23-370 Margolies v. United States

UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT

SUMMARY ORDER

RULINGS BY SUMMARY ORDER DO NOT HAVE PRECEDENTIAL EFFECT. CITATION TO A SUMMARY ORDER FILED ON OR AFTER JANUARY 1, 2007, IS PERMITTED AND IS GOVERNED BY FEDERAL RULE OF APPELLATE PROCEDURE 32.1 AND THIS COURT’S LOCAL RULE 32.1.1. WHEN CITING A SUMMARY ORDER IN A DOCUMENT FILED WITH THIS COURT, A PARTY MUST CITE EITHER THE FEDERAL APPENDIX OR AN ELECTRONIC DATABASE (WITH THE NOTATION “SUMMARY ORDER”). A PARTY CITING TO A SUMMARY ORDER MUST SERVE A COPY OF IT ON ANY PARTY NOT REPRESENTED BY COUNSEL.

At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 16th day of October, two thousand twenty-four.

PRESENT:

PIERRE N. LEVAL, RICHARD J. SULLIVAN, SARAH A. L. MERRIAM, Circuit Judges. _____________________________________

WOLFE MARGOLIES,

Petitioner-Appellant,

v. No. 23-370

UNITED STATES OF AMERICA,

Respondent-Appellee. _____________________________________ For Petitioner-Appellant: BENJAMIN D. WHITE, Bloch & White LLP, New York, NY.

For Respondent-Appellee: ADAM SOWLATI (Nathan Rehn, on the brief), Assistant United States Attorneys, for Damian Williams, United States Attorney for the Southern District of New York, New York, NY.

Appeal from a judgment of the United States District Court for the Southern

District of New York (Kimba M. Wood, Judge).

UPON DUE CONSIDERATION, IT IS HEREBY ORDERED,

ADJUDGED, AND DECREED that the January 17, 2023 order of the district court

is VACATED and REMANDED.

Wolfe Margolies appeals from the district court’s order denying his motion

to vacate his conviction under

, asserting that he received

ineffective assistance of counsel with respect to his plea of guilty to a two-count

indictment. We assume the parties’ familiarity with the underlying facts,

procedural history, and issues in dispute, to which we refer only as necessary to

resolve this appeal.

In February 2019, Margolies was charged by criminal complaint with one

count of conspiracy to distribute heroin, in violation of 21 U.S.C. §§ 84l(b)(l)(C)

2 and 846 (“Count One”), and one count of possession of child pornography, in

violation of 18 U.S.C. § 2252A(a)(5)(B), (b)(2) (“Count Two”). Although the

complaint linked one of Margolies’s heroin sales to the death of an individual in

February 2018, it did not charge him under the enhanced sentencing provision for

that offense, which carries a mandatory minimum term of twenty years’

imprisonment for distribution where “death . . . results from the use of such

substance” (a “Death-Results Charge”).

(b)(1)(C). On March 13,

2019, a grand jury returned an indictment charging Margolies with the same two

counts contained in the complaint. Margolies later pleaded guilty to both counts

pursuant to a plea agreement. As part of that agreement, he stipulated to a base

offense level of 38 for Count One, because “the offense of conviction establishe[d]

that death . . . resulted from the use of the substance” he distributed, App’x at 56

(citing U.S.S.G. § 2D1.1(a)(2)), and a total Sentencing Guidelines range of 168 to

210 months’ imprisonment. The district court ultimately sentenced Margolies

principally to 168 months’ imprisonment on each count, to run concurrently.

Although Margolies appealed his sentence, we dismissed the appeal as

barred by the waiver of appellate rights contained in his plea agreement. He

subsequently filed a pro se motion seeking to vacate his sentence under section

3 2255, asserting that his trial counsel rendered ineffective assistance with respect to

his decision to plead guilty. As to Count One, Margolies contended that his

counsel failed to advise him about the proper causation standard that the

government needed to meet to prove that a death resulted from his heroin sale,

and relatedly, that counsel failed to adequately investigate the factual basis for any

death-resulting application. 1 As to Count Two, he asserted that counsel failed to

inform him of an affirmative defense – for which he contends he was eligible –

available to defendants who possessed fewer than three images of child

pornography and “promptly and in good faith . . . took reasonable steps to destroy

each such image.” 18 U.S.C. § 2252A(d). Margolies represented that, but for

counsel’s deficient performance, he would have either maintained his not-guilty

plea and proceeded to trial, or at the very least pleaded guilty to the indictment

without a plea agreement so he could contest the base offense level for Count One

1 To prevail on the statutory Death-Results Charge under section 841, the government must prove that (1) the defendant knowingly or intentionally distributed a controlled substance and (2) that controlled substance was the but-for cause of the decedent’s death. See Burrage v. United States,

, 217–19 (2014). Under this causation requirement, the decedent’s death must “‘result from’ use of the unlawfully distributed drug, not from a combination of factors to which drug use merely contributed.”

