Cementing Admissions: Second Circuit Confirms Rule 36 Requests May Address the “Application of Law to Fact” and Upholds Strict Consequences for Non-Response

1. Introduction

In Cement and Concrete Workers District Council Welfare Fund v. Manny P. Concrete Co., Inc., the United States Court of Appeals for the Second Circuit confronted the perennial dilemma that arises when litigants ignore discovery obligations—specifically, requests for admissions under Federal Rule of Civil Procedure 36. The dispute pitted a group of multi-employer ERISA fringe-benefit funds, their fiduciary, and an affiliated union (collectively “the Funds” or “Plaintiffs”) against two related concrete companies, Manny P. Concrete Co., Inc. and Manny P. Con Industries, Inc. (“Defendants”). The Funds alleged that Defendants failed to make required fringe-benefit contributions and dues check-offs under a collective bargaining agreement (“CBA”).

After protracted discovery skirmishes in the Eastern District of New York—including repeated missed deadlines, partial productions, and an unaddressed set of Rule 36 requests—the district court (Kuntz, J.) granted summary judgment to the Funds. The Second Circuit’s July 21, 2025 opinion affirms that result, crystallising two interconnected principles:

Rule 36 requests may properly seek admissions about facts, the application of law to fact, or opinions about either; and
Failure to respond in a timely manner can and will operate as a binding admission, with district courts enjoying broad discretion to refuse withdrawal—even where the merits or absence of prejudice might otherwise justify leniency.

2. Summary of the Judgment

The Court of Appeals (Livingston, C.J., Jacobs & Menashi, JJ.) issued three core holdings:

Validity of the Requests for Admissions: Plaintiffs’ requests, although touching on whether certain work qualified as “Covered Work” under the CBA, were permissible because they concerned factual matters or, at most, the application of law to fact—squarely within Rule 36(a)(1)(A).
Deemed Admissions & No Withdrawal: Defendants never answered one set of requests and answered the second set months late. The district court did not abuse its discretion in deeming the matters admitted or in refusing to allow withdrawal long after discovery closed. Deemed admissions “conclusively established” the facts for purposes of summary judgment.
Summary Judgment: With the admissions in hand, and given Defendants’ discovery sanctions (precluding late-produced documents), no genuine dispute of material fact existed as to liability or damages. The appellate court therefore affirmed the award of more than $694,000 in delinquent contributions and check-offs.

3. Analysis

3.1 Precedents Cited

Donovan v. Carls Drug Co., 703 F.2d 650 (2d Cir. 1983) – Established that withdrawal of admissions under Rule 36(b) rests in the district court’s discretion.
Moosman v. Joseph P. Blitz, Inc., 358 F.2d 686 (2d Cir. 1966) – Early recognition that unanswered admissions may support summary judgment.
S.E.C. v. Dynasty Fund, Ltd., 121 F. App’x 410 (2d Cir. 2005) – Reiterated appellate deference to district court decisions on Rule 36.
Conlon v. United States, 474 F.3d 616 (9th Cir. 2007) – Persuasive authority on Rule 36(b) discretion, cited to illustrate nationwide coherence.
Syracuse Broad. Corp. v. Newhouse, 271 F.2d 910 (2d Cir. 1959) – Earlier, more restrictive approach to pure legal conclusions, contrasted with the modern rule.
Rule-driven caselaw on summary judgment (Jones v. County of Suffolk, 936 F.3d 108 (2d Cir. 2019); Holtz v. Rockefeller & Co., 258 F.3d 62 (2d Cir. 2001)) further framed the analysis.

Collectively, these authorities paved the way for the panel’s articulation of a fresh, more explicit affirmation that admissions may relate to the application of law to fact, and that deeming them admitted is an integral enforcement mechanism, not a draconian “gotcha.”

3.2 Legal Reasoning

Rule 36 Scope. The Court emphasised the 1970 amendment allowing requests that “apply law to fact.” Thus, asking whether certain employees performed “Covered Work” (a mixed question) was proper.
Operation of Rule 36(a)(3). Because Defendants failed to serve answers within 30 days, the requests were automatically admitted.
Rule 36(b) Withdrawal Standard. Even if withdrawal would (i) promote resolution on the merits and (ii) not prejudice the opposing party, the rule is permissive (“may allow”), leaving discretion to the district court. Here, withholding relief was justified because:
- Discovery had closed nearly two years before the motion;
- Plaintiffs had built their case strategy on the deemed admissions; and
- Defendants had shown a pattern of dilatory conduct untethered to the prior lawyer’s illness.
Impact on Summary Judgment. Once admitted, the facts became “conclusively established.” Defendants’ late-produced, self-serving documents and affidavits could not create a triable issue under Fed. R. Civ. P. 56 because they directly contradicted their own admissions.

3.3 Impact of the Decision

Discovery Discipline. Litigants in the Second Circuit now have explicit appellate warning: ignoring Rule 36 requests is perilous. Courts can and will bind parties to non-responses, even where the admissions effectively decide the case.
Clarification of RFA Scope. Practitioners often debate whether an RFA that blends factual predicates with legal terms (e.g., “Covered Work,” “alter ego,” “employment relationship”) is permissible. The opinion removes doubt—such mixed requests are valid when tethered to the case’s factual matrix.
ERISA Contribution Litigation. Multi-employer funds frequently rely on payroll audits. The decision arms them with a potent procedural tool: targeted RFAs can force employers either to concede the audit or mount a timely, well-supported rebuttal.
Withdrawal Standard Strengthened. By citing Donovan for the proposition that even satisfied Rule 36(b) criteria do not compel relief, the Circuit imbues district courts with firmer discretion—likely leading to fewer successful motions to withdraw.
Settlement Leverage. Because deemed admissions expedite liability findings, plaintiffs may gain stronger bargaining positions, possibly reducing litigation costs and delay.

4. Complex Concepts Simplified

Rule 36 Requests for Admissions (RFA): Written questions served on a party demanding that they admit or deny specific propositions. Silence equals admission after 30 days.
“Application of Law to Fact”: A statement that intertwines a legal term with a factual assertion (e.g., “Employee X performed ‘Covered Work’ as defined by the CBA”). Rule 36 explicitly allows RFAs on such matters.
Section 515 of ERISA (29 U.S.C. § 1145): Requires employers who are signatories to a collective bargaining agreement to make timely contributions to fringe-benefit plans.
Summary Judgment (Rule 56): A mechanism for disposing of a case without trial when no genuine dispute of material fact exists and the movant is entitled to judgment as a matter of law.
CBA “Covered Work”: Labor tasks falling within a union agreement’s jurisdiction. Whether a task is covered determines whether fringe-benefit contributions are owed.
Discovery Sanctions: Court-imposed penalties (e.g., evidentiary preclusion) for failure to comply with discovery obligations.

5. Conclusion

The Second Circuit’s decision in Cement and Concrete Workers District Council Welfare Fund v. Manny firmly “cements” the procedural consequences of failing to answer Rule 36 requests. By validating requests that ask parties to apply law to factual scenarios and by reaffirming broad discretion to deny withdrawal of admissions, the Court reinforces the integrity of pre-trial discovery and underscores that silence is not a defensible litigation strategy.

Practitioners must now treat every RFA with heightened seriousness. A missed deadline can irrevocably concede critical facts, pave the way for summary judgment, and doom a defense—even in high-stakes, document-heavy ERISA contribution actions. The ruling therefore strengthens the procedural backbone of federal litigation and provides clear guidance: respond timely, respond fully, or risk having your position permanently set in stone.