In this diversity action, plaintiffs Mark S. Rose and Frederic G. Rose (the “Roses”) appeal from the December 17, 2003 judgment of the District Court finding the Roses’ 1986 assignment of a life insurance policy subordinate to defendant AmSouth Bank’s (“AmSouth”) 1997 assignment of the same policy. Though the District Court found that plaintiffs had a valid assignment under New York law, the Court concluded that plaintiffs were es-topped from establishing priority over Am-South’s second-in-time assignment because it found that plaintiffs had “totally failed to protect their assignment.”
Rose v. Amsouth Bank of Fl.,
BACKGROUND
The present case arises out of conflicting assignments of a life insurance policy issued by Fidelity Mutual Life Insurance Company (“Fidelity”). The Roses obtained their assignment first, on May 19, 1986, in conjunction with an agreement to make certain premium payments on behalf of the insured pursuant to a “Split Dollar Agreement.”
Rose,
When the insured died on March 21, 1999, counsel for the Roses sent Fidelity a copy of the March 19,1986 assignment and Split Dollar Agreement and demanded payment. Id. at 387-88. On April 5, 1999, Fidelity declined to honor the Roses’ assignment. 1 Id. AmSouth sent Fidelity a claim letter on October 20, 1999, and Fidelity paid AmSouth the entire net proceeds of the policy. Id. at 393. The Roses demanded payment from AmSouth. Am-South refused, and the Roses sued both Fidelity and AmSouth.
Because Fidelity was then undergoing bankruptcy proceedings in Pennsylvania, the District Court dismissed plaintiffs’ complaint against Fidelity, 2 and plaintiffs continued their action solely against defen *65 dant. After a bench trial, the District Court found that plaintiffs were not entitled to recover their assigned portion of the insurance proceeds from AmSouth. Id. at 400. On appeal, plaintiffs argue (1) that defendant did not raise the affirmative defense of estoppel in the pleadings and consequently waived the defense, and (2) that the District Court erred in subordinating plaintiffs’ valid prior assignment to defendant’s subsequent assignment.
DISCUSSION
On appeal from a bench trial, we review the District Court’s factual findings for clear error and its conclusions of law
de novo.
Mixed questions of law and fact are also reviewed
de novo. See, e.g., Oscar Grass & Son, Inc. v. Hollander,
I. Unpleaded Affirmative Defenses
Federal Rule of Civil Procedure 8(c) requires parties to raise affirmative defenses, such as estoppel and laches, in the pleadings.
3
Notwithstanding that requirement, failure to plead an affirmative defense does not necessarily result in waiver. We have recognized that “waiver [of an unpleaded defense] may not be proper where the defense is raised at the first pragmatically possible time and applying it at that time would not unfairly prejudice the opposing party.”
Am. Fed. Group, Ltd. v. Rothenberg,
AmSouth first asserted its estoppel defense at the summary judgment stage of this litigation. At that time, the Roses had an opportunity to respond substantively to the defense. They also had the opportunity to object to AmSouth’s failure to raise estoppel formally in the pleadings. The Roses did not object. Nor do they argue on appeal that they were prejudiced by AmSouth’s procedural error. Consequently, the District Court properly considered the merits of AmSouth’s estoppel defense.
See Curry v. City of Syracuse,
II. The Merits of AmSouth’s Estoppel Defense
Although AmSouth’s estoppel defense was properly considered by the District Court, the Court erred in concluding that AmSouth had presented sufficient evidence of the defense to justify subordinating the Roses’ first-in-time assignment. As an initial matter, the alleged failure of the Roses to provide proper notice to Fidelity of their assignment, even if proven, would not in and of itself have affected the priority of the Roses’ assignment. The relevant New York authorities, including those relied on by the District Court, have explicitly held that notice to the debtor is
not
required to preserve the priority of an
*66
earlier assignment.
See, e.g., Fortunato v. Patten,
The District Court acknowledged this rule and then found that the Roses were estopped from asserting their superi- or title because their failure to give notice to Fidelity misled AmSouth into accepting the subsequent assignment as collateral.
Rose,
The District Court’s additional finding, that Fidelity may never have had notice of the Roses’ assignment,
Rose,
Having failed to establish an affirmative defense that would justify subordinating the Roses’ prior assignment, Am-South holds its assignment subject to the general New York rule, under which, “[a]s between successive assignees of the same chose in action[,] priority in point of time establishes priority of right ... without regard to the date of notification to the debtor.”
Rochester Ropes, Inc. v. Scherl,
CONCLUSION
For the reasons stated above, we conclude that:
(1) defendant did not produce sufficient evidence at trial to support an estoppel defense; and
(2) under New York law, in the circumstances presented, plaintiffs’ valid first-in-time assignment is entitled to priority over defendant’s subsequent assignment.
Accordingly, we reverse the judgment of the District Court and remand the cause with instructions to enter judgment in favor of plaintiffs and award appropriate damages.
Notes
. In its letter denying the Roses' claim, Fidelity stated that it had received information that the Split Dollar Agreement was no longer operative. But it is not clear why Fidelity concluded that the validity of the Roses' assignment hinged on the operativeness of the Agreement. The fact that the Roses had stopped making payments under the Agreement in 1993 should not have affected the Roses’ entitlement to the payments they had already made.
. The Commonwealth Court of Pennsylvania established a separate process for the adjudication of claims against Fidelity, and the District Court found that plaintiffs should pursue their claim against Fidelity in those proceedings.
Rose,
. Federal Rule of Civil Procedure 8(c) provides in relevant part:
In pleading to a preceding pleading, a party shall set forth affirmatively accord and satisfaction, arbitration and award, assumption of risk, contributory negligence, discharge in bankruptcy, duress, estoppel, failure of consideration, fraud, illegality, injury by fellow servant, laches, license, payment, release, res judicata, statute of frauds, statute of limitations, waiver, and any other matter constituting an avoidance or affirmative defense.
. In reaching its conclusion that New York , law subordinated the Roses’ prior assignment, the District Court relied on
Salem Trust Co. v. Manufacturers’ Finance,
