The “Substantial-Interdependence” Rule: Second Circuit Allows Joinder of Fraud and Tax Counts and Declines Per-Se Ineffective-Counsel Claim in United States v. Wynder

1. Introduction

In United States v. Wynder, Jr., Nos. 24-213(L), 24-263(CON) (2d Cir. Aug. 7 2025), the Second Circuit addressed a knot of recurrent trial-management and constitutional questions:

When may the Government try wire-fraud charges alongside tax-evasion charges under Federal Rule of Criminal Procedure 8(b)?
What showing is required before an attorney’s serious illness becomes per se ineffective assistance of counsel?
How much evidence is necessary to sustain a fraud conviction predicated on circumstantial proof of intent?
How should restitution be calculated when misappropriated funds are later spent in ways that arguably benefit the victims?

The defendants—union president Kenneth Wynder, Jr. and outside benefits broker Andrew Brown—were convicted in the Southern District of New York for siphoning \$529,000 from a union-member annuity fund, and (as to Wynder) for concealing related income from the IRS. They appealed on multiple grounds: mis-joinder, evidentiary insufficiency, discovery violations, alleged prosecutorial misconduct, ineffective assistance (because lead counsel developed Creutzfeldt-Jakob Disease), and restitution error. Judge Debra Ann Livingston, writing for a unanimous panel, affirmed across the board.

2. Summary of the Judgment

The Court held:

Proper Joinder. Wire-fraud and tax-evasion counts were properly joined because the indictment alleged “substantial identity of facts and participants.” The same funds siphoned through the fraud enabled the tax crimes, satisfying Rule 8(b). Severance was not required under Rule 14(a) because any spill-over prejudice was cured by limiting instructions.
Sufficient Evidence. Circumstantial evidence—particularly Brown’s falsified withdrawal forms, misleading statements to union members, and personal economic motive—amply proved fraudulent intent.
No Per Se Ineffectiveness. An attorney’s degenerative brain disease, without proof of actual deficient performance, does not qualify for the narrow category of per se Sixth-Amendment violations.
Discovery & Summation. The district court’s sanctions for late discovery (continuance + accelerated Jencks + compliance plan) were sufficient; the prosecutor’s references to “they” and “them” in summation did not constitute plain-error misconduct.
Restitution. Ordering restitution in the full amount withdrawn was not plainly erroneous; any incidental benefits to union members were speculative and did not clearly offset the loss.

3. Analysis

3.1 Precedents Cited and Their Influence

United States v. Rittweger, 524 F.3d 171 (2d Cir. 2008) – articulated the “substantial identity of facts or participants” test for joinder; the Wynder panel applies and slightly sharpens this test.
United States v. Turoff, 853 F.2d 1037 (2d Cir. 1988) and Shellef, 507 F.3d 82 (2d Cir. 2007) – earlier cases limiting joinder when most unreported income stemmed from sources unrelated to the fraud; Wynder distinguishes them, stressing the causal interdependence of the schemes here.
Strickland v. Washington, 466 U.S. 668 (1984) – the baseline two-prong test for ineffective assistance; reaffirmed as the default where per se categories do not apply.
Bellamy v. Cogdell, 974 F.2d 302 (2d Cir. 1992) (en banc) – held that attorney illness is evaluated under Strickland, not as a categorical violation; Wynder follows Bellamy.
Kousisis v. United States, 145 S. Ct. 1382 (2025) – clarified that wire fraud covers schemes aimed at obtaining money “regardless of whether the victim is left worse off”; relied on to dismiss Brown’s insufficiency claim.
Zafiro v. United States, 506 U.S. 534 (1993) – governing standard for severance; cited to emphasize that limiting instructions usually suffice.
Marcus, 560 U.S. 258 (2010) – plain-error framework for unpreserved restitution arguments.

3.2 The Court’s Legal Reasoning

Joinder – the new “Substantial-Interdependence” gloss.
The indictment alleged that (i) Wynder and Brown fraudulently transferred annuity funds into the union operating account, and (ii) Wynder’s tax evasion consisted of failing to report income that would not have existed but for the fraudulent transfers. This overlap created a “substantial interdependence” between the fraud and tax offenses. The Court signals that where the proceeds of one scheme directly enable a subsequent tax offense, joinder is normally proper. The opinion distinguishes earlier precedents by underscoring the causal nexus, not merely temporal overlap.
Severance – prejudice threshold.
Even assuming some jury “spill-over,” the district court’s repeated charge that “guilt is personal and individual” mitigated risk. Prejudice requires a showing “so severe as to amount to a miscarriage of justice.” Brown’s generalized discomfort with being tried alongside Wynder did not meet that bar.
Fraud Intent – circumstantial mosaic.
Brown argued that no witness heard him admit wrongdoing. The panel reminds practitioners that intent can be inferred from: (a) false paperwork, (b) inconsistent explanations to victims, (c) personal pecuniary motive, and (d) continued misconduct after auditor warnings. A single egregious act (here, the \$40k “insurance-premium” withdrawal) can suffice to connect a defendant knowingly to the broader scheme.
Ineffective Assistance – narrow per se categories.
The Court refuses to expand per se ineffectiveness beyond “rare situations” (e.g., attorney implicated in the crime, total absence of counsel, or unlicensed representation). Illness—even fatal, degenerative illness—does not automatically render performance deficient; actual errors must be shown. The panel leaves a traditional Strickland claim to § 2255 proceedings.
Discovery & Summation – discretion and plain error.
Late disclosure, while serious, is remedied by continuances and disclosure orders absent bad faith. Prosecutorial summation is judged in full context; use of collective pronouns is not misconduct where supported by evidence.
Restitution – reasonable approximation.
Because LEEBA commingled funds and record-keeping was opaque, defendants could not show an “obvious” offset benefiting victims. Therefore, ordering restitution equal to the gross withdrawals did not constitute plain error.

3.3 Likely Impact of the Decision

Criminal Joinder Practice. Prosecutors in the Second Circuit now have clearer authority to join fraud and tax counts when the proceeds of one are the subject of the other. Defense counsel should anticipate more multi-count indictments and be prepared to make factual, not merely categorical, objections to joinder.
Ineffective Assistance Litigation. The decision underscores the extremely limited nature of per se ineffectiveness. Defendants alleging counsel illness must marshal concrete examples of deficient performance and prejudice.
Restitution Calculations. Where defendants misappropriate fungible funds and victims cannot trace benefits, courts may award restitution equal to the gross takings. Defendants bear a heavy burden to prove specific value returned.
Audit Obstruction. The opinion signals that delaying or providing partial information to auditors can be persuasive evidence of fraudulent intent. Fiduciaries should treat audit requests with utmost candor.

4. Complex Concepts Simplified

Rule 8(b) Joinder: Allows multiple defendants to be tried together when the charged offenses arise from the “same series of acts.” The Court now stresses “substantial interdependence”—the acts must be factually entangled, not just similar.
Rule 14(a) Severance: Even if joinder is proper, a judge may split trials to prevent actual (not speculative) prejudice that cannot be cured by instructions.
Per Se Ineffective Assistance: Certain extraordinary circumstances (e.g., lawyer has undisclosed conflict, is not licensed, or completely fails to appear) automatically violate the Sixth Amendment without needing to prove prejudice.
Strickland Test: Two-part inquiry: (1) counsel’s performance fell below professional norms; (2) a reasonable probability exists that the outcome would differ but for the errors.
Mandatory Victims Restitution Act (MVRA): Requires courts to order restitution equal to “the full amount of the victim’s loss,” calculated by a “reasonable approximation.” Benefits incidentally flowing back to the victim can reduce the figure, but the defendant bears the burden of tracing them.

5. Conclusion

United States v. Wynder clarifies multiple facets of federal criminal practice:

It adopts a pragmatic “substantial-interdependence” benchmark for joining fraud and tax counts, emphasizing causal and financial links over rigid categorical rules.
It reaffirms that attorney illness alone is insufficient for automatic Sixth-Amendment relief, thereby cabining per se ineffective-counsel doctrine.
It illustrates how circumstantial mosaics—text messages, inconsistent explanations, personal gain, and audit obstruction—can satisfy the demanding standard for proving fraudulent intent.
Finally, it signals that courts will not lightly disturb district-court discretion on discovery sanctions, prosecutorial summations, or restitution approximations absent clear, outcome-determinative error.

Collectively, these holdings strengthen prosecutorial flexibility in complex, multi-facet financial cases while delineating the limits of defendants’ procedural and constitutional challenges. Practitioners should take heed of the Court’s insistence on fact-specific showings and its willingness to apply existing doctrines with renewed clarity.