Monta Anderson v. United States

In the

United States Court of Appeals
For the Seventh Circuit
____________________
No. 22-2666
MONTA ANDERSON,
Petitioner-Appellant,
v.

UNITED STATES OF AMERICA,
Respondent-Appellee.
____________________

Appeal from the United States District Court for the
Central District of Illinois.
No. 17-cv-01542 — Michael M. Mihm, Judge.
____________________

ARGUED MAY 19, 2023 — DECIDED FEBRUARY 26, 2024
____________________

Before FLAUM, ROVNER, and ST. EVE, Circuit Judges.
ROVNER, Circuit Judge. In this collateral challenge to his
conviction, see 18 U.S.C. § 2255, petitioner Monta Anderson
seeks to vacate his guilty plea on the ground that it was not
knowing and voluntary due to his plea counsel’s alleged in-
effective assistance. Specifically, Anderson asserts that his
counsel advised him to plead guilty to conspiring to distrib-
ute heroin in violation of 21 U.S.C. § 841(a)(1) (effective Aug.
2 No. 22-2666

3, 2010 to Dec. 20, 2018), 1 stipulate to having distributed her-
oin that resulted, inter alia, in the death of James Reader, see
§ 841(b)(1)(A), and accept an agreed-upon sentence of 20
years pursuant to Federal Rule of Criminal Procedure
11(c)(1)(C)—ostensibly in order to avoid a potential manda-
tory minimum prison term of life—without first consulting
with a toxicology expert on the question of whether the heroin
Anderson distributed was in fact a but-for cause of Reader’s
death. See Burrage v. United States, 571 U.S. 204, 218–19, 134
S. Ct. 881, 892 (2014). When this case was last before us, we
concluded that Anderson had articulated a viable claim of at-
torney ineffectiveness and remanded for an evidentiary hear-
ing. See Anderson v. United States, 981 F.3d 565, 577–78 (7th Cir.
2020) (“Anderson I”).
Based on the testimony presented at that hearing, Ander-
son has now shown that consultation with a toxicology expert
would have revealed the government’s inability to prove be-
yond a reasonable doubt that the heroin he supplied to
Reader was a but-for cause of Reader’s death. Within the
framework of our prior opinion, that showing likely would
have been sufficient to establish that his plea counsel indeed
was ineffective for failing to consult with such an expert. As
the case was briefed and argued to us previously, it was the
death-results enhancement that drove the prospective man-
datory minimum prison term of life. The government did not
dispute that if consultation with a medical expert would have
revealed that the prosecution could not meet its burden of
proof as to that enhancement, a mandatory sentence of life in

1 Unless otherwise indicated, our citations to section 841 are to the

2010 version in effect at the time of the offense and when Anderson was
indicted in 2013.
No. 22-2666 3

prison would have been off the table and Anderson would
have faced, at worst, a mandatory minimum term of 20 years,
not life. Consistent with the premise of our prior opinion, An-
derson would have thus established that he was prejudiced
by his plea counsel’s ineffectiveness.
However, the government now argues that there were two
other grounds on which Anderson would have been subject
to a mandatory life term apart from the death-results en-
hancement, such that Anderson was not prejudiced by his
counsel’s failure to consult with a toxicologist. This line of ar-
gument was developed on remand and relied upon by the
district court below in denying Anderson relief. Although it
turns out that Anderson’s criminal history did not meet the
criteria for one of these two alternative bases for a mandatory
life term, we do agree that Anderson would have faced a man-
datory life term given that he had at least one prior felony
drug conviction and two individuals suffered serious bodily
injuries when they overdosed on heroin that Anderson had
supplied and required urgent intervention to resuscitate
them. See § 841(b)(1)(A).
For this reason, we agree with the district court that An-
derson ultimately was not prejudiced by any ineffectiveness
on the part of his plea counsel: given that a mandatory life
term remained on the table even without the death-results en-
hancement, pleading guilty and securing the benefit of a 20-
year term was an eminently reasonable, positive outcome for
Anderson. We therefore affirm the district court’s judgment.
I.
Beginning in 2010, Anderson participated in a conspiracy
to distribute heroin in central Illinois. Anderson obtained the
4 No. 22-2666

heroin from a supplier in Chicago and distributed it to both
dealers and users in central Illinois. Among the dealers whom
Anderson supplied was Anthony Mansini. The pre-sentence
report (“PSR”) adopted by the district court at sentencing es-
timated conservatively that Anderson’s overt acts in further-
ance of the conspiracy involved 1.6 kilograms of heroin; of
that total, Anderson distributed 900 grams to Mansini. Crim.
R. 111 at 6, 8 (Revised PSR ¶¶ 25, 35). 2
On August 25, 2012, during the course of the conspiracy,
Reader made two purchases of heroin. The first was from a
dealer in Peoria unconnected to either Mansini or Anderson.
Reader ingested that heroin early in the afternoon but indi-
cated to the person with whom he was using heroin that he
was not experiencing the high he desired. He then purchased
heroin for a second time, this time from Mansini, who in turn
had obtained the heroin from Anderson. After Reader in-
gested that second quantity of heroin, he died. The toxicology
report on Reader would indicate the presence of both heroin
metabolites (including morphine) and Benadryl in his system.
The coroner’s report identified the cause of Reader’s death as
“opiate intoxication” (R. 66-2 at 70) but did not attribute the
death to either the first or second doses of heroin that Reader
consumed, nor did it make findings as to the incremental ef-
fects of any other drugs in Reader’s system. In junior and sen-
ior high school, Reader had been a star athlete with a strong
academic record who dreamed of playing college basketball
and studying marine biology, but those dreams were derailed

2 References to “Crim. R.” are to the record in the criminal case that

culminated in Anderson’s guilty plea and conviction, No. 1:13–cr–10064–
MMM-JEH. References to “R.” are to the record in the civil case that re-
solved Anderson’s section 2255 motion.
No. 22-2666 5

when he began using heroin at age 18. He had struggled with
addiction and had overdosed on five prior occasions, but ac-
cording to his parents, he was in recovery, was working a
steady job, and had refrained from heroin use in the eleven
months prior to his fatal relapse. Reader was 21 years old.
Also during the course of the conspiracy, between Sep-
tember and early November 2012, two other individuals over-
dosed on heroin that Anderson purportedly had supplied:
Haley Heilman and William Holmes. Heilman was a criminal
associate of Anderson’s: beginning in 2011, she regularly
drove him to Chicago to pick up heroin from his supplier, and
he compensated her with user-quantities of heroin. Crim.
R. 111 at 5 (Revised PSR ¶ 17). Heilman overdosed twice: on
the first occasion in October 2012, after ingesting heroin she
had obtained from Mansini—which Mansini had obtained
from Anderson—Heilman was revived by paramedics with
Narcan® 3 en route to a hospital; on the second occasion, in late
October or early November 2012, after ingesting heroin she
and a co-defendant had purchased directly from Anderson,
Heilman was once again revived at the hospital with Narcan®.
Crim. R. 111 at 6 (Revised PSR ¶¶ 28–29). Holmes was one of
Mansini’s customers: he initially purchased user-sized quan-
tities of heroin from Mansini and over time began to make
larger, distribution-sized purchases. Holmes overdosed in
September or October 2012 after buying heroin from Jesse
Peak, who in turn had obtained the heroin from Mansini.
Mansini’s primary source of heroin at that time was Ander-
son. Holmes was revived with cardio-pulmonary resuscita-
tion (“CPR”) administered by a friend who noticed that he

3 Narcan® is a brand name for naloxone, a medication that works as

an opioid antagonist to reverse the effects of an opioid overdose.
6 No. 22-2666

had stopped breathing and his face had turned blue. R. 111 at
7 (Revised PSR ¶ 30).
A grand jury indicted Anderson and four co-defendants
in May 2013 with conspiring to distribute heroin in violation
of 21 U.S.C. §§ 841(a)(1) and 841(b)(1)(A). (The charged con-
spiracy involved more than those five individuals; others
were charged separately.) The indictment alleged that the
conspiracy began in 2010 and continued through the date of
the indictment, that it involved over 1000 grams of heroin,
and had resulted in death and serious bodily injury. The gov-
ernment also filed two notices pursuant to 21 U.S.C. § 851
identifying three prior felony drug convictions that would
trigger statutory enhancements to Anderson’s prospective
sentence: a 2006 conviction in Lake County, Illinois for pos-
session of cocaine; a 2009 conviction in Lake County for at-
tempted possession of heroin; and a 2013 conviction in Peoria
County, Illinois for unlawful possession of heroin. Addition-
ally, there were two other felony drug convictions in Ander-
son’s criminal history not included in the section 851 notices
that potentially might qualify as predicates sufficient to trig-
ger an enhanced statutory penalty: a 2000 conviction in Cook
County, Illinois for possession of 30–500 grams of cannabis
and another conviction from the same year, also in Cook
County, for the manufacture/delivery of 1–15 grams of co-
caine.
Given Anderson’s criminal history and the events that
took place over the course of the conspiracy, there were three
ways that Anderson potentially could be subject to a manda-
tory life term: (1) at least two of Anderson’s prior convictions
qualified as felony drug offenses, as defined in 21 U.S.C.
§ 802(44); (2) one of his prior convictions qualified as a felony
No. 22-2666 7

