Great Lakes Insurance SE v. Bryan Crabtree

Court of Appeals for the Eleventh Circuit·Decided May 19, 2026·No. 23-12020·Published

Opinion

FOR PUBLICATION

In the

United States Court of Appeals For the Eleventh Circuit

No. 23-12020

GREAT LAKES INSURANCE SE,

Plaintiff-Counter Defendant-Appellant, versus BRYAN CRABTREE, BETHEA CRABTREE,

Defendants-Counter Claimants-Appellees,

M&T BANK,

Defendant.

2 Opinion of the Court 23-12020

Appeal from the United States District Court for the Southern District of Florida D.C. Docket No. 9:20-cv-81544-RKA

Before NEWSOM, LAGOA, and KIDD, Circuit Judges. NEWSOM, Circuit Judge:

Seeking to avoid liability on an insurance policy for a boat fire, Great Lakes Insurance filed a declaratory-judgment action against Bryan and Bethea Crabtree in the United States District Court for the District of Montana. The ensuing litigation has followed a long and winding road, but for present purposes a few events are particularly important. Most importantly, Great Lakes twice voluntarily dismissed its complaints: first in the District of Montana, and then again in a follow-on suit brought in the United States District Court for the Southern District of Florida. It then filed a third case, back in the District of Montana, which was subsequently transferred back to the Southern District of Florida. Not long thereafter, that court granted summary judgment to the Crabtrees under Federal Rule of Civil Procedure 41(a)(1)(B), which states that a second voluntary dismissal constitutes an “adjudication on the merits.” Because we conclude that the second dismissal operated as a dismissal with prejudice, we AFFIRM.

23-12020 Opinion of the Court 3

I

A

The Crabtrees purchased an insurance policy from Great Lakes to cover their boat. The boat suffered extensive fire damage while stored at a service facility in Riviera Beach, Florida. The Crabtrees demanded payment under the policy. Great Lakes denied coverage, maintaining that the Crabtrees hadn’t complied with the policy’s conditions.

B

Great Lakes sued the Crabtrees in the District of Montana, seeking a declaratory judgment that the policy didn’t cover their claim. Why Montana? Because the Crabtrees had listed a Montana address on their insurance application, and the policy’s forum-selection clause provided that policy disputes would be subject to the jurisdiction of the policyholder’s listed address.

For reasons of their own, the parties agreed that Great Lakes would voluntarily dismiss the Montana suit and refile in the Southern District of Florida—hereinafter, to avoid ongoing clunkiness, “SDFL”—with the understanding that the Crabtrees wouldn’t contest service, venue, or personal jurisdiction there. Great Lakes also wanted the Crabtrees to answer the new, SDFL suit once it was filed, but to that request, the Crabtrees didn’t agree. Even so, Great Lakes filed a notice of voluntary dismissal without prejudice in the District of Montana.

4 Opinion of the Court 23-12020

The next day, Great Lakes filed the new declaratory-judgment action against the Crabtrees in SDFL. The Crabtrees responded by counter-suing Great Lakes in Florida state court and moving to stay or dismiss the SDFL lawsuit pending resolution of their state-court action. Great Lakes asserts that in so doing the Crabtrees “breached both the agreement between the parties and the . . . forum selection clause.” Br. of Appellant at 18. Importantly , though, rather than respond to the Crabtrees’ motion, Great Lakes voluntarily dismissed its SDFL lawsuit.

The same day it dismissed the SDFL action, Great Lakes filed this suit—its third—back in the District of Montana. The Crabtrees promptly moved to dismiss. In their reply brief in support of that motion, the Crabtrees argued for the first time that Great Lakes’s suit violated Federal Rule of Civil Procedure 41(a)(1)(B), which, in relevant part, provides as follows: “[I]f the plaintiff [has] previously dismissed any federal- or state-court action based on or including the same claim, a notice of dismissal operates as an adjudication on the merits.” Fed. R. Civ. P. 41(a)(1)(B). Great Lakes’s third action, the Crabtrees argued, was “barred by the preclusive effect of [the] adjudication on the merits” resulting from the second, SDFL dismissal. The district court allowed Great Lakes to file a supplemental brief responding to the Crabtrees’ two-dismissal theory. Great Lakes asserted that because the first, Montana dismissal was pursuant to an agreement between the parties, counting it wouldn’t serve the purpose of Rule 41(a)(1)(B)’s two-dismissal rule. Therefore, their argument went, the rule shouldn’t apply.

