderson has alleged that
Reader ingested two doses of heroin before he died, only one
of which Anderson supplied, and that investigation into the
cause of Reader’s death may have undermined the govern-
ment’s evidence for the death results enhancement by show-
ing that the heroin unconnected to Anderson was inde-
pendently lethal. Construing this pro se filing liberally, these
allegations are sufficiently precise to satisfy Anderson’s bur-
den. See Wyatt v. United States, 574 F.3d 455, 459 (7th Cir. 2009)
(“Pro se collateral review filings are construed liberally.”).
The government also argues that the decision of Ander-
son’s counsel not to further investigate the cause of Reader’s
death was “a reasonable strategic choice” entitled to defer-
ence. Under Strickland, “strategic choices made after thorough
investigation of law and facts relevant to plausible options are
virtually unchallengeable.” 466 U.S. at 690; see also United
States v. Cieslowski, 410 F.3d 353, 360 (7th Cir. 2005) (“Gener-
ally when an attorney articulates a strategic reason for a deci-
sion, the court defers to that choice.”). According to her affi-
davit, Anderson’s counsel showed the postmortem and toxi-
cology reports to Anderson and discussed them with him. She
also stated that she considered engaging an expert to help in-
terpret the reports, but Anderson authorized her to proceed
2 In support of its argument, the government highlights Reader’s pur-
ported statement to a friend that he was not “high enough” after ingesting
the first dose. This statement by a person with no apparent medical train-
ing, and under the influence of drugs, is insufficient to prejudge the merits
of further investigation.
No. 19-1257 15
with plea negotiations without one. The government asserts
that these actions, combined with the likelihood that further
investigation would have reinforced that Anderson’s heroin
was the but-for cause of death, made the decision to secure a
plea agreement without further investigation reasonable.
We disagree. The Supreme Court has held that “counsel
has a duty to make reasonable investigations or to make a rea-
sonable decision that makes particular investigations unnec-
essary.” Strickland, 466 U.S. at 691. When an ineffective assis-
tance claim involves an allegedly inadequate investigation, “a
court must consider not only the quantum of evidence al-
ready known to counsel, but also whether the known evi-
dence would lead a reasonable attorney to investigate fur-
ther.” Wiggins v. Smith, 539 U.S. 510, 527 (2003). In other
words, “Strickland does not establish that a cursory investiga-
tion automatically justifies a tactical decision with respect
to … strategy. Rather, a reviewing court must consider the
reasonableness of the investigation said to support that strat-
egy.” Id.; see also Campbell v. Reardon, 780 F.3d 752, 766 (7th Cir.
2015) (“[T]he adequacy of the pretrial investigation … was
clearly established under Strickland as the critical threshold
question … .”).
Under the circumstances here, counsel’s decision not to
further investigate the available toxicology evidence was un-
reasonable. Whether heroin distributed by Anderson was a
but-for cause of Reader’s death was essential to the applica-
tion of the death results enhancement. Reader ingested mul-
tiple doses of heroin shortly before he died, only one of which
Anderson supplied. Further investigation of the toxicology
evidence could have therefore significantly informed
16 No. 19-1257
Anderson of the viability of a defense to that enhancement
and, consequently, whether to plead guilty.
Anderson’s counsel never attempted to discover what the
results of such an investigation might be, however, despite
her awareness that Reader had ingested heroin from multiple
sources. She could not interpret the toxicological evidence on
her own, nor did she consult with an expert who could. That
she showed the evidence to Anderson, a person with no rele-
vant medical or legal training, and that he authorized her to
proceed with plea negotiations without engaging an expert
does not make her performance constitutionally sufficient.
Given the obvious value of further investigation in this case,
we cannot view the decision of Anderson’s counsel to proceed
under these unique factual circumstances without investigat-
ing the causation issue as reasonable.