drug offense and death resulted from the heroin that Ander-
son distributed, or (3) one of his prior convictions qualified as
a felony drug offense and serious bodily injury resulted from
the heroin that Anderson distributed. § 841(b)(1)(A)(i).
Also, as the government pointed out at the evidentiary
hearing below and in its brief on appeal, there were three
ways that Anderson could be subject to a mandatory mini-
mum term of 20 years in prison (with a maximum possible
term of life): (1) at least one of Anderson’s prior convictions
constituted a felony drug offense, 4 (2) death resulted from the
heroin that Anderson distributed, or (3) serious bodily injury
resulted from the heroin that Anderson distributed.
§ 841(b)(1)(A)(i).
After private counsel withdrew from representing Ander-
son in August 2014, the district court appointed attorney
Michelle N. Schneiderheinze to represent Anderson pursuant
to the Criminal Justice Act. Schneiderheinze represented An-
derson for the remainder of the criminal proceedings in the
district court. It was Schneiderheinze who negotiated the Rule
11(c)(1)(C) plea agreement at issue here.
Schneiderheinze would later testify that she believed there
were factual grounds on which to challenge the government’s
theory that Anderson had supplied the second dose of heroin
to Reader (for example, Mansini had made conflicting state-
ments about the source of the heroin he sold to Reader) and
that the second dose was a but-for cause of Reader’s death,
but that it would have been necessary for her to consult with

4 Section 401(a)(2)(A) of the First Step Act of 2018, P.L. 115-391, 132

Stat. 5194, 5220 (Dec. 21, 2018), reduced the penalty for this aggravating
factor from 20 to 15 years.
8 No. 22-2666

a toxicologist in order to fully evaluate the strength of the gov-
ernment’s case on the latter point. However, in the course of
negotiating the plea, the prosecutor was adamant that Ander-
son stipulate to being responsible for Reader’s death. And as
we discuss below, Schneiderheinze believed that there was a
real possibility that Anderson might receive a mandatory sen-
tence of life if he proceeded to trial even if he ultimately pre-
vailed on the death-results issue, so she thought the 20-year
deal was a good one and advised Anderson to take it. “It was
the best sentencing outcome for him that I thought I could
get,” Schneiderheinze testified. R. 52 at 192–93. “And it was
guaranteed.” R. 52 at 193.
Pursuant to the plea agreement dated February 3, 2015,
Anderson agreed to plead guilty and accept a sentence of 20
years’ imprisonment. He stipulated in the agreement that “the
government will prove that as an overt act of this conspiracy
[Anderson] provided the heroin that led to the death of James
Reader and the serious bodily injury suffered … as a result of
heroin overdose of Haley Heilman and William Holmes.”
Crim. R. 81 at 12 (Plea Agreement ¶ 22). In his plea colloquy,
Anderson acknowledged having at least one prior felony
drug conviction and that without the agreement he faced a
minimum prison term of 20 years up to a maximum term of
life. As for the “death-results” enhancement, he indicated that
the facts regarding Reader’s death were not as straightfor-
ward as the plea agreement made them out to be, but for pur-
poses of his plea he would not dispute that his heroin distri-
bution caused Reader’s death. R. 125 at 19, 36–41. Pursuant to
the plea agreement, Anderson waived the right to challenge
his conviction and sentence except as to the ineffectiveness of
his counsel. R. 81 at 5–6 (Plea Agreement ¶ 12). The district
No. 22-2666 9

judge postponed his decision on whether to accept the guilty
plea pending review of the PSR.
The probation officer’s PSR indicated that, absent the plea
agreement’s specified sentence of 20 years, the Sentencing
Guidelines would call for a sentence of life. The probation of-
ficer found Anderson responsible for distributing a total of 1.6
kilograms of heroin, and because Reader’s death resulted
from Anderson’s heroin distribution, the base offense level
was 43. Crim. R. 111 at 10 (Revised PSR ¶ 43); see U.S.S.G. §
2D1.1(a)(1) (Nov. 2014). Anderson’s possession of a gun dur-
ing the charged conspiracy added two levels, § 2D1.1(b)(2),
and his role as a manager or supervisor added another three
levels, § 3B1.1(b), whereas his acceptance of responsibility in
pleading guilty brought the adjusted offense level down two
levels, § 3E1.1(a) to a nominal level of 46. Crim. R. 111 at 10–
11 (Revised PSR ¶¶ 44, 46, 50). But because the Guidelines
identify level 43 as the maximum offense level for all but the
most extreme cases, 43 was the final adjusted offense level.
U.S.S.G. Ch. 5, Pt. A comment. (n.2); Crim. R. 111 at 11 (Re-
vised PSR ¶ 52). Coupled with Anderson’s criminal history
category of VI, the Guidelines called for a sentence of life in
prison. Crim. R. 111 at 26 (Revised PSR ¶ 132). But subject to
the district judge’s acceptance of the Rule 11(c)(1)(C) agree-
ment, the agreed-upon sentence of 20 years would bind the
court and supplant the advisory Guidelines sentence. R. 111
at 26 (Revised PSR ¶134).
At the sentencing hearing in October 2015, the district
judge formally accepted the plea agreement after questioning
the parties’ counsel at some length about the facts of the case
and the rationale underlying the agreed-upon sentence of 20
years. The judge indicated he came “very close” to rejecting
10 No. 22-2666

the agreement given the seriousness of the offense—in addi-
tion to Reader’s death, which was attributed to Anderson, an
additional three or four deaths were attributed to Mansini—
and the life term specified by the statute and the Guidelines.
R. 126 at 37. But the judge was ultimately satisfied that there
were material differences between Anderson and Mansini
(who had been sentenced to a 24-year term) and that the plea
agreement “[was] minimally sufficient given all the various
sentencing factors.” R. 126 at 37. The judge sentenced Ander-
son to the agreed-upon term of 240 months, with credit for the
17 months Anderson had served on a state conviction (the
2013 Peoria County conviction) that involved relevant con-
duct vis-á-vis the federal conspiracy, for a total of 223 months.
Not long after he was sentenced, Anderson began to re-
think his plea and filed his first appeal, which this court later
dismissed pursuant to Anders v. California, 386 U.S. 738, 87
S. Ct. 1396 (1967), as lacking any non-frivolous issue to pur-
sue. United States v. Anderson, 650 F. App’x 274 (7th Cir. 2016).
While that appeal was pending, Anderson filed a motion to
withdraw his guilty plea, which the district court denied; this
court subsequently held in a second appeal that the district
court lacked jurisdiction over that motion given that his direct
appeal was pending at the time. United States v. Anderson, 670
F. App’x 407 (7th Cir. 2016).
Finally, Anderson filed a pro se section 2255 motion which
contended that his guilty plea was not knowing and volun-
tary because he received ineffective assistance of counsel in
connection with the plea decision and that but for his attor-
ney’s errors, he would not have accepted the plea agreement
and would not have pleaded guilty. Anderson’s motion was
focused on the death-results enhancement. He argued that
No. 22-2666 11

Schneiderheinze did not adequately discuss with him the
government’s burden under Burrage to prove beyond a rea-
sonable doubt that the heroin he distributed was a but-for
cause of Reader’s death. 571 U.S. at 210, 218–19, 134 S. Ct. at
887, 892. Nor, Anderson alleged, did Schneiderheinze ade-
quately investigate the cause of Reader’s death. Had she done
so, he contended, she would have realized that the govern-
ment could not meet its burden under Burrage. R. 10.
At the government’s request, the district court ordered
Schneiderheinze to submit an affidavit in response to Ander-
son’s section 2255 motion. Among other points, the court di-
rected Schneiderheinze to discuss what advice she had given
Anderson regarding the death-results enhancement. R. 13.
On that point, the narrow affidavit that Schneiderheinze pre-
pared indicated that: (1) She had shared with Anderson the
discovery materials the government had produced, including
the toxicologist’s report regarding Reader; (2) Anderson was
aware of the need for a medical expert to interpret the medical
reports concerning Reader’s death; (3) Anderson authorized
Schneiderheinze to engage in plea negotiations without hir-
ing a medical expert; and (4) Schneiderheinze was not trained
to interpret the Reader toxicology results and had not dis-
cussed those results with anyone who had such training, so
she could not assess the validity of Anderson’s doubts regard-
ing the cause of Reader’s death. R. 16-1.
For its part, the government urged the district court to
deny Anderson’s section 2255 motion. In its view, Schneider-
heinze had been effective in negotiating a plea agreement that
avoided a mandatory sentence of life. The government also
argued that there was no evidentiary support for the notion
that consulting with a medical expert would have enabled
12 No. 22-2666

