WESTCHESTER SURPLUS LINES INSURANCE COMPANY v. PORTOFINO MASTER HOMEOWNERS ASSOCIATION INC

CourtDistrict Court, N.D. Florida
DecidedSeptember 22, 2025
Docket3:23-cv-00453
StatusUnknown

This text of WESTCHESTER SURPLUS LINES INSURANCE COMPANY v. PORTOFINO MASTER HOMEOWNERS ASSOCIATION INC (WESTCHESTER SURPLUS LINES INSURANCE COMPANY v. PORTOFINO MASTER HOMEOWNERS ASSOCIATION INC) is published on Counsel Stack Legal Research, covering District Court, N.D. Florida primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
WESTCHESTER SURPLUS LINES INSURANCE COMPANY v. PORTOFINO MASTER HOMEOWNERS ASSOCIATION INC, (N.D. Fla. 2025).

Opinion

UNITED STATES DISTRICT COURT NORTHERN DISTRICT OF FLORIDA PENSACOLA DIVISION

WESTCHESTER SURPLUS LINES INSURANCE COMPANY, et al.,

Plaintiffs,

v. CASE NO. 3:23cv00453-MCR-HTC

PