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 ineffective assistance. Specifically, Anderson asserts that his 

counsel advised him to plead guilty to conspiring to distribute 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 heroin 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 mandatory 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 attorney ineffectiveness and remanded for an evidentiary hearing. See Anderson v. United States, 981 F.3d 565, 577–78 (7th Cir. 

2020) (“Anderson I”). 

Based on the testimony presented at that hearing, Anderson has now shown that consultation with a toxicology expert 

would have revealed the government’s inability to prove beyond 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 mandatory 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, Anderson 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 enhancement, such that Anderson was not prejudiced by his 

counsel’s failure to consult with a toxicologist. This line of argument 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 mandatory 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 Anderson 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 enhancement, 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 estimated conservatively that Anderson’s overt acts in furtherance 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 indicated 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 ingested 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 effects of any other drugs in Reader’s system. In junior and senior 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 resolved 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 according 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 September and early November 2012, two other individuals overdosed 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 quantities 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 Anderson. Holmes was revived with cardio-pulmonary resuscitation (“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 conspiracy 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 government 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 possession of cocaine; a 2009 conviction in Lake County for attempted possession of heroin; and a 2013 conviction in Peoria 

County, Illinois for unlawful possession of heroin. Additionally, there were two other felony drug convictions in Anderson’s criminal history not included in the section 851 notices 

that potentially might qualify as predicates sufficient to trigger 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 cocaine. 

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 mandatory 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 Anderson 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 minimum 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 Anderson in August 2014, the district court appointed attorney 

Michelle N. Schneiderheinze to represent Anderson pursuant 

to the Criminal Justice Act. Schneiderheinze represented Anderson 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 statements 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 government’s case on the latter point. However, in the course of 

negotiating the plea, the prosecutor was adamant that Anderson 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 sentence of life if he proceeded to trial even if he ultimately prevailed 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 straightforward as the plea agreement made them out to be, but for purposes of his plea he would not dispute that his heroin distribution 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 officer 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 during 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 (Revised 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) agreement, 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 addition 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 Anderson 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 conduct vis-á-vis the federal conspiracy, for a total of 223 months.

Not long after he was sentenced, Anderson began to rethink 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 pursue. 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 voluntary because he received ineffective assistance of counsel in 

connection with the plea decision and that but for his attorney’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 reasonable 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 adequately investigate the cause of Reader’s death. Had she done 

so, he contended, she would have realized that the government 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 Anderson’s section 2255 motion. Among other points, the court directed Schneiderheinze to discuss what advice she had given 

Anderson regarding the death-results enhancement. R. 13. 

On that point, the narrow affidavit that Schneiderheinze prepared 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 hiring a medical expert; and (4) Schneiderheinze was not trained 

to interpret the Reader toxicology results and had not discussed those results with anyone who had such training, so

she could not assess the validity of Anderson’s doubts regarding 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, Schneiderheinze 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 Anderson’s change-of-plea hearing, the judge was satisfied that Anderson 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 denied Anderson a certificate of appealability, see 28 U.S.C. 

§ 2253(c), this court granted him such a certificate and appointed counsel to represent him on appeal.

As Anderson framed his ineffectiveness claim in that appeal, it was the death-results enhancement that drove the prospective 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 Schneiderheinze 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 enhancement, 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 aggravating 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 prejudice 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 enhancement—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 favorable than the sentence the defendant ultimately received pursuant to a 

blind guilty plea. The petitioner in Brock-Miller alleged that had her counsel 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 accepted 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 sentencing 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 attorney’s part in failing to consult with a medical expert regarding 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-injury enhancement or another path to a life term as a reason why any ineffectiveness 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 assistance 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 enhancement: specifically, she had not consulted with a toxicologist or other medical expert. We accepted the premise of Anderson’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 accepting the plea agreement, and we agreed with him that he had 

made a sufficient preliminary showing of prejudice in this regard to warrant a hearing. Specifically, Anderson alleged that 

absent the death-results enhancement, he was facing a Sentencing Guidelines range that might have been as low as 168 

to 210 months’ imprisonment, whereas with the enhancement, 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 objections 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 sentence of at least 20 years and possibly up to life. We said that 

argument “misses the mark.” Id. We explained that the relevant 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 favor of going to trial but for his attorney’s deficiencies. 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 petition, however, questions the government’s 