Anderson to defeat the death-results enhancement. In its
memorandum, the government made no mention of any
other basis on which Anderson faced a life sentence apart
from the death-results enhancement coupled with one prior
felony conviction for a drug offense. R. 16. 5
The district court denied the section 2255 motion without
an evidentiary hearing. R. 18. Having presided over Ander-
son’s change-of-plea hearing, the judge was satisfied that An-
derson had knowingly and voluntarily pleaded guilty, and
specifically that he did so despite his awareness that he might
have a factual defense to the death-results enhancement. R. 18
at 5–6. “[Anderson’s] current 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 court.” R. 18
at 6. And because the record before the court indicated that
Schneiderheinze had provided Anderson with the effective
assistance of counsel during the plea negotiations, R. 18 at 5,
the district court concluded that there was no need for further
inquiry into the validity of Anderson’s plea.
Anderson appealed. Although the district court had de-
nied Anderson a certificate of appealability, see 28 U.S.C.
§ 2253(c), this court granted him such a certificate and ap-
pointed counsel to represent him on appeal.
As Anderson framed his ineffectiveness claim in that ap-
peal, it was the death-results enhancement that drove the pro-
spective sentence of life and in the absence of that

5 The government did point out that the plea agreement incorporated

the parties’ stipulation that Anderson was subject to a 20-year minimum
term and a maximum term of life because Anderson’s heroin distribution
resulted in death and serious bodily injury. R. 16 at 2.
No. 22-2666 13

enhancement, a mandatory life term would have been off the
table. 6 At worst, Anderson postulated, he would have been
subject to a statutory minimum term of 20 years, and perhaps
an advisory Guidelines sentence of slightly more than that.
For that reason, it was ineffective for his plea counsel not to
look further into the cause of Reader’s death. Had Schneider-
heinze consulted with a medical expert, Anderson reasoned,
she would have discovered that the government would not
be able to prove beyond a reasonable doubt that Anderson’s
heroin was a but-for cause of Reader’s death.
On the premise that, absent the death-results enhance-
ment, he was facing at most a mandatory minimum prison
term of 20 years, Anderson argued that Schneiderheinze’s
failure to investigate and demonstrate the lack of evidentiary
support for the enhancement prejudiced him in that he would
have opted for trial rather than pleading guilty, knowing that
even if convicted he was likely to face a sentence at or near
the 20-year term for which the plea agreement provided. See
Lee v. United States, 582 U.S. 357, 364–65, 371, 137 S. Ct. 1958,
1965, 1968–69 (2017); Hill v. Lockhart, 474 U.S. 52, 59, 106 S. Ct.
366, 370 (1985); see also Brock-Miller v. United States, 887 F.3d
298, 311–12 (7th Cir. 2018) (discussing variations on the Hill
standard for cases in which counsel’s ineffectiveness has led

6 Anderson’s briefs in the prior appeal tended to focus on what the

advisory Guidelines sentence might be depending on whether he was
deemed responsible for Reader’s death, but of course it is the statute itself
which imposes mandatory minimum terms depending on particular ag-
gravating factors. See § 841(b)(1)(A)(i).
14 No. 22-2666

defendant to opt for trial rather than plead guilty or has
caused him not to accept earlier, more favorable plea offer). 7

7 Secondarily, Anderson also postulated that Schneiderheinze, armed

with a strong defense to the death-results enhancement, might have been
able to negotiate a more favorable plea agreement, i.e., one calling for a
term of less than 20 years. We note that this circuit has yet to accept as
valid a prejudice theory positing that absent plea counsel’s ineffectiveness,
the defendant would have negotiated a different, more favorable plea
agreement. See Bethel v. United States, 458 F.3d 711, 720 & n.14 (7th Cir.
2006); see also United States v. Dominguez, 998 F.3d 1094, 1116–17 (10th Cir.
2021) (expressing doubt as to the validity of this theory of prejudice and
collecting cases, including Bethel). Our more recent opinion in Brock-Miller
notes that the Supreme Court’s decision in Missouri v. Frye, 566 U.S. 134,
148, 132 S. Ct. 1399, 1409–10 (2012), comes the closest to establishing a prej-
udice standard for situations in which, but for counsel’s ineffectiveness, a
better plea agreement might have been negotiated without the specter of
an improper sentence enhancement—in Brock-Miller, a recidivist enhance-
ment—hanging over the negotiations. 887 F.3d at 312. Frye concerned plea
offers that defense counsel never communicated to the defendant and
which then expired; the terms of those offers were significantly more fa-
vorable than the sentence the defendant ultimately received pursuant to a
blind guilty plea. The petitioner in Brock-Miller alleged that had her coun-
sel recognized that she was not subject to the recidivist enhancement, she
would have rejected the government’s plea offer and either gone to trial
or negotiated a better plea agreement consistent with the deals entered
into by multiple co-defendants who had pleaded guilty to reduced drug
quantities or lesser included offenses. We remanded for an evidentiary
hearing as to both of these alternative theories of prejudice. Id. at 313. On
remand, the parties resolved the case by agreement without a hearing and
findings by the court. Thus, although Brock-Miller may have left the door
open to a finding of prejudice based on the prospect of negotiating a better
plea deal than the one the defendant entered into, we have yet to fully
embrace and define the boundaries of such a theory. Consistent with our
previous opinion, we refrain from exploring the merits of this theory here
and instead confine ourselves to Anderson’s first and primary theory of
(continued)
No. 22-2666 15

Notably, the government’s response brief implicitly ac-
cepted the premise of Anderson’s appellate case. Nowhere in
its brief did the government argue that, wholly apart from the
death-results enhancement, Anderson potentially faced a
statutory minimum term of life in prison, whether due to the
serious bodily injury enhancement in combination with one
prior felony drug conviction, or due to two prior felony drug
convictions. 8 Instead, the government argued that because,
without the death-results enhancement, Anderson still faced
a 20-year statutory minimum term and a Guidelines sentenc-
ing range topping out at a bit more than 24 years—in other
words, a sentence either the same as, or somewhat worse than
the one specified in his plea agreement—he could not show
that he was prejudiced by any ineffectiveness on his attor-
ney’s part in failing to consult with a medical expert regard-
ing the death-results enhancement.
With the case presented to us on those terms, we vacated
the district court’s judgment and remanded with directions to
conduct an evidentiary hearing. Anderson, 981 F.3d 565. We

prejudice, which is that he would have taken his chances at trial had he
realized that the government would not be able to sustain its burden of
proof as to the death-results enhancement.
8 The government’s brief, while outlining section 841 and its penalty

structure, did note briefly that the enhancement for a serious bodily injury,
coupled with one prior felony drug conviction, could trigger a statutory
mandatory minimum term of life; its counsel acknowledged the same at
oral argument in response to a question from a panel member. Appeal No.
19-1257, R. 24 at 15, 41 (Gov. Br. at 8, 34 & n.8); Oral Arg. 10-29-2020 at
23:40–24:44. Even so, the government did not cite the serious-bodily-in-
jury enhancement or another path to a life term as a reason why any inef-
fectiveness on the part of Schneiderheinze in failing to investigate the
death-results enhancement did not prejudice Anderson.
16 No. 22-2666

confined our analysis to Anderson’s first and principal theory
of prejudice: that had his counsel provided effective assis-
tance as to the death-results enhancement, he would not have
accepted the terms of the plea agreement and would not have
pleaded guilty. The record indicated that Schneiderheinze
had not conducted an investigation into the death-results en-
hancement: specifically, she had not consulted with a toxicol-
ogist or other medical expert. We accepted the premise of An-
derson’s contention that, had counsel looked more closely at
the factual basis for the death-results enhancement, she
would have realized there was a meritorious defense to the
enhancement: given that Reader had ingested two heroin
doses on the day he died, only the second of which came from
Anderson, it was possible that the first dose, whether alone or
in combination with the Benadryl found in his system, might
have been independently sufficient to cause his death. Id. at
573–76.
Anderson also asserted that but for his counsel’s deficient
performance, he would have gone to trial rather than accept-
ing the plea agreement, and we agreed with him that he had
made a sufficient preliminary showing of prejudice in this re-
gard to warrant a hearing. Specifically, Anderson alleged that
absent the death-results enhancement, he was facing a Sen-
tencing Guidelines range that might have been as low as 168
to 210 months’ imprisonment, whereas with the enhance-
ment, he was looking at a mandatory life term. Although the
government argued that the Guidelines range actually would
have been 235 to 293 months, based on multiple sentencing
factors that it understood to be undisputed, Anderson
pointed out that his plea counsel had originally raised objec-
tions with respect to those factors and had withdrawn them
solely on the basis of the plea agreement. “Moreover, even if
No. 22-2666 17