; see also

, 218–19 (reversing a conviction where the government could not prove beyond a reasonable doubt that the decedent “would have lived had he not taken the heroin” the defendant sold him). The parties do not dispute that the same but-for causation requirement is applicable to the Guidelines offense level under section 2D1.1(a)(2). 4 under U.S.S.G. § 2D1.1(a)(2). The district court denied Margolies’s motion

without an evidentiary hearing, concluding in principal part that he had failed to

demonstrate any deficient performance by counsel.

In the section 2255 context, we review factual findings for clear error and

questions of law de novo. See Thomas v. United States,

(2d Cir. 2024).

The question of whether counsel provided ineffective assistance is a mixed

question of law and fact that we review de novo. See Puglisi v. United States,

(2d Cir. 2009). A defendant alleging ineffective assistance of counsel

must show that the counsel’s performance (1) “fell below an objective standard of

reasonableness” under “prevailing professional norms,” and (2) was “prejudicial”

to his defense, meaning there exists “a reasonable probability that, but for

counsel’s unprofessional errors, the result of the proceeding would have been

different.” Strickland v. Washington,

(1984).

When a district court declines to hold an evidentiary hearing on a section

2255 motion, we review that decision for abuse of discretion. See Gonzalez v.

United States,

(2d Cir. 2013). Under section 2255, the district

court “shall . . . grant a prompt hearing” “[u]nless the motion and the files and

records of the case conclusively show that the prisoner is entitled to no relief.” 28

(b). Thus, to obtain a hearing, a claimant “need establish only that

he has a plausible claim of ineffective assistance of counsel, not that he will

necessarily succeed on the claim.” Raysor v. United States,

(2d

Cir. 2011) (internal quotation marks omitted). While we have recognized that a

“district court may use methods under [s]ection 2255 to expand the record without

conducting a full-blown testimonial hearing,” Chang v. United States,

(2d Cir. 2001), a remand for further factual development is appropriate when

the district court summarily dismisses a habeas petition in the absence of a

sufficient record, see Pham v. United States,

(2d Cir. 2003).

The record before the district court did not support summary denial.

“[E]xcept in highly unusual circumstances,” a district court facing an ineffective

assistance claim should “offer the assertedly ineffective attorney an opportunity

to be heard and to present evidence, in the form of live testimony, affidavits, or

briefs” that address the assertions of deficient performance. Sparman v. Edwards,

(2d Cir. 1998). This is especially true when a defendant’s claims

“implicate actions taken by counsel outside the presence of the trial judge,”

Armienti v. United States,

(2d Cir. 2000), and “therefore cannot be

6 determined by examining the motion, files, and records before the district court,”

Chang,

.

Here, the district court never solicited an affidavit or testimony from trial

counsel, but instead denied Margolies’s motion based on his statements at his

guilty plea hearing and information contained in his presentence investigation

report (“PSR”). Specifically, as to Count One, the district court concluded that

Margolies’s plea-hearing statements made clear that he knowingly and

intelligently understood the nature and consequences of his plea agreement and

allocuted to the death-resulting conduct. But as we have recognized, “counsel’s

deficient performance” – which, according to Margolies, included his counsel’s

failure to inform him of the legal basis for, and to investigate the factual basis of,

the death-resulting offense level – could “undermine[] the voluntary and

intelligent nature of [the] defendant’s decision to plead guilty.” United States v.

Arteca,

(2d Cir. 2005); see also Missouri v. Frye,

(2012) (noting that the Supreme Court has “rejected the argument . . . that a

knowing and voluntary plea supersedes errors by defense counsel”). That

Margolies swore under oath that he understood the consequences of pleading

7 guilty does not squarely foreclose his contentions now that he lacked the legal and

factual information pertinent to assessing that plea. 2

As to Count Two, the district court concluded that counsel’s performance

was not deficient because Margolies had no viable defense under section 2252A(d),