2. Prejudice
Having determined that Anderson has sufficiently alleged
that his counsel performed deficiently, we turn to the preju-
dice prong of the Strickland test. Anderson asserts that but for
his counsel’s deficient performance, he would have gone to
trial.3 “[A] mere allegation by the defendant that he would
have insisted on going to trial is insufficient to establish prej-
udice.” Cieslowski, 410 F.3d at 359 (quoting Berkey v. United
States, 318 F.3d 768, 772–73 (7th Cir. 2003)). Instead, “the
3 Anderson also argues that but for his counsel’s errors, he would have
bargained for a more favorable plea deal. Because we conclude that An-
derson can show prejudice based on the reasonable probability that he
would have gone to trial, we need not reach this argument. We do not
mean to hold, however, that Anderson is foreclosed from pursuing this
argument on remand.
No. 19-1257 17
defendant must show that there is a reasonable probability
that, but for counsel’s errors, he would not have pleaded
guilty and would have insisted on going to trial.” Hill v. Lock-
hart, 474 U.S. 52, 59 (1985). When a defendant alleges that his
counsel did not make an adequate investigation, whether
there is prejudice “will depend on the likelihood that discov-
ery of the evidence would have led counsel to change his rec-
ommendation as to the plea.” Id.
Anderson has alleged sufficient facts to support a claim of
prejudice. Without the death results sentencing enhancement,
Anderson’s Sentencing Guidelines range could have been as
low as 168 to 210 months’ imprisonment under U.S.S.G.
§ 2D1.1(c)(5), based on an offense level of 30 and a criminal
history category of VI. With the enhancement, Anderson
faced a mandatory life sentence under § 841(b)(1)(A) as an of-
fender with a prior drug felony conviction.
The government argues that other “unchallenged” factors
in the Presentence Investigation Report would have resulted
in a Guidelines range of 235 to 293 months, based on an of-
fense level of 33 and a criminal history category of VI. Ander-
son’s counsel originally objected to those factors, however,
and withdrew the objections after the court accepted Ander-
son’s plea under Federal Rule of Criminal Procedure
11(c)(1)(C). Had Anderson not entered into the plea agree-
ment, his counsel could have continued to challenge those
factors or sought to negotiate a more favorable sentence. See
Cieslowski, 410 F.3d at 364 (“A sentence imposed under a Rule
11(c)(1)(C) plea arises directly from the agreement itself, not
from the Guidelines … .”). Moreover, even if Anderson faced
a higher Guidelines range because of other factors, the
18 No. 19-1257
maximum sentence still would have been short of the manda-
tory life sentence he faced with the death results enhance-
ment.
The government also contends that even without the en-
hancement, because of his criminal history Anderson would
have faced a statutory minimum sentence of twenty years in
prison under § 841(b)(1)(A). Thus, a guilty verdict at trial
would have resulted in a sentence ranging from twenty years’
to life imprisonment. This argument, however, again misses
the mark. As the Supreme Court has instructed, “[w]hen a de-
fendant alleges his counsel’s deficient performance led him to
accept a guilty plea rather than go to trial, we do not ask
whether, had he gone to trial, the result of that trial ‘would
have been different’ than the result of the plea bargain.” Lee v.
United States, 137 S. Ct. 1958, 1965 (2017). Instead, we consider
“whether there was an adequate showing that the defendant,
properly advised, would have opted to go to trial.” See id. (cit-
ing Lockhart, 474 U.S. at 60). The decision whether to go to trial
or plead guilty involves “assessing the respective conse-
quences of a conviction after trial and by plea.” Id. at 1966.
“When those consequences are, from the defendant’s perspec-
tive, similarly dire, even the smallest chance of success at trial
may look attractive.” Id.; see also id. at 1966–67 (“For example,
a defendant with no realistic defense to a charge carrying a
20-year sentence may nevertheless choose trial, if the prose-
cution’s plea offer is 18 years.”).
Under the circumstances of this case, Anderson has ade-
quately alleged a reasonable probability that he would have
rejected the plea deal in favor of going to trial but for his at-
torney’s deficiencies. Had he received effective assistance,
Anderson would have had better insight into his likely
No. 19-1257 19
sentence if convicted at trial. If the government could prove
the basis for the death results enhancement, Anderson would
have faced a life sentence. Anderson’s § 2255 petition, how-
ever, questions the government’s ability to prove that basis.