Anderson faced a higher Guidelines range because of other
factors, the maximum sentence still would have been short of
the mandatory life sentence he faced with the death-results
enhancement.” Id. at 577.
We confronted and rejected the government’s contention
that even without the death-results enhancement, in view of
Anderson’s criminal history, he would have faced a statutory
minimum sentence of 20 years under section 841(b)(1)(A),
such that a guilty verdict at trial would have resulted in a sen-
tence of at least 20 years and possibly up to life. We said that
argument “misses the mark.” Id. We explained that the rele-
vant question as to this type of ineffectiveness claim is not
whether Anderson would have done better at trial, but rather
whether, had he been properly advised by counsel, he would
have opted to go to trial rather than taking the plea. Id.
Under the circumstances of this case, Anderson
has adequately alleged a reasonable probability
that he would have rejected the plea deal in fa-
vor of going to trial but for his attorney’s defi-
ciencies. Had he received effective assistance,
Anderson would have had better insight into
his likely 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 pe-
tition, however, questions the government’s
ability to prove that basis. Without the enhance-
ment, Anderson would have faced a sentence
ranging from a statutory mandatory minimum
of twenty years—the same sentence he agreed
to in his plea—to a maximum of just over
18 No. 22-2666

twenty-four years (under the higher Guidelines
range advocated by the government). Con-
fronted with such similar sentencing conse-
quences, and with the prospect 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 prospects 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.” 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.
Id. at 577–78 (citation omitted).
Note two important points about the panel’s prior opin-
ion. First, the court assumed that without the death-results
enhancement, Anderson would not have faced a mandatory
life term. Presumably this was because the government did
not make clear that there were other routes to a mandatory
life term in this case even absent the death-results enhance-
ment. Second, although the government did make clear that
even without the death-results enhancement, there were
grounds for subjecting Anderson to a 20-year mandatory
minimum, which was the same sentence he received on his
guilty plea, the court unequivocally rejected the notion that
this defeated a finding that Anderson was prejudiced by his
attorney’s purported ineffectiveness. Rather, the court rea-
soned that even if Anderson would face the same or a some-
what longer sentence if he were convicted at trial, Anderson
No. 22-2666 19

could still show that he would have taken his chances and
proceeded to trial rather than accepting the plea deal.
The case then proceeded to an evidentiary hearing on re-
mand. Schneiderheinze testified that, under the circum-
stances, she thought the 20-year term called for by the plea
agreement was the best possible deal her client could obtain.
She represented that her client was aware of Burrage and the
need to consult with an expert in order to assess whether the
government would be able to prove, in compliance with Bur-
rage, that the heroin distributed by Anderson was a but-for
cause of Reader’s death. Schneiderheinze believed that the
defense otherwise had a good case on the death-results is-
sue—indeed, she assumed that her client might have pre-
vailed on a challenge to this enhancement had she and An-
derson decided to pursue it—but the government would not
drop it and would not agree to a term of 20 years unless An-
derson acknowledged that his heroin distribution had re-
sulted in Reader’s death. She also understood that the govern-
ment had other ways of triggering a mandatory minimum
term of life, whether by showing that Anderson was respon-
sible for inflicting serious bodily injuries on Heilman or
Holmes and had one prior felony drug conviction, or by
showing that Anderson had two prior felony drug convic-
tions. In view of those alternatives, Schneiderheinze did not
believe it was necessary to consult with an expert before ad-
vising her client to accept the plea deal and stipulate to re-
sponsibility for Reader’s death, as Anderson would still be
facing a prison term far worse than the agreed-upon 20-term
without the death-results enhancement. She explained that
she had not discussed these alternative pathways to a life
term in the affidavit she filed previously at the district court’s
instruction, given that Anderson’s ineffectiveness claim was
20 No. 22-2666

focused on the death-results enhancement and she did not be-
lieve her former client’s waiver of attorney-client privilege ex-
tended beyond that enhancement, so she had limited her affi-
davit accordingly.
Dr. Steven Aks, an emergency-care physician and medical
toxicologist, testified for Anderson that apart from the drugs
tested for and detected in Reader’s system, the evidence re-
vealed that Reader had prescriptions for two other drugs that,
if Reader ingested them on the day of his overdose, might
have contributed to his death. Reader had a prescription for
Clonazepam, a sedative medication which can depress
breathing, but the coroner had not tested for that drug.9 A po-
lice report indicated that Reader had taken three yellow
pills—which could have been Clonazepam—on the day of his
death, before he took the first dose of heroin; apart from that,
it was unknown whether Reader took Clonazepam or any
other medication later in the day. There were no pills found
in Reader’s digestive system, but he had vomited prior to his
death and there was no evidence in the record as to the con-
tents of the vomitus. Reader also had a prescription for Sub-
oxone® to treat opioid abuse. Suboxone®, by preventing some-
one from experiencing a high, could cause the individual to
inject more heroin. Again, the coroner had not tested for the
presence of that drug in Reader’s system. Dr. Aks could not
rule out the possibility of heroin overdose as a cause of death,
but his opinion was that Reader’s death was the result of a

9 The police report regarding Reader’s death indicates that he had a

prescription filled for 120 Clonazepam pills on August 23, 2012, two days
before he died, but there were only 67 pills left in the bottle found at the
scene of his death.
No. 22-2666 21

polydrug overdose, and the evidence was inconclusive as to
which drug led to his death.
The government did not put on its own evidence on the
death-results question. At least for purposes of this appeal, it
appears to have implicitly conceded that in view of Dr. Aks’
testimony, the prosecution likely would not prevail on the
death-results issue if the case proceeded to trial. 10 Instead, the
government’s focus on remand was on the question of preju-
dice and specifically whether, absent the death-results en-
hancement, Anderson would have faced a statutorily-man-
dated term of life in prison in view of the serious bodily inju-
ries suffered by Heilman and Holmes and his multiple prior
felony drug convictions.
Regarding Anderson’s criminal history, a question arose
near the end of the hearing below whether Anderson’s 2006
and 2009 Illinois convictions actually qualified as predicate
felony drug offenses under section 802(44), 11 and the district
court ordered briefing on that point. Recall that these were
two of the three convictions the government cited in its

10 We note that the district judge found Dr. Aks to be a “very good”

witness who was “very balanced with his testimony.” R. 52 at 241. The
judge also noted, however, that apart from the missing Clonazepam pills,
there was no evidence to affirmatively support the notion that Reader had
taken any additional medications prior to his death.
11 Section 802(44) provides: “The term ‘felony drug offense’ means an

offense that is punishable for more than one year under any law of the
United States or of a State or foreign country that prohibits or restricts
conduct relating to narcotic drugs, marihuana, anabolic steroids, or de-
pressant or stimulant substances.” Elsewhere, this section defines “nar-
cotic drug” to include various substances, including “[c]ocaine, its salts,
optical and geometric isomers, and salts of isomers.” § 802(17).
22 No. 22-2666

section 851 notices as the bases for a statutory enhancement
to Anderson’s sentencing range pursuant to section
841(b)(1)(A). In that briefing, the government conceded that
the 2009 Lake County conviction for attempted possession of
heroin was a misdemeanor and thus did not qualify as a prior
felony drug offense. R. 55 at 2. Anderson also raised questions
about the 2006 and 2013 convictions. The 2006 Lake County
conviction was for possession of cocaine, but Illinois’ defini-
tion of cocaine is broader than the federal definition, in that
the state definition includes positional isomers whereas the
federal definition does not. Compare 720 ILCS 570/206(b)(4)
(effective in relevant part June 1, 2000) with 21 U.S.C. § 812,
Schedule II(a)(4), and §§ 802(14) and (17). Thus, this court
held in United States v. Ruth, 966 F.3d 642, 647–50 (7th Cir.
2020), that because the Illinois definition of cocaine is categor-
ically broader than the federal definition, a 2006 conviction for
cocaine cannot qualify as a felony drug offense that triggers
section 841(b)(1)(A)’s sentencing enhancement. As for the
2013 Peoria conviction for possession of heroin, Anderson ar-
gued that that offense did not qualify as a “prior” conviction
because he was convicted and sentenced in state court on that
offense on March 25, 2013, but the conviction did not become
final until the 30-day period in which to appeal expired on
April 24, 2013. By that time, the heroin-conspiracy offense
charged in this case had already come to an end, given that
Anderson submitted himself to custody and began serving
his sentence on the state conviction on April 9, 2013, and he
had remained in custody continuously after that date. Finally,
apart from these three convictions, the government pointed
out that Anderson had the two other prior felony drug con-
victions from Cook County, Illinois that we mentioned ear-
lier: one for possession of 30–500 grams of cannabis and the
No. 22-2666 23

