New York Claim Preclusion Reaffirmed: “Convenient Trial Unit” Is Non‑Dispositive; Different Contracts Do Not Avoid Res Judicata When Tied to the Same Transactional Nucleus

Introduction

This commentary examines the Second Circuit’s September 10, 2025 summary order in Hay v. Bolonik (No. 24‑2413), affirming dismissal of a second lawsuit brought by Bruce Hay, a law professor proceeding pro se, against journalist Kera Bolonik. The case arises from the aftermath of a high‑profile series of 2019 New York Magazine articles about Hay’s relationship with Maria‑Pia and Mischa Shuman. After Hay’s first action—challenging the reporting and alleging breaches of professional promises—was dismissed and that dismissal was affirmed on appeal in 2022, he filed a second suit in 2023 alleging breaches of alleged oral agreements to co‑author a book and pursue television and movie deals.

The key issue on appeal was whether New York’s claim preclusion (res judicata) doctrine barred the second suit because it arose from the same “transaction or series of connected transactions” as the first action. Hay argued the cases centered on different contracts (articles vs. book/TV), and thus would not have formed a “convenient trial unit.” The Second Circuit rejected that argument and affirmed dismissal on res judicata grounds.

Although issued as a summary order (and therefore non‑precedential under the Second Circuit’s rules), the decision offers a crisp, practical application of New York’s transactional approach to claim preclusion, clarifies the limited role of the “convenient trial unit” factor, and underscores that attorneys appearing pro se receive no special solicitude.

Summary of the Opinion

The Court reviews de novo the district court’s application of res judicata.
Because Hay is an attorney and law professor, he is not entitled to the “special solicitude” typically afforded pro se litigants.
Applying New York claim preclusion law (in this diversity case), the Court holds that the second suit is barred because it arises from the same series of connected transactions as the first suit and could have been brought at that time.
The factual predicates for the book/TV claims were largely available in 2019; Hay filed his first suit in August 2020—thus he could have included those claims then.
Hay’s reliance on Chen v. Fischer (the “convenient trial unit” case from the New York Court of Appeals) is misplaced; “convenient trial unit” is only one factor, and the distinctive policy reasons that controlled Chen (divorce vs. tort claims) do not apply here.
Because the parties, relief, proof, trial format, and fee structures aligned across Hay’s two suits, and the facts significantly overlapped, res judicata bars the second action.
The judgment of dismissal is affirmed.

Analysis

Precedents Cited and Their Influence

TechnoMarine SA v. Giftports, Inc., 758 F.3d 493 (2d Cir. 2014): Cited for the standard of review—application of res judicata is reviewed de novo. This frames the panel’s independent assessment of the district court’s ruling.
Tracy v. Freshwater, 623 F.3d 90 (2d Cir. 2010): Establishes that lawyers representing themselves ordinarily receive no special solicitude. The panel applies this to Hay, an experienced litigator and law professor, signaling rigorous adherence to procedural rules.
Duane Reade, Inc. v. St. Paul Fire & Marine Ins. Co., 600 F.3d 190 (2d Cir. 2010): Reaffirms New York’s transactional approach to claim preclusion, adopting Restatement (Second) of Judgments § 24(1): once a valid, final judgment is entered, the claim extinguished includes all rights to remedies with respect to all or any part of the transaction or series of connected transactions out of which the action arose. This is the backbone of the Court’s preclusion analysis.
Beijing Neu Cloud Oriental Sys. Tech. Co. v. IBM Corp., 110 F.4th 106 (2d Cir. 2024) (quoting In re Hunter, 4 N.Y.3d 260 (2005)): Restates New York preclusion principles: a party may not litigate a claim where a prior judgment on the merits exists between the same parties involving the same subject matter, including claims that “could have been raised” previously.
People v. Applied Card Sys., Inc., 11 N.Y.3d 105 (2008): Provides the two elements under New York law: (i) a judgment on the merits by a court of competent jurisdiction, and (ii) identity of parties (or privity). The prior dismissal for failure to state a claim—affirmed on appeal—satisfies the “on the merits” requirement in this context.
Simmons v. Trans Express Inc., 16 F.4th 357 (2d Cir. 2021): Sets out pragmatic factors for determining whether claims arise from the same transaction or series: relatedness in time, space, origin, or motivation; whether they form a convenient trial unit; and whether their treatment as a unit aligns with the parties’ expectations or business understanding.
Xiao Yang Chen v. Fischer, 6 N.Y.3d 94 (2005) (“Chen v. Fischer”): The leading New York case limiting claim preclusion where tort claims stemming from spousal abuse were not a “convenient trial unit” with a divorce proceeding, emphasizing different relief, proof, trial types (jury vs. bench), fee structures, and public policy. The panel distinguishes Chen on all these grounds in this case.
EFCO Corp. v. U.W. Marx, Inc., 124 F.3d 394 (2d Cir. 1997): Confirms that claims arising out of the same facts are barred even if advanced under different legal theories or seeking different relief. This undercuts Hay’s attempt to evade preclusion by recasting theories and contracts.

Legal Reasoning

The Court applies New York’s transactional approach to claim preclusion. Under that approach, a prior final judgment on the merits bars any subsequent claims between the same parties that were, or could have been, raised and that arise from the same transaction or series of connected transactions.

The panel proceeds in three steps:

Prior final judgment on the merits and identity of parties: Hay’s first action against Bolonik was dismissed for failure to state a claim, and that dismissal was affirmed on appeal in 2022. Under New York law, this operates as a final judgment on the merits for preclusion purposes. The parties are identical—Hay versus Bolonik—satisfying the Applied Card Systems elements.
Same transaction or series of connected transactions: The factual nucleus for both actions substantially overlaps and is concentrated in 2019:
- Early 2019: the parties allegedly agreed on the terms of a co‑authoring and media‑development arrangement.
- August–September 2019: Bolonik allegedly drafted and circulated a book proposal and sold the book.
- Summer 2019: the alleged breach of the co‑authoring/media agreement occurred.
- October 2019: Bolonik allegedly informed Hay that the Shumans’ lawyer was seeking to halt publication.
Hay filed his first action in August 2020, after all of these events. Thus, the later claims could have been asserted in the first suit. The fact that the second complaint invokes different alleged “contracts” (professionalism for articles versus book/TV deals) does not break the transactional link. Per EFCO and Duane Reade, the preclusion inquiry turns on the underlying facts and transactions, not the labels attached to legal theories or instruments.
“Convenient trial unit” is a factor, not dispositive—and Chen is distinguishable: Hay argued that, because the two suits involved different contracts, they would not have formed a “convenient trial unit.” The Court emphasizes that “convenient trial unit” is only one factor in a pragmatic test (Simmons). In Chen, the New York Court of Appeals declined to force joinder of a personal‑injury tort claim into a divorce action based on distinctive differences (relief sought, proof required, trial type, fee structures) and strong policy concerns (avoiding prolonging divorce proceedings and delaying child‑related determinations). None of those rationales apply here. Here, the two suits share significantly overlapping facts; the relief, proof, trial posture, and fee structures align; and combining the matters would neither offend policy nor surprise the parties’ reasonable expectations. Consequently, Chen’s narrow carve‑out offers no refuge.

Impact and Implications

While non‑precedential, the order reinforces several practical points likely to influence litigation strategy in New York federal and state courts:

Broad transactional approach: New York’s res judicata doctrine remains robust. If multiple claims arise from a common factual enterprise—even if they invoke different contracts, media formats (articles, books, TV), or legal theories—they must be brought together or risk being barred.
“Convenient trial unit” is not a silver bullet: Litigants cannot rely on the “convenient trial unit” factor to justify claim‑splitting absent the kind of categorical differences and policy concerns recognized in Chen (e.g., divorce vs. tort).
Attorneys proceeding pro se receive no special solicitude: Courts will strictly hold lawyer‑litigants to procedural obligations, including comprehensive claim joinder.
Timing matters: Facts known by the time of the first suit must be included. Claims based on 2019 conduct could not be reserved for a 2023 second action after a 2020 first filing and a 2022 affirmance.
Different instruments, same nucleus: Even if distinct oral or written agreements can be identified (e.g., professionalism in reporting versus co‑authoring/media deals), res judicata focuses on the factual nexus and business context, not the count labels.
Diversity cases apply state preclusion rules: Federal courts sitting in diversity will apply New York claim preclusion law, including its Restatement‑based transactional test.