ability to prove that basis. Without the enhancement, 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). Confronted with such similar sentencing consequences, 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.” Accordingly, 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 opinion. 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 enhancement. 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 reasoned that even if Anderson would face the same or a somewhat 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 remand. Schneiderheinze testified that, under the circumstances, 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 Burrage, 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 issue—indeed, she assumed that her client might have prevailed on a challenge to this enhancement had she and Anderson decided to pursue it—but the government would not 

drop it and would not agree to a term of 20 years unless Anderson acknowledged that his heroin distribution had resulted in Reader’s death. She also understood that the government had other ways of triggering a mandatory minimum 

term of life, whether by showing that Anderson was responsible 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 convictions. In view of those alternatives, Schneiderheinze did not 

believe it was necessary to consult with an expert before advising her client to accept the plea deal and stipulate to responsibility 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 believe her former client’s waiver of attorney-client privilege extended beyond that enhancement, so she had limited her affidavit 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 revealed 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 police 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 contents of the vomitus. Reader also had a prescription for Suboxone® to treat opioid abuse. Suboxone®, by preventing someone 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 prejudice and specifically whether, absent the death-results enhancement, Anderson would have faced a statutorily-mandated term of life in prison in view of the serious bodily injuries 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 depressant or stimulant substances.” Elsewhere, this section defines “narcotic 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’ definition 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 categorically 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 argued 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 convictions from Cook County, Illinois that we mentioned earlier: 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 mandatory life sentence even without the death-results enhancement.

Given the various problems and questions regarding Anderson’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 factors, exposed Anderson to a potential life term, as the government 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 ineffective 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-results 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 significantly 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 Anderson 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 mandatory 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 resulted 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 investigation. 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 conducted, 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 avoiding a mandatory minimum sentence.” R. 59 at 10. “However, 

given the lack of evidence on this point, the Court cannot conclusively determine whether counsel’s performance was deficient.” 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 assuming 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 minimum term or a mandatory life sentence. R. 59 at 11. If Anderson 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 convictions cited in the section 851 notices (the third conviction having 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 categorically 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 recognize this argument for three reasons: (1) Anderson had not 

argued in his section 2255 motion that his counsel was ineffective 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 cocaine 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 counsel to accept the proverbial bird in the hand and to lock in a 

20-year sentence rather than risk a mandatory life term. Finally, (3) Anderson’s section 2255 motion only took into account 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 agreement that capped his sentence at 20 years. The only other option 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 prejudice 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 facing 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 challenge 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 provided in her testimony as to her reasons for advising Anderson to accept the plea deal—that the death-results enhancement was only one of several bases on which Anderson potentially 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 alternatives.

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 footnote, 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 challenge 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. Instead, 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 consulting 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 remand 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 government’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 instead responds on the merits”) (citations and internal quotation 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 overdosed on heroin supplied by Anderson, we agree with the 

district court’s bottom-line conclusion that he was not prejudiced 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 statutory penalty enhancement, including all three of the convictions 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 government 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 different.” 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 reasonable 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 quotation marks and citations omitted). We must evaluate the adequacy of counsel’s performance from her perspective at the 

time she represented the petitioner, starting from a presumption 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 considered 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-bargaining 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 Missouri 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 counsel’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 sentence, and communicate the results of that analysis before allowing [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 reasonable 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 reasonable 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 Anderson’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’ testimony makes sufficiently clear in hindsight that the government 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 Schneiderheinze herself spoken with an expert, she would have realized the same thing, advised him accordingly, and, being 

properly counseled as to the shaky foundation for the deathresults enhancement, he would have rejected the plea agreement 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 appreciated the potential weaknesses of the government’s case 

as to this enhancement, but she made a reasonable calculation, given that a life sentence would remain on the table even 

absent the death-results enhancement, that it was better to accept a plea for an agreed-upon term of 20 years rather than 

engaging a medical expert with the aim of opposing the government’s insistence that Anderson was responsible for 

Reader’s death and should so acknowledge in the plea agreement.

Of course, this rationale assumes the validity of the alternate grounds for a life sentence. Specifically, it assumes that 

Anderson had at least one qualifying prior felony drug conviction, which in combination with a serious bodily injury 

would trigger a life term, or that Anderson had two qualifying 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 intended 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 government makes the same assertion on appeal. 

But, in the first instance, this rationale overlooks the government’s own belated reliance on the alternate pathways to 

a life sentence, both of which depend on Anderson having either one or two qualifying predicate convictions.14 Schneiderheinze in her own testimony cited these alternative pathways 

as the reason why she did not think it necessary to look further into the merits of the death-results enhancement. Anderson 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 investigate Anderson’s criminal history. Of course, we have the authority to expand 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 confident that they were viable, which in turn presumes that his 

criminal history would support one or both of the alternatives. Properly understood, Anderson’s argument that 

Schneiderheinze was ineffective in this respect is not a separate claim but one intertwined with his contention that his 

counsel’s advice to accept the plea deal and stipulate to having caused Reader’s death without first consulting with a 

medical expert amounted to ineffective assistance. As the district 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] agreement.” R. 59 at 10. 

Second, the duty to confirm that each of the prior convictions cited in the section 851 notices qualified as a valid predicate did not belong to Schneiderheinze alone. These were the 

convictions that the government itself had selected from Anderson’s criminal history as the bases for a statutory enhancement to his prospective sentence. As officers of the court, 

counsel for Anderson and the government both had an obligation to confirm that these convictions qualified as predicate 

felony drug convictions for sentencing purposes. Yet the record rather strongly suggests that even as the evidentiary hearing 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 predicate felony drug offense. See R. 52 at 172–75. Only in the posthearing 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 ineffectiveness 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 addressed. And under all of the circumstances of this case, we 

do not believe that Anderson should be precluded from raising them.

Third, even if we were inclined to deem Anderson foreclosed 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-àvis 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 possession of heroin15 turns out to have been a conviction for a misdemeanor offense with a maximum penalty of a year or less 

in prison, as the parties now agree. It therefore does not qualify as a predicate felony drug conviction. See § 802(44) (“felony drug offense” means, inter alia, “an offense that is punishable 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 heroin was not yet final16 on April 9, 2013, when Anderson’s active 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 conviction was for attempted heroin possession that constituted relevant conduct vis-à-vis the federal offense. See U.S.S.G. § 1B1.3. R. 111 at 15, 30 (Revised PSR ¶¶ 65, 157); R. 126 at 23.

16 Section 841(b)(1)(B) makes clear that the triggering event for a recidivist enhancement is the defendant’s commission of a controlled-substance 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 offense. Although we have not previously addressed this particular 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. Campbell, 980 F.2d 245, 251 n.9 (4th Cir. 1992); United States v. Morales, 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 authority, 17 nor has it given us any reason to depart from the 

holdings of our sister circuits, and we now follow those decisions 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 cocaine possession. Under the law of this circuit as it exists today, 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 conviction and a prior state narcotics conviction rather than the finality of the 

prior conviction. Nothing that the decision says in that regard is inconsistent with the finality principle that other circuits have adopted. 
No. 22-2666 39

categorical mismatch between the Illinois and federal definitions 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 mention 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 defendant’s attorney not to have even considered a categorical challenge 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 decisions issued before 2014 (the year Coleman 

was sentenced) that applied the categorical approach to predicate offenses in other contexts. 

These cases demonstrate that, although the categorical 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 ultimately 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 convictions 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 unusual, 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 statutory sentencing range.

The conviction for the manufacture and/or delivery of 1-15 

grams of cocaine obviously runs into the same Ruth categorical 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 mismatch 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 history qualifying as a valid prior felony drug conviction, however, 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 remaining 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 validity of that stipulation. Recall that these two individuals 

overdosed (in Heilman’s case, twice) on heroin that was purportedly 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 obtained 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 directly 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 addressing 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 overdoses 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 frequently understood to include the impairment of bodily and mental functions. See United States v. Breshers, 684 F.3d 699, 702–03 (7th Cir. 2012) (citing, 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 conspired 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 serious 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 ineffective in one or more respects in advising him to enter into 

the plea agreement, we agree with the district court’s conclusion that he was not prejudiced. A guilty finding on the serious bodily injury enhancement, coupled with his 2000 conviction 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 operated on the assumption that there were three viable pathways 

to a mandatory life term. But serious questions as to Anderson’s criminal history, which was a gateway to all three of 

these paths, were overlooked. Although the categorical mismatch problem with two of Anderson’s prior drug convictions 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 inquire 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 government did not rely on the alternative pathways to a life term in 

the prior appeal when it argued that Anderson was not prejudiced 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 obviously within the knowledge and contemplation of the government 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 judgment.