second for the manufacture/delivery of 1–15 grams of cocaine.
These were both noted in the PSR prepared for Anderson’s
sentencing in this case (and to which the defense did not raise
an objection), but neither of them had been cited in the section
851 notices that the government had filed. For that reason,
Anderson argued that the government could not rely on these
sentences in arguing that Anderson faced a potential manda-
tory life sentence even without the death-results enhance-
ment.
Given the various problems and questions regarding An-
derson’s prior drug convictions, Anderson now contended
that Schneiderheinze was also ineffective for failing to
properly investigate his criminal history to determine
whether that history, alone or in combination with other fac-
tors, exposed Anderson to a potential life term, as the govern-
ment had asserted and Schneiderheinze had assumed. R. 57
at 10–12.
After considering the evidence and briefing, the district
court, without deciding whether Schneiderheinze was inef-
fective in advising Anderson to plead guilty and accept a 20-
year term, concluded that Anderson was not prejudiced by
any shortcomings in her lawyering and denied his section
2255 motion on that basis. R. 59. As the court saw it, Anderson
faced two choices during the plea negotiations: (1) accept the
plea offer, which turned a blind eye to his prior convictions,
and lock in a 20-year sentence, or (2) challenge the death-re-
sults enhancement, surrender the certainty of the sentence
proposed in the plea offer, and risk the possibility that his
eventual sentence might be no better and possibly signifi-
cantly worse. The decision to accept the plea deal amounted
to a strategic choice. There was no guarantee that the
24 No. 22-2666

government would not have withdrawn the plea offer had
Anderson challenged the death-results enhancement. If An-
derson lost the death-results challenge, he would have faced
a mandatory minimum prison term of 20 years; if he lost and
he had one prior felony drug conviction, he faced a manda-
tory prison term of life. Even if he won on the death-results
enhancement, he faced a 20-year minimum term if either of
Heilman’s or Holmes’ overdoses were deemed to have re-
sulted in serious bodily injury. And he still would have faced
a mandatory life term in two other scenarios: (1) he had two
prior felony drug convictions or (2) he had one prior felony
drug conviction and his heroin trafficking had resulted in at
least one instance of serious bodily injury. R. 59 at 8–9.
The district court agreed with Anderson that in order to
accurately evaluate Anderson’s sentencing exposure, his
counsel would have had to undertake at least some inquiry
into his prior convictions to determine whether they qualified
as predicate felony drug convictions under section 802(44)
sufficient to trigger enhanced statutory penalties. There was
no evidence indicating whether or not Schneiderheinze, apart
from looking at the criminal history documentation provided
to her by the probation department and the prosecution and
ascertaining whether her client had any concerns about the
accuracy of those documents, undertook such an investiga-
tion. R. 59 at 10. In retrospect, it was clear that there were
problems with at least one and possibly all three of the prior
convictions that the government had cited in its section 851
notices as the trigger for enhanced statutory penalties: The
government had now stipulated that the 2009 Lake County
conviction was not a felony drug offense, and Anderson was
raising questions as to whether the 2006 Lake County and
2013 Peoria County convictions themselves properly
No. 22-2666 25

qualified as prior felony drug convictions. In the district
court’s view, the question whether Schneiderheinze con-
ducted, at the least, a “cursory investigation” into those three
investigations “weigh[ed] heavily” on the reasonableness of
her advice to Anderson that he forgo further inquiry into the
death-results enhancement and lock in the 20-year sentence
provided for in the plea agreement. R. 59 at 10. “Without prior
predicate offenses, [Anderson] had at least a chance of avoid-
ing a mandatory minimum sentence.” R. 59 at 10. “However,
given the lack of evidence on this point, the Court cannot con-
clusively determine whether counsel’s performance was defi-
cient.” R. 59 at 11.
Instead, the court resolved the matter on the question of
prejudice. Unless Anderson had agreed to the death-results
finding as part of his guilty plea, his only other option was
trial. There was, in Schneiderheinze’s view, ample evidence
to support a guilty verdict on the charge that Anderson had
conspired to distribute at least one kilogram of heroin. R. 59
at 11–12. As for the statutory aggravating factors, even assum-
ing that Anderson could conclusively demonstrate that his
heroin distribution was not a but-for cause of Reader’s
death, 12 there remained other avenues to either a 20-year min-
imum term or a mandatory life sentence. R. 59 at 11. If Ander-
son were convicted, he faced, at the very least, a 20-year

12 Of course, it was the government that would have borne the burden

of proof on this point at trial. Burrage, 571 U.S. at 218–19, 134 S. Ct. at 892.
But we take the district court’s point that for purposes of establishing that
he was prejudiced by his plea counsel’s purported ineffectiveness, it was
Anderson’s burden to show that the government would have been unable
to prove beyond a reasonable doubt that the heroin Anderson distributed
was a but-for cause of Reader’s death.
26 No. 22-2666

minimum term assuming, for example, that the 2006 Lake
County conviction for cocaine possession qualified as a prior
felony drug conviction. R. 59 at 11–12.
The court also rejected Anderson’s effort to retroactively
cast doubt on one of the two prior remaining felony convic-
tions cited in the section 851 notices (the third conviction hav-
ing now been identified as a misdemeanor). The court
acknowledged that Anderson was arguing for the first time
that his 2006 cocaine conviction did not qualify as a felony
drug conviction because Illinois’ definition of cocaine is cate-
gorically broader than the federal definition, and his plea
counsel should have recognized as much. R. 59 at 12 (citing
Ruth, 966 F.3d at 650). But the court was unwilling to recog-
nize this argument for three reasons: (1) Anderson had not
argued in his section 2255 motion that his counsel was inef-
fective for failing to investigate his prior criminal history and
the government thus had not had a chance to respond on that
point. (2) Anderson was arguing that his attorney in 2015
should have made a challenge to the 2006 conviction based on
case law that was not decided until 2020, five years after his
guilty plea. The court agreed it was theoretically possible for
his counsel to have made such a challenge, but given there
was no precedent in 2015 recognizing that Illinois defined co-
caine more broadly than the federal government did, the
court, citing Harris v. United States, 13 F.4th 623, 630–31 (7th
Cir. 2021), found that it was reasonable for Anderson’s coun-
sel to accept the proverbial bird in the hand and to lock in a
20-year sentence rather than risk a mandatory life term. Fi-
nally, (3) Anderson’s section 2255 motion only took into ac-
count the death-results enhancement, not the enhancement
for serious bodily injury. But his plea agreement
No. 22-2666 27

acknowledged that the government could prove the factual
bases for both enhancements. R. 59 at 12–14.
The court thus concluded that Anderson had not shown
that he was prejudiced by any ineffectiveness on the part of
his counsel when she advised him to enter into a plea agree-
ment that capped his sentence at 20 years. The only other op-
tion available to Anderson was to go to trial, which would
have exposed him to a sentence at least as long as, if not longer
than, the 20-year term he had agreed to, and possibly to a
mandatory life sentence. R. 59 at 13–14.
The court issued a certificate of appealability as to the prej-
udice issue. R. 59 at 15.
II.
This case looks substantially different now than it did
when it was last before us. As our procedural summary
makes clear, the premise of Anderson’s section 2255 claim as
initially presented to the district court and to this court was
that the death-results enhancement drove the life sentence
that he was facing without the plea agreement, and that if that
enhancement were taken off the table, then Anderson was fac-
ing a mandatory minimum term of 20 years, not life. That
premise was the springboard for Anderson’s claim that, had
his counsel consulted with a medical expert and exposed the
government’s inability to carry its burden of proof as to the
death-results enhancement, Anderson would have rejected
the plea agreement and taken his chances at trial. Neither in
the district court nor in this court did the government chal-
lenge the premise that the death-results enhancement was the
sole basis for a mandatory term of life in prison. It was against
that backdrop that we concluded in the prior appeal that
28 No. 22-2666

Anderson’s theory of ineffectiveness was plausible and that
an evidentiary hearing was required.
Only on remand did the government argue—consistent
with the more fulsome explanation Schneiderheinze pro-
vided in her testimony as to her reasons for advising Ander-
son to accept the plea deal—that the death-results enhance-
ment was only one of several bases on which Anderson po-
tentially faced a mandatory minimum term of life. Thus, the
government now argued, it was reasonable for his counsel to
negotiate a plea requiring him to serve a term of 20 years
without looking further into the viability of the death-results
enhancement: even assuming the government’s inability to
establish the factual basis for that enhancement, Anderson
was still facing a mandatory life term under either of two al-
ternatives.
The government did not present this line of argument to
us previously, although it appears to have realized that there
was at least one alternative ground on which Anderson faced
a mandatory life term: When it set forth the statutory scheme
in its brief, the government did briefly acknowledge, in a foot-
note, that responsibility for a serious bodily injury plus one
prior felony drug conviction would also trigger a mandatory
term of life in prison. See ante at 16 n.8. It noted the same at
oral argument in response to a question from a member of this
court. Appeal No. 19-1257, Oral Arg. 10-29-2020 at 23:40–
24:44. Yet, inexplicably, at no point did the government chal-
lenge the premise of Anderson’s claim that the death-results
enhancement was crucial to a life term and without it he
would have faced, at worst, a minimum term of 20 years. In-
stead, the government pressed the theory that even in the face
of a 20-year minimum, it was reasonable for Anderson’s
No. 22-2666 29

counsel to negotiate the plea terms that she did without con-
sulting a medical expert as to the cause of Reader’s death and
that Anderson could not show that he was prejudiced by any
ineffectiveness on her part in doing so. That theory, of course,
did not carry the day in the prior appeal.13
Nonetheless, we will entertain the government’s belated
argument as to prejudice. Schneiderheinze’s testimony on re-
mand makes plain that the alternative bases for a mandatory
life term factored into her thinking as to the benefits the 20-
year plea bargain would confer on her client. The govern-
ment’s counsel in turn raised these alternatives at the hearing
on remand. Both parties had at least some ability to lay out
their positions as to these alternatives at the hearing, and the
district court in turn addressed them in its decision. At no
point in the course of the remand did Anderson argue that the
government had waived its belated invocation of alternative
pathways to a life term as a basis for finding that he was not
prejudiced. See United States v. Buncich, 20 F.4th 1167, 1172
(7th Cir. 2021) (although “[a]s a general rule, a party may not
use the accident of a remand to make an argument that he
could have raised—but did not—in his first appeal[,] [t]hat
general rule does not hold true … when the opposing party
fails to make a waiver argument in the district court and in-
stead responds on the merits”) (citations and internal quota-
tion marks omitted); United States v. Morgan, 384 F.3d 439, 443
(7th Cir. 2004) (“[a] waiver argument … can be waived by the
party it would help”).

13 To the extent the district court’s opinion on remand relies in part on

a similar rationale, it appears to have overlooked the reasoning in our
prior opinion.
30 No. 22-2666

For the reasons discussed below, in view of the serious
bodily injuries suffered by the two individuals who over-
dosed on heroin supplied by Anderson, we agree with the
district court’s bottom-line conclusion that he was not preju-
diced by any ineffectiveness on the part of his plea counsel.
Coupled with one prior felony drug conviction, those injuries
would also have triggered a mandatory term of life in prison.
§ 841(b)(1)(A). Although, as it turns out, most of Anderson’s
prior drug convictions do not qualify as prior felony drug
convictions under section 802(44) for purposes of the statu-
tory penalty enhancement, including all three of the convic-
tions that the government cited in its section 851 notices, there
is one conviction in his criminal history that indisputably
does so qualify. Therefore, there was a viable, alternative
ground on which Anderson would have been subject to a life
term. We have no reason to doubt, given the seriousness of
the offense and Anderson’s criminal history that the govern-
ment would have pursued that alternative had Anderson not
accepted the plea agreement.
We review the district court’s decision to deny Anderson’s
request for relief pursuant to section 2255 de novo. E.g., Elion
v. United States, 76 F.4th 620, 626 (7th Cir. 2023).
Like any other criminal defendant, Anderson had a Sixth
Amendment right to the effective assistance of counsel. Lee,
582 U.S. at 363, 137 S. Ct. at 1964. In order to obtain relief on
his claim that his counsel was ineffective, Anderson must
show both that his counsel’s performance was deficient and
that he was prejudiced as a result. Strickland v. Washington, 466
U.S 668, 687, 104 S. Ct. 2052, 2064 (1984). To establish deficient
performance, he must show that his counsel’s conduct “fell
below an objective standard of reasonableness.” Id. at 688, 104
No. 22-2666 31

S. Ct. at 2064. To establish prejudice, he must demonstrate a
“reasonable probability that, but for counsel’s unprofessional
errors, the result of the proceeding would have been differ-
ent.” Id. at 694, 104 S. Ct. at 2068.
“Judicial scrutiny of counsel’s performance must be
highly deferential.” Strickland, 466 U.S. at 689, 104 S. Ct. at
2065. Our review must take account of the “wide range of rea-
sonable professional assistance” that will comport with the
Sixth Amendment’s guarantee of the right to counsel. Ibid.
“[C]ounsel’s representation need not be perfect, indeed not
even very good, to be constitutionally adequate.” Delatorre v.
United States, 847 F.3d 837, 845 (7th Cir. 2017) (internal quota-
tion marks and citations omitted). We must evaluate the ade-
quacy of counsel’s performance from her perspective at the
time she represented the petitioner, starting from a presump-
tion that her representation was adequate. Strickland, 466 U.S.
at 689, 104 S. Ct. at 2065.
The right to effective representation extends, of course, to
the plea-negotiation process. Lafler v. Cooper, 566 U.S. 156, 162,
132 S. Ct. 1376, 1384 (2012) (collecting cases). A plea that is the
product of ineffective assistance of counsel cannot be consid-
ered knowing or voluntary. United States v. Harper, 934 F.3d
524, 529 (7th Cir. 2019) (citing Hurlow v. United States, 726 F.3d
958, 967 (7th Cir. 2013)). To establish prejudice in the plea-bar-
gaining context, Anderson must show that “the outcome of
the plea process would have been different with competent
advice.” Lafler, 566 U.S. at 163, 132 S. Ct. at 1384 (citing Mis-
souri v. Frye, 566 U.S. 134, 148, 132 S. Ct. 1399, 1410 (2012). One
way for him to show this is to demonstrate that “but for coun-
sel’s errors, he would not have pleaded guilty and would
32 No. 22-2666

have insisted on going to trial.” Hill, 474 U.S. at 59, 106 S. Ct.
at 370; see also Lafler, 566 U.S. at 163, 132 S. Ct. at 1384–85.
As we noted in the prior appeal, “[i]n the plea bargaining
context, reasonably competent counsel will attempt to learn
all of the facts of the case, make an estimate of a likely sen-
tence, and communicate the results of that analysis before al-
lowing [her] client to plead guilty.” Anderson I, 981 F.3d at 573
(citing Gaylord v. United States, 829 F.3d 500, 506 (7th Cir.
2016)); see also Bridges v. United States, 991 F.3d 793, 803 (7th
Cir. 2021); Brock-Miller v. United States, supra, 887 F.3d at 308
(collecting cases). As in any case, an attorney must “make rea-
sonable investigations or … make a reasonable decision that
makes particular investigations unnecessary.” Strickland, 466
U.S. at 691, 104 S. Ct. at 2066. “[A] particular decision not to
investigate must be directly assessed for reasonableness in all
the circumstances, applying a heavy measure of deference to
counsel’s judgments.” Id., 104 S. Ct. at 2066. “[S]trategic
choices made after less than complete investigation are rea-
sonable precisely to the extent that reasonable professional
judgments support the limitations on investigation.” Id. at
690–91, 104 S. Ct. at 2066.
It is against this legal backdrop that we address Ander-
son’s claim that his counsel was ineffective in negotiating the
plea agreement and recommending that he accept it. The core
premise of Anderson’s claim is that Schneiderheinze could
not properly advise him to accept the plea agreement without
first consulting with a toxicology expert in order to evaluate
the viability of the death-results enhancement. Dr. Aks’ testi-
mony makes sufficiently clear in hindsight that the govern-
ment would not, in fact, have been able to prove beyond a
reasonable doubt that the heroin Anderson distributed to
No. 22-2666 33

Reader via Mansini was a but-for cause of Reader’s death—
the government certainly makes no argument to the contrary.
See also R. 59 at 10–11. Thus, Anderson reasons, had Schnei-
derheinze herself spoken with an expert, she would have re-
alized the same thing, advised him accordingly, and, being
properly counseled as to the shaky foundation for the death-
results enhancement, he would have rejected the plea agree-
ment and gone to trial.
Schneiderheinze, of course, justified her decision not to
consult with a toxicologist by pointing out that because there
were two other pathways to a life sentence for Anderson, it
was reasonable for her not to delve further into the strength
of the factual basis for the death-results enhancement. As
Schneiderheinze recounts events, she and her client both ap-
preciated the potential weaknesses of the government’s case
as to this enhancement, but she made a reasonable calcula-
tion, given that a life sentence would remain on the table even
absent the death-results enhancement, that it was better to ac-
cept a plea for an agreed-upon term of 20 years rather than
engaging a medical expert with the aim of opposing the gov-
ernment’s insistence that Anderson was responsible for
Reader’s death and should so acknowledge in the plea agree-
ment.
Of course, this rationale assumes the validity of the alter-
nate grounds for a life sentence. Specifically, it assumes that
Anderson had at least one qualifying prior felony drug con-
viction, which in combination with a serious bodily injury
would trigger a life term, or that Anderson had two qualify-
ing prior felony drug convictions, which in and of themselves
would mandate a life term.
34 No. 22-2666