given that the PSR indicated Margolies possessed more than three images of child

pornography on his personal devices and there was “no evidence” that Margolies

took reasonable steps to destroy those images. Sp. App’x at 9–10. But in fact,

the PSR noted that Margolies possessed multiple images of “child erotica,” e.g.,

Sealed App’x at 46, 67 (emphasis added), which is not the same as child

pornography and is not in fact illegal, see United States v. Boles,

(2d

Cir. 2019), and the record does not indicate that Margolies possessed any child

pornography other than the single video forming the basis of his guilty plea. 3

2 We disagree with the government’s contention on appeal that Margolies did not adequately raise this argument in the district court. While Margolies did not explicitly identify but-for causation in his section 2255 motion, his pro se filings – including his supplemental motion for an expert toxicologist, which cites Burrage and does discuss but-for causation, see App’x at 126 – sufficiently raised the argument that counsel failed to adequately investigate and never informed him of the proper causation standard. The district court also recognized that Margolies’s section 2255 motion as to Count One implicated these issues, even though it ultimately rejected them on the grounds that his plea was knowing and voluntary. See Sp. App’x at 4.

3 Although the Sentencing Guidelines commentary explains that a “video” constitutes “75 images” for purposes of sentencing enhancements for child pornography offenses, U.S.S.G. § 2G2.2(b)(7)(a), cmt. n.6(B)(ii), the government does not argue that the same definition applies

8 Moreover, contrary to the district court’s finding, the record does contain some

evidence that Margolies deleted the video after he received and viewed it. 4

Absent further factfinding in the district court, the record relevant to an

assessment of Strickland’s first prong – counsel’s deficient performance – is not

sufficiently developed on either count. Margolies attests that his counsel did not

inform him of the death-resulting causation standard and failed to obtain any

scientific or eyewitness evidence necessary to investigate the circumstances of the

decedent’s death. And save for these contentions, the record is largely devoid of

information regarding whether, leading up to Margolies’s guilty plea, his counsel

made “reasonable investigations” or “ma[de] a reasonable decision that ma[de]

particular investigations unnecessary.” Strickland,

. The parties

vigorously dispute, moreover, whether certain statements made by defense

to section 2252A(d), which is silent on the subject.

4 Margolies consistently maintained during the criminal proceedings that he deleted the video after viewing it. See, e.g., App’x at 79 (Margolies’s plea colloquy indicating that “[he] subsequently deleted the video”); Sealed App’x at 23 (Margolies’s sentencing submission noting that “[a]fter examining the video, [Margolies’s] deleted it”); id. at 55 (PSR detailing Margolies’s account of receiving the video, which indicated that “he was not expecting to see such a video when he clicked on the link” sent to him and “reportedly deleted the video”). And the government represented that the video, which was sent to Margolies on October 25, 2018, was found among materials on his phone that had been deleted as early as October 2018. See App’x at 20, 262–63.

9 counsel during the criminal proceedings indicate that he correctly understood

(and adequately informed Margolies of) the death-resulting causation standard,

and whether the available facts indicate that Margolies had a plausible affirmative

defense on Count Two that his counsel should have considered. Nor can we say,

as the government asserts, that the death-resulting evidence against Margolies at

the time was so “overwhelming” that any failure to investigate further would have

been “objectively reasonable” under the circumstances. United States v. Patasnik,

(2d Cir. 1996). 5

The district court also did not analyze Strickland’s second prong – likely

prejudice – in any great detail. In the plea context, a defendant must typically

demonstrate a “reasonable probability that, but for counsel’s errors, he would not

have pleaded guilty and would have insisted on going to trial.” Hill v. Lockhart,

(1985). Similarly, in the sentencing context, “the defendant must

5 In support of this argument, the government points to the following evidence: text messages indicating that Margolies sold heroin to the decedent and suggesting, in the government’s view, that the decedent did not have an existing heroin supply; the decedent’s last outgoing text message, which was to Margolies; the fact that the decedent was found deceased the following day; and a death certificate – signed by a medical examiner who did not examine the decedent’s body – indicating that the cause of death was acute heroin intoxication. See Gov’t Br. at 25–26; see also App’x at 129. But as Margolies points out, the government had represented at his bail hearing that, as “confirmed by [a] toxicology report,” the decedent had “various heroin” and fentanyl in his system at the time of his death. App’x at 260–61. And the cases cited by the government generally involved more evidence of but-for causation than that identified by the government here. 10 show a reasonable probability that, but for counsel’s substandard performance, he

would have received a less severe sentence.” Gonzalez,

. Here,

Margolies attests that, had he received adequate representation from counsel, he

would have either: (1) pleaded to the indictment without a plea agreement, in

which case he would at least have had the benefit of a Fatico hearing to contest any

death-resulting base offense level or variance on Count One; or (2) proceeded to

trial, holding the government to its burden of proof on a possible Death-Results

Charge on Count One and asserting an affirmative defense on Count Two.

