When you’ve blown a Rule 90 Request for Admissions and want to get out of what you’ve been deemed to admit, you’ve got to clear two (count ’em, two) bars.

Judge Elizabeth A. (“Tex”) Copeland will show you how, as she lets Cindat Manhattan Hotel Portfolio LLC, Docket No. 12905-20-, filed 3/20/24, out of at least some of theirs. Cindat missed three (count ’em, three) Requests, but woke up a couple weeks (hi, Judge Holmes) after the last was deemed, and wanted out. Cindat claimed “additional facts and items of proposed evidence have come about, and therefore Petitioner should not be subject to deemed admitted Admissions that are inconsistent with the evidence.” Order, at p. 1.

Looks like Cindat either changed counsel or retained counsel; good move.

First bar. Show facts that refute the deemed admissions. Merely claiming IRS can’t prove what you are deemed to have admitted isn’t enough. Show what you will prove (and can prove) on the trial. And DKI (deny knowledge or information sufficient to form a belief as to the truth of the deemed) is also a nonstarter. “We may deny a taxpayer’s motion to withdraw deemed admissions when it claims it has insufficient information to admit or deny facts of which it has personal knowledge.” Order, at p. 2. (Citation omitted). In short, you have enough to go to trial.

Second bar. Prejudice to IRS. “We should not lightly weigh the burdens of establishing admissions for a party who properly uses Rule 90 to advance litigation initiated by the opposing party. But neither should we find prejudice merely because the party who obtained the admissions would need to pursue its case on the merits.” Order, at p. 2. (Citations omitted). For example, a witness formerly available is now unavailable, documents formerly existing destroyed (e-mails purged), or last-minute attempts to disrupt trial strategy (ambush). In short, unfair surprise.

Cindat finds fault with IRS’ requests; claims they’re ambiguous. Judge Tex Copeland agrees, and lets Cindat clear up the ambiguities on the trial. Of course, any lawyer who can’t find an ambiguity should find another way to make a living. And IRS knew these objections to admissions were on the table, because Cindat had earlier moved to withdraw the admissions (denied without prejudice).

Admissions calling for legal conclusions going to the matters at the heart of the controversy are of course subject to withdrawal.

But the Request for Admissions remains a useful tool for pinning down an adversary. Draft carefully.