This is what led Anderson to argue on remand, as he does
here, that Schneiderheinze was also ineffective for failing to
investigate his criminal history. In retrospect, as we explain
below, all three of the convictions that the government in-
tended to rely on to trigger enhanced statutory penalties do
not qualify as predicate felony drug convictions under section
802(44), and as Anderson sees things, Schneiderheinze would
have come to this realization had she made a reasonable effort
to evaluate these three convictions.
Before we proceed any further on this subject, we must
deal with a threshold question. The district court posited that
Anderson had waived any claim of ineffectiveness as to his
criminal history because he did not raise such a claim in his
habeas petition or in the initial round of litigation. The gov-
ernment makes the same assertion on appeal.
But, in the first instance, this rationale overlooks the gov-
ernment’s own belated reliance on the alternate pathways to
a life sentence, both of which depend on Anderson having ei-
ther one or two qualifying predicate convictions. 14 Schneider-
heinze in her own testimony cited these alternative pathways
as the reason why she did not think it necessary to look fur-
ther into the merits of the death-results enhancement. Ander-
son has the right to respond to the government’s invocation

14 The government adds that the certificate of appealability does not

include a claim that Schneiderheinze was ineffective for failing to investi-
gate Anderson’s criminal history. Of course, we have the authority to ex-
pand the certificate, see Stechnauer v. Smith, 852 F.3d 708, 717–18 (7th Cir.
2018); Welch v. Hepp, 793 F.3d 734, 737–38 (7th Cir. 2015); Rittenhouse v.
Battles, 263 F.3d 689, 693 (7th Cir. 2001), and we could do so here if it were
necessary to resolve the appeal. We do not find it to be necessary in this
case.
No. 22-2666 35

of these alternate pathways, and his response appropriately
includes an argument that his plea counsel could not have
reasonably relied on those alternatives without being confi-
dent that they were viable, which in turn presumes that his
criminal history would support one or both of the alterna-
tives. Properly understood, Anderson’s argument that
Schneiderheinze was ineffective in this respect is not a sepa-
rate claim but one intertwined with his contention that his
counsel’s advice to accept the plea deal and stipulate to hav-
ing caused Reader’s death without first consulting with a
medical expert amounted to ineffective assistance. As the dis-
trict court itself recognized, “Under the circumstances of this
case a cursory investigation into, at a minimum, the three …
convictions that were identified in the § 851 information filed
by the government weighs heavily on the reasonableness of
Petitioner’s attorney’s advice to forgo an investigation into
the applicability of the death enhancement and secure the
guaranteed 20-year sentence offered by the [plea] agree-
ment.” R. 59 at 10.
Second, the duty to confirm that each of the prior convic-
tions cited in the section 851 notices qualified as a valid pred-
icate did not belong to Schneiderheinze alone. These were the
convictions that the government itself had selected from An-
derson’s criminal history as the bases for a statutory enhance-
ment to his prospective sentence. As officers of the court,
counsel for Anderson and the government both had an obli-
gation to confirm that these convictions qualified as predicate
felony drug convictions for sentencing purposes. Yet the rec-
ord rather strongly suggests that even as the evidentiary hear-
ing opened in March 2022, more than eight years after the first
section 851 notice was filed and six years after Anderson was
sentenced, neither Schneiderheinze nor the government’s
36 No. 22-2666

counsel had any idea that there were potential problems with
these convictions: When the government cross-examined
Schneiderheinze during the hearing, it walked her through
each of the three convictions cited in its section 851 notices
and elicited her agreement that each qualified as a valid pred-
icate felony drug offense. See R. 52 at 172–75. Only in the post-
hearing briefing, as we have noted, did the government’s
counsel acknowledge that there was a problem with at least
one of these convictions. Of course, we recognize that the
overlooked flaws may be actionable only by way of an inef-
fectiveness claim that would assign the blame to Anderson’s
counsel for not detecting the problems before he pled guilty.
Our point, however, is that there is blame to be shared for the
eleventh hour at which these flaws have been noticed and ad-
dressed. And under all of the circumstances of this case, we
do not believe that Anderson should be precluded from rais-
ing them.
Third, even if we were inclined to deem Anderson fore-
closed from pursuing a claim of ineffectiveness with respect
to his criminal history, any shortcomings in his prior drug
convictions as predicates for enhanced statutory penalties
would remain relevant as to any prejudice he suffered vis-à-
vis his counsel’s alleged ineffectiveness as to the death-results
enhancement. The district court itself resolved Anderson’s
claim with respect to the death-results enhancement on the
question of prejudice, and the government urges us to do the
same. We will likewise focus on the prejudice component of
Anderson’s case and consider the various problems with his
prior drug convictions in that context.
Where, as here, the government relies on one or more of a
defendant’s prior convictions to trigger an enhanced statutory
No. 22-2666 37

penalty, section 851 requires that it file an information (what
we refer to as a “notice”) identifying the relevant conviction
or convictions. The two separate notices that the government
filed (eight months apart) in this case both cited the same
three Illinois convictions: the 2006 conviction for possession
of cocaine; the 2009 conviction for attempted possession of
heroin; and the 2013 conviction for unlawful possession of
heroin.
The 2009 Lake County conviction for attempted posses-
sion of heroin 15 turns out to have been a conviction for a mis-
demeanor offense with a maximum penalty of a year or less
in prison, as the parties now agree. It therefore does not qual-
ify as a predicate felony drug conviction. See § 802(44) (“fel-
ony drug offense” means, inter alia, “an offense that is punish-
able by imprisonment for more than one year”); Burgess v.
United States, 553 U.S. 124, 129–30, 128 S. Ct. 1572, 1577 (2008);
United States v. Elder, 840 F.3d 455, 461–62 (7th Cir. 2016).
The 2013 Peoria County conviction for possession of her-
oin was not yet final 16 on April 9, 2013, when Anderson’s ac-
tive participation in the charged federal conspiracy ended
with his incarceration on the state offense; although the circuit
court had entered judgment on his conviction on March 25,
2013, the 30-day window for him to take a direct appeal of the

15 The PSR noted and the district court acknowledged that this con-

viction was for attempted heroin possession that constituted relevant con-
duct vis-à-vis the federal offense. See U.S.S.G. § 1B1.3. R. 111 at 15, 30 (Re-
vised PSR ¶¶ 65, 157); R. 126 at 23.
16 Section 841(b)(1)(B) makes clear that the triggering event for a re-

cidivist enhancement is the defendant’s commission of a controlled-sub-
stance offense “after a prior offense for a felony drug offense has become
final[.]”
38 No. 22-2666

conviction had not yet run, and so the conviction does not
qualify as a final, “prior” conviction vis-á-vis the federal of-
fense. Although we have not previously addressed this par-
ticular issue, at least nine other circuits have so held in a line
of authority originating more than 40 years ago. See United
States v. Lovell, 16 F.3d 494, 497 (2d Cir. 1994); United States v.
Allen, 566 F.2d 1193, 1195 (3d Cir. 1977); United States v. Camp-
bell, 980 F.2d 245, 251 n.9 (4th Cir. 1992); United States v. Mo-
rales, 854 F.2d 65, 69 (5th Cir. 1988); United States v. Walker, 160
F.3d 1078, 1093 (6th Cir. 1998); United States v. Maxon, 339 F.3d
656, 659 (8th Cir. 2003); Williams v. United States, 651 F.2d 648,
650–51 (9th Cir. 1981); United States v. Short, 947 F.2d 1445,
1460 (10th Cir. 1991); United States v. Lippner, 676 F.2d 456, 467
(11th Cir. 1982). This well-established line of authority would
have been readily discoverable to an attorney looking into the
finality question. The government has cited no contrary au-
thority, 17 nor has it given us any reason to depart from the
holdings of our sister circuits, and we now follow those deci-
sions in holding that Anderson’s 2013 conviction was not yet
final and therefore was not a “prior” conviction for sentencing
purposes in this case.
This brings us to the 2006 Lake County conviction for co-
caine possession. Under the law of this circuit as it exists to-
day, that conviction of course would not qualify as a predicate
felony drug conviction given Ruth’s holding as to the