Without the enhancement, Anderson would have faced a sen-
tence ranging from a statutory mandatory minimum of
twenty years—the same sentence he agreed to in his plea—to
a maximum of just over twenty-four years (under the higher
Guidelines range advocated by the government). Confronted
with such similar sentencing consequences, and with the pro-
spect of a life sentence off the table, Anderson may well have
decided that he had little to lose and much to gain by playing
the odds at trial rather than pleading guilty. While his pro-
spects of an acquittal may have been slim, “the possibility of
even a highly improbable result may be pertinent to the extent
it would have affected his decisionmaking.” Id. at 1967. Ac-
cordingly, we cannot conclude that it would be irrational for
Anderson to reject a twenty-year plea offer in favor of forcing
the government to prove its case at trial.
The “contemporaneous evidence” in the record substanti-
ates Anderson’s assertions about whether he would have
pleaded guilty “but for his attorney’s deficiencies.” Id. (ex-
plaining that courts “should not upset a plea solely because
of post hoc assertions from a defendant”). At the change-of-
plea hearing, Anderson asserted that “the James Reader situ-
ation is a lot more detailed than it says here.” He also stated
his understanding that Reader “bought some heroin from
someone outside of my conspiracy” and “took some pre-
scribed meds” in addition to the heroin distributed by Ander-
son. Although Anderson confirmed that he would not “dis-
pute” or “challenge” the government’s offer of proof, it is
20 No. 19-1257
apparent that he agreed to those facts because he did not want
the plea agreement to “change.” If his counsel had conducted
an adequate investigation of the government’s evidence for
the death results enhancement, there is a reasonable probabil-
ity that the outcome of the plea process would have been dif-
ferent.
Evidentiary Hearing
Anderson is entitled to an evidentiary hearing on his inef-
fective assistance of counsel claim if he has alleged “facts that,
if proven, would entitle him to relief.” Martin, 789 F.3d at 706
(citation and internal quotation marks omitted). Ineffective
assistance claims often require an evidentiary hearing to de-
velop the record more fully. See Osagiede v. United States,
543 F.3d 399, 413 (7th Cir. 2008). A district court need not
grant a hearing, however, if “the motion and the files and rec-
ords of the case conclusively show that the prisoner is entitled
to no relief.” 28 U.S.C. § 2255(b). Nor is a hearing required “if
the petitioner makes allegations that are ‘vague, conclusory,
or palpably incredible,’ rather than ‘detailed and specific.’”
Spiller v. United States, 855 F.3d 751, 754 (7th Cir. 2017) (quot-
ing Martin, 789 F.3d at 706).
Here, Anderson has alleged sufficient facts to warrant an
evidentiary hearing on his ineffective assistance of counsel
claim. At that hearing, Anderson’s counsel will have an op-
portunity to respond to Anderson’s allegations and to explain
whether she was aware of the but-for causation standard and
the extent to which she understood and consulted with An-
derson about the death results enhancement and the need to
hire an expert to interpret the toxicological evidence. See Gay-
lord, 829 F.3d at 506 (explaining that before allowing a client
to plead guilty, reasonably competent counsel will attempt to
No. 19-1257 21
learn the relevant facts of the case, estimate a likely sentence,
and communicate her analysis to the client); Osagiede,
543 F.3d at 409 (“All lawyers that represent criminal defend-
ants are expected to know the laws applicable to their client’s
defense.” (citation omitted)). Anderson’s counsel may have
consulted at length with Anderson about, or had strategic rea-
sons for, proceeding with plea negotiations without engaging
an expert, but the record before us contains insufficient infor-
mation to allow us to make this determination. Thus, we con-
clude that an evidentiary hearing is warranted.
III. Conclusion
For the foregoing reasons, we VACATE the decision of the
district court and REMAND to the district court for an eviden-
tiary hearing on Anderson’s § 2255 petition.