On this record, we decline to resolve the prejudice prong, which entails a

“case-by-case examination of the totality of the evidence” and “focuses on a

defendant’s decisionmaking.” Jae Lee v. United States,

(2017)

(internal quotation marks omitted). As a general matter, where counsel’s alleged

errors are primarily the failure to adequately investigate and the “failure to advise

the defendant of a potential affirmative defense,” the prejudice inquiry turns in

large part on whether the evidence that counsel should have investigated and the

affirmative defense “would have changed the outcome of a trial.” Hill,

. In this case, that inquiry involves some assessment of whether Margolies

could have successfully challenged the death-resulting offense level to Count One

11 at sentencing had he pleaded guilty without any agreement, and whether any

investigatory efforts undertaken by his counsel would have yielded meaningful

exculpatory evidence had the government superseded the indictment and

Margolies proceeded to trial on a potential Death-Results Charge under

section 841(b)(1)(C). It also requires the district court to evaluate anew whether

Margolies could have succeeded in asserting an affirmative defense at trial on

Count Two. 6

The potential sentencing outcomes that Margolies would have faced had he

rejected the government’s plea offer are also relevant to this inquiry. On the one

hand, for example, Margolies would have faced a substantially lower Guidelines

range on Count One if he had been permitted to plead guilty without an agreement

and the government could not prove by a preponderance of the evidence that the

heroin supplied by Margolies was the but-for cause of the decedent’s death. The

same would have been true if the government had superseded the indictment to

add a Death-Results Charge under section 841(b)(1)(C) but failed to prove but-for

6This, in turn, may require the district court to analyze the meaning of the terms “images,” “promptly,” “in good faith,” and “reasonable steps” as they appear in 18 U.S.C. § 2252A(d), all of which may bear on the district court’s assessment not only of likely prejudice, but also of counsel’s performance. 12 causation beyond a reasonable doubt at trial or by a preponderance of the evidence

at sentencing (assuming a conviction on the conspiracy count). And had

Margolies proceeded to trial and succeeded on his affirmative defense to Count

Two, he would have avoided the serious consequences that flow from a conviction

for a child pornography offense.

On the other hand, Margolies obtained obvious sentencing benefits as a

result of his plea agreement. For starters, the plea agreement significantly limited

his criminal and sentencing exposure. See United States v. Morgan,

(2d Cir. 2005). By pleading guilty to Count One, Margolies faced a maximum

term of twenty years’ imprisonment on that count – as opposed to a twenty-year

mandatory minimum sentence and potential life sentence had he been charged with

and convicted on a Death-Results Charge. See 21 U.S.C. § 84l(b)(l)(C). The plea

agreement also precluded the government from prosecuting him in the future for

any conduct relating to his heroin distribution conspiracy (from December 2017

through January 2019) or child pornography possession (from October 2018

through January 2019). And if Margolies insisted on going to trial, he risked

losing the opportunity for a reduction for acceptance of responsibility under the

Sentencing Guidelines. See U.S.S.G. § 3E1.1; Arteca,

. But see

13 U.S.S.G. § 3E1.1 cmt. n.2 (“In rare situations[,] a defendant may clearly

demonstrate an acceptance of responsibility for his criminal conduct even though

he exercises his constitutional right to a trial.”).

In short, the sentencing ramifications of a rejection of the plea agreement are

complicated. As a result, we are convinced that these and other considerations

regarding whether counsel’s purported errors prejudiced Margolies are best

resolved by the district court in the first instance, with the benefit of additional

factfinding as necessary.

* * *

Ultimately, we conclude that Margolies has done enough to state a plausible

claim for relief based on his assertions of ineffective assistance of counsel and that

“[t]he record as it presently exists” – with respect to both his counsel’s purportedly

deficient performance and any prejudice that Margolies suffered as a result –

“does not support denial of” his motion. Pham,

. We therefore

remand for the district court to reevaluate Margolies’s claims after further

developing the relevant record. Of course, in remanding, we note that “a court

deciding an ineffective assistance claim” need not “address both components of

14 the inquiry if the defendant makes an insufficient showing on one.” Strickland,

. We express no opinion on the merits of Margolies’s claims. 7

For the foregoing reasons, the district court’s order is VACATED, and the

case is REMANDED for further proceedings consistent with this order.

FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court

7 We reject Margolies’s request for the “extraordinary remedy” of reassignment to a new judge on remand. United States v. Jacobs,

(2d Cir. 1992) (internal quotation marks omitted). Even if the district judge may have “held erroneous views or made incorrect findings,” Margolies has not demonstrated that the judge’s fairness, or the appearance of that fairness, “is seriously in doubt.” United States v. Bradley,

, 782 n.9 (2d Cir. 1987).

15