17 Our decision in United States v. Garcia, 32 F.3d 1017, 1018–20 (7th

Cir. 1994), on which the government relies, is not to the contrary. Garcia
deals with the factual overlap between a federal conspiracy offense of con-
viction and a prior state narcotics conviction rather than the finality of the
prior conviction. Nothing that the decision says in that regard is incon-
sistent with the finality principle that other circuits have adopted.
No. 22-2666 39

categorical mismatch between the Illinois and federal defini-
tions of “cocaine.” 966 F.3d at 647–50. Because we are focusing
on prejudice rather than ineffectiveness, we can set aside the
question whether Schneiderheinze should have considered
making a Ruth-type challenge to the 2006 conviction. But even
for the limited purpose of assessing prejudice, it bears men-
tion that our recent decision in Coleman v. United States, 79
F.4th 822 (7th Cir. 2023), concludes that the precedential tools
were in place in 2015 for a Ruth-type challenge to be made to
this type of conviction. We held in Coleman—over a dissent—
that it would have been unreasonable in 2014 for a defend-
ant’s attorney not to have even considered a categorical chal-
lenge to the government’s reliance on his prior Illinois cocaine
convictions to enhance his sentence, particularly where the
enhancement would have resulted in a life term. Id. at 832. We
noted:
[T]he groundwork for such an argument was, at
the very least, foreshadowed by numerous de-
cisions issued before 2014 (the year Coleman
was sentenced) that applied the categorical ap-
proach to predicate offenses in other contexts.
These cases demonstrate that, although the cat-
egorical approach had not yet been applied to
prior convictions like Coleman’s by 2014, the
framework for making such a challenge had
been established.
Id. at 831–32 (citations omitted). We can therefore assume that
had a categorical challenge been made to the government’s
reliance on a prior Illinois cocaine conviction in 2015, it ulti-
mately would have been successful in eliminating the last of
the three prior drug convictions that the government had
40 No. 22-2666

cited as the basis for statutory enhancements to Anderson’s
sentence. See id. at 833 & n.10.
Of course, there were two other prior felony drug convic-
tions in Anderson’s criminal history—the two Cook County
convictions in the year 2000, one for the manufacture/delivery
of 1–15 grams of cocaine and the other for possession of 30–
500 grams of cannabis. Although the government had not
cited either of these convictions in its two section 851 notices,
it was free to file an amended notice at any time prior to the
entry of Anderson’s guilty plea. See § 851(a)(1). Filing an
amended section 851 notice is neither unprecedented nor un-
usual, and we have no reason to doubt that had Anderson’s
counsel challenged the sufficiency of the convictions cited in
its prior notices, the government would have identified the
additional convictions in Anderson’s criminal history and
filed an amended notice incorporating those convictions. We
can therefore consider whether either or both of these prior
convictions would have constituted valid predicates under
section 802(44) for purposes of enhancing Anderson’s statu-
tory sentencing range.
The conviction for the manufacture and/or delivery of 1-15
grams of cocaine obviously runs into the same Ruth categori-
cal mismatch problem that the 2006 Lake County conviction
for cocaine possession does. So it would not have supported
a statutory sentence enhancement.
The conviction for possession of 30–500 grams of cannabis,
however, is another matter. It does not present a Ruth mis-
match problem, it was a felony conviction, and the conviction
was final long before Anderson’s participation in the heroin
trafficking at issue in this case concluded. The conviction does
qualify as a valid predicate under section 802(44) and would
No. 22-2666 41

support a statutory sentence enhancement under section
841(b)(1)(A). 18
With just a single conviction in Anderson’s criminal his-
tory qualifying as a valid prior felony drug conviction, how-
ever, it is apparent that one of the two alternative pathways
to a mandatory life term—having previously been convicted
of two such felony drug convictions—was closed. The remain-
ing ground for a life term would have been that Anderson
distributed heroin resulting in serious bodily injury and that
he had one prior felony drug conviction. § 841(b)(1)(A).
Anderson, of course, stipulated in pleading guilty that he
was responsible for serious bodily injuries to both Heilman
and Holmes, and in contrast with his stipulation to having
caused Reader’s death, we have no reason to question the va-
lidity of that stipulation. Recall that these two individuals
overdosed (in Heilman’s case, twice) on heroin that was pur-
portedly supplied by Anderson and required resuscitation.
Those overdoses do not present the same causation issues that
Reader’s death presents. It is possible that Holmes’ overdose
might present a source question in that the heroin was ob-
tained via Mansini, and the record reflects that Anderson was
Mansini’s “primary” (not exclusive) supplier of heroin at that
particular time. R. 111 at 7 (Revised PSR ¶ 30). But there is no
such question presented as to Heilman’s second overdose,

18 Illinois has since decriminalized the simple possession of up to 30

grams of marijuana by Illinois residents. See 410 ILCS 705/10-10(a)(1). But
that is irrelevant for purposes of section 841. See United States v. Sanders,
909 F.3d 895, 899–904 (7th Cir. 2018) (subsequent re-classification of prior
state felony drug conviction to a misdemeanor offense does not preclude
application of section 841 recidivist enhancement).
42 No. 22-2666

which occurred after she ingested heroin she had obtained di-
rectly from Anderson. R. 111 at 6 (Revised PSR ¶¶ 28–29).
The principal point that Anderson has raised with respect
to the serious-bodily-injury enhancement is that there existed
little case law in 2015 speaking to the question whether an
overdose from which one has recovered qualifies as a serious
bodily injury. It is true enough that most of the cases address-
ing this question (and which answer it in the affirmative)
post-date Anderson’s guilty plea. See, e.g., United States v.
Cooper, 990 F.3d 576, 582–83 (8th Cir. 2021); United States v.
Seay, 2023 WL 171148, at *5 (S.D. Ohio Jan. 12, 2023); United
States v. Coles, 2022 WL 17405830, at *12–*13 (M.D. Pa. Dec. 2,
2022); United States v. Piaquadio, 2019 WL 3337063, at *5 (M.D.
Pa. July 25, 2019); Cockrell v. United States, 2016 WL 11190470,
at *6–*7 (E.D. Tex. Oct. 18, 2016), report & recommendation
adopted, 2017 WL 1088339 (E.D. Tex. Mar. 22, 2017), j. aff’d, 769
F. App’x 116 (5th Cir. 2019) (non-precedential decision). 19 But
the statute itself defines “serious bodily injury” as a bodily
injury which, inter alia, involves “a substantial risk of death.”
21 U.S.C. § 802(25)(A). 20 It is hard to imagine why the over-
doses that Heilman and Holmes experienced would not meet

19 Schneiderheinze cited the lack of substantial pre-plea precedent on

this point as a reason why she testified in her deposition that she did not
take the prospect of the serious bodily injury enhancement seriously. R. 59
at 150–52.
20 The statute does not define “bodily injury,” but that term is fre-

quently understood to include the impairment of bodily and mental func-
tions. See United States v. Breshers, 684 F.3d 699, 702–03 (7th Cir. 2012) (cit-
ing, inter alia, 18 U.S.C. § 1365(h)(4)(D)); United States v. Myers, 972 F.2d
1566, 1572–73 (11th Cir. 1992) (citing multiple other federal statutes).
No. 22-2666 43

that definition, when each necessitated the administration of
either CPR or Narcan®.
The district court found little reason to believe that the jury
would have acquitted Anderson on the charge that he con-
spired to distribute in excess of one kilogram of heroin, and
we likewise have no reason to believe that the jury would
have acquitted him of distributing heroin that resulted in se-
rious bodily injury. Two people who ingested heroin supplied
by Anderson overdosed on three occasions, requiring active
intervention with CPR or Narcan® to revive them. This meets
the statutory definition of “serious bodily injury,” and we
have no reason to doubt that a jury would have so found.
Thus, even assuming that Anderson’s plea counsel was in-
effective in one or more respects in advising him to enter into
the plea agreement, we agree with the district court’s conclu-
sion that he was not prejudiced. A guilty finding on the seri-
ous bodily injury enhancement, coupled with his 2000 convic-
tion for possessing 30–500 grams of cannabis, would have
triggered a mandatory term of life in prison. By comparison,
the 20-year term specified by the plea agreement was much
less onerous.
This is not to say that there were not serious omissions by
attorneys on both sides of this prosecution. In negotiating the
plea agreement, both prosecution and defense counsel oper-
ated on the assumption that there were three viable pathways
to a mandatory life term. But serious questions as to Ander-
son’s criminal history, which was a gateway to all three of
these paths, were overlooked. Although the categorical mis-
match problem with two of Anderson’s prior drug convic-
tions are much more clear in retrospect than they would have
been at the time of the plea, the fact that one prior conviction
44 No. 22-2666

was for a misdemeanor and the other was not yet final when
Anderson was taken into custody and his participation in the
charged federal conspiracy came to an end would have been
readily discernible had counsel made modest efforts to in-
quire beyond the face of the convictions. A defendant has a
right, and the court has a right, to expect that counsel for both
parties will have taken the steps necessary to confirm that his
prior convictions meet the statutory criteria to qualify as prior
felony drug convictions, especially when those convictions
are cited as the basis for enhanced statutory minimum and
maximum prison terms. We should not have to be sorting out
such issues years after the defendant has been convicted and
sentenced.
We are also more than a little dismayed that the govern-
ment did not rely on the alternative pathways to a life term in
the prior appeal when it argued that Anderson was not prej-
udiced by any ineffectiveness on the part of his plea counsel.
The issue of prejudice was obviously ripe for consideration at
that time, and the government made other arguments as to
prejudice. The alternative grounds for a life sentence were ob-
viously within the knowledge and contemplation of the gov-
ernment as the plaintiff in this prosecution. Had this line of
argument been raised at that time, we might not have found
it necessary to remand this case for an evidentiary hearing on
the death-results enhancement.
III.
For all of the reasons we have discussed, Anderson was
not prejudiced by any ineffectiveness on the part of his plea
counsel. He is therefore not entitled to relief on his claim of
attorney ineffectiveness. We AFFIRM the district court’s judg-
ment.