23-12020 Opinion of the Court 5

Looking to Rule 41(a)(1)(B)’s “purpose” and citing courts that had done the same—including, most notably, the Second Circuit in Poloron Products, Inc. v. Lybrand Ross Bros. & Montgomery, 534 F.2d 1012 (2d Cir. 1976)—the Montana court denied the Crabtrees’ motion to dismiss “[b]ecause it appear[ed] that the prior dismissals [we]re attributable to gamesmanship on the[ir] part.” Order Den. Mot. to Dismiss at 3–4, Dkt. No. 20. The court reasoned that applying the Rule’s plain text wouldn’t make sense “[b]ecause Great Lakes reasonably relied on the representations made by the Crabtrees ’ counsel” when dismissing the first case; accordingly, the court held, the first dismissal didn’t qualify for Rule 41(a)(1)(B) purposes . Id. at 4.

The case then took an even stranger turn. After the Crabtrees answered Great Lakes’s complaint in the Montana action and Great Lakes successfully moved to dismiss the Crabtrees’ Florida state-court lawsuit, the Crabtrees filed a consented-to motion to transfer Great Lakes’s Montana suit back to SDFL. At that point, all that remained was the one federal action—in SDFL.

When the case landed back in SDFL, the district court ordered summary-judgment briefing on the Rule 41(a)(1)(B) issue. As the court explained, it was undisputed (1) “that Great Lakes voluntarily dismissed two identical actions,” (2) “that the parties agreed to the first voluntary dismissal,” and (3) “that [Great Lakes] unilaterally took the second dismissal.” Order Directing Summ. J. Briefing at 2, Dkt. No. 193. This, the court said, left it “with a pure question of law: Did Great Lakes violate Rule 41 by bringing the

USCA11 Case: 23-12020 Document: 66-1 Date Filed: 05/19/2026 Page: 6 of 12

6 Opinion of the Court 23-12020

same claims after having taken two voluntary dismissals—the first of which was with the [Crabtrees’] consent?” Id. at 3.

The district court granted summary judgment to the Crabtrees , ruling that the “two-dismissal rule means precisely what it says.” Summ. J. Order at 2, Dkt. No. 208 (citation modified). Based on Rule 41(a)(1)(B)’s plain text, the court concluded that the two- dismissal rule applies even when one of the plaintiff’s dismissals was by agreement. The court rejected Great Lakes’s appeals to the “purposes” of res judicata doctrine, which the court said couldn’t supersede the Rule’s language. The court also rejected Great Lakes’s suggestion that it couldn’t reconsider the Montana court’s conclusion, reasoning that it was “well within [its] discretion to correct ” that decision because it “was wrong” and because no final judgment had been entered. Id. at 14 n.20.

This is Great Lakes’s appeal. 1

II

We must decide whether, under Rule 41(a)(1)(B), Great Lakes’s second voluntary dismissal foreclosed further litigation of its declaratory-judgment claim, such that summary judgment in

1 We review de novo a district court’s summary judgment order and its inter-

pretation of the Federal Rules of Civil Procedure. Amerisure Ins. Co. v. Auchter Co., 94 F.4th 1307, 1310 (11th Cir. 2024) (summary judgment); Hemispherx Biopharma , Inc. v. Johannesburg Consol. Invs., 553 F.3d 1351, 1360 (11th Cir. 2008) (Federal Rules).

23-12020 Opinion of the Court 7

favor of the Crabtrees was proper. We hold that it did and, therefore , that it was.

A

“Rule 41(a)(1) means precisely what it says,” Est. of West v.

Free access — add to your briefcase to read the full text and ask questions with AI

Great Lakes Insurance SE v. Bryan Crabtree, (11th Cir. 2026).

Great Lakes Insurance SE v. Bryan Crabtree (Great Lakes Insurance SE v. Bryan Crabtree) — published by Counsel Stack Legal Research, free access to 12M+ legal documents.

Related