Complex Concepts Simplified

Res judicata (claim preclusion): A rule that prevents a party from suing again on the same claim after a final judgment. In New York, it extinguishes all claims that were or could have been brought arising from the same transaction or series of connected transactions.
“Same transaction or series of connected transactions”: A pragmatic, fact‑based test. Courts look at whether the claims are related in time, place, origin, or motivation; whether trying them together would be sensible; and whether combining them fits the parties’ business expectations.
“Convenient trial unit”: One factor in deciding whether claims are part of the same transaction. It can weigh against preclusion when combining claims would be impractical or contrary to policy (as in Chen’s divorce‑versus‑tort context), but it is not dispositive standing alone.
Judgment “on the merits”: A decision that resolves the substance of a claim such that it can bar relitigation. Under New York law, a dismissal for failure to state a claim, when final, typically qualifies for preclusion purposes.
Issue preclusion (collateral estoppel) vs. claim preclusion: Issue preclusion prevents relitigation of specific issues actually decided in a prior case; claim preclusion bars entire claims that were or could have been raised. This case concerns claim preclusion.
Privity: When a non‑party’s interests are so closely aligned with a party’s that preclusion can apply. Here, the panel did not need to reach privity because the same parties litigated both actions.
Special solicitude for pro se litigants: Courts often liberally construe filings from non‑lawyer pro se litigants. But lawyers representing themselves ordinarily receive no such leniency.
Summary order: A non‑precedential appellate disposition in the Second Circuit. It may be cited under FRAP 32.1 and Local Rule 32.1.1, but it does not carry precedential force.

Practice‑Focused Takeaways

Early claim scoping is essential: At the outset, identify all agreements, media formats, and legal theories arising from a common factual narrative. Assume that a later effort to “peel off” related claims for a second suit will be barred.
Do not rely on different contracts to avoid preclusion: If the agreements are part of a single business relationship or media project sequence, separate contract labels will not defeat the transactional test.
Chen v. Fischer has narrow reach: Its exception is anchored in the unique structure and policy of matrimonial and tort litigation. Outside similar categorical divergences, expect courts to enforce joinder under New York’s transactional approach.
Document chronology carefully: When the operative facts predate the first suit (as they did here in 2019), the argument that the claims were unavailable is likely to fail.
Pro se attorneys must meet professional standards: Courts will insist that lawyer‑litigants adhere to the same strategic and procedural rigor expected of represented parties.

Conclusion

The Second Circuit’s summary order in Hay v. Bolonik reinforces New York’s robust, transactional approach to claim preclusion. The Court held that a second lawsuit alleging breaches of separate, later‑invoked contracts (co‑authoring and media deals) was barred because it arose from the same factual nucleus as the first suit concerning the journalist’s 2019 articles and related dealings. The panel clarified that “convenient trial unit” is only one factor in the preclusion analysis and does not override substantial factual overlap, aligned relief and proof, and consistent trial and fee structures. Chen v. Fischer’s exception remains limited to contexts with categorical differences and policy imperatives not present here.

The decision provides a practical warning to litigants: when multiple theories or agreements stem from a single relationship and sequence of events, they must be brought together. For attorneys proceeding pro se, the Court’s reminder is equally clear—no special solicitude will soften the strictures of claim preclusion. Even as a non‑precedential order, the reasoning is a persuasive and timely restatement of New York’s claim‑splitting prohibition and the limited role of “convenient trial unit” in that analysis.