Ray v. Ray, 22 F.4th 69

Post-divorce (1993) Ames invested $500,000 with Christina; Christina agreed to indemnify up to $350,000 for trading losses; Ames lost substantially all funds and sued Christina for breach in 1998 (ongoing).
Christina mortgaged her co-op in 2008 for $500,000 and transferred proceeds to hedge funds; Ames brought fraudulent-conveyance suits in 2010 and 2014; both were dismissed and the dismissals affirmed by the Appellate Division.
Ames filed a 2018 federal fraudulent-conveyance action within six months of the 2014 dismissal affirmance; Judge Daniels held that CPLR §205(a) saved that filing as timely, but dismissed on other grounds; the Second Circuit affirmed that dismissal.
In July 2020 Ames filed another state-court fraudulent-conveyance action (removed to federal court); Christina moved to dismiss as time-barred under the six-year statute of limitations; Ames invoked CPLR §205(a) again as saving the 2020 Action.
The district court (Engelmayer, J.) dismissed the 2020 Action as untimely, holding §205(a) cannot be used to "chain" successive filings where the prior action itself was only timely via §205(a); Ames appealed.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether CPLR §205(a) permits successive refilings when the prior action was itself saved by §205(a)	§205(a) can be applied iteratively; each successor is timely if filed within six months of the prior dismissal	§205(a) requires the new action "would have been timely commenced at the time of commencement of the prior action," so it cannot be chained	§205(a) cannot be chained; the 2020 Action is untimely and dismissal is affirmed
Whether the Court should certify the statutory-interpretation question to the NY Court of Appeals	Certify the question due to alleged uncertainty	Opposed; removal and federal resolution appropriate	Certification declined: statute plain, certification would burden parties and delay resolution

Diffley v. Allied-Signal, Inc., 921 F.2d 421 (2d Cir. 1990) (§205(a) grants a single additional six‑month opportunity after a timely first complaint is dismissed on non‑merits grounds)
U.S. Bank Nat’l Ass’n v. DLJ Mortg. Cap., Inc., 122 N.E.3d 40 (N.Y. 2019) (describes §205(a) as saving a subsequent action within six months of a non‑merits dismissal of a timely initial action)
George v. Mt. Sinai Hosp., 390 N.E.2d 1156 (N.Y. 1979) (explains §205(a)’s function to provide a second opportunity when the initial suit fails for non‑merits reasons)
Hakala v. Deutsche Bank AG, 343 F.3d 111 (2d Cir. 2003) (discusses §205(a)’s purpose to avert unfairness by allowing refiling after curable procedural defects)
Penguin Grp. (USA) Inc. v. Am. Buddha, 609 F.3d 30 (2d Cir. 2010) (explains that certification to a state court is discretionary)
53rd St., LLC v. U.S. Bank Nat'l Ass'n, 8 F.4th 74 (2d Cir. 2021) (notes practical drawbacks of certification: increased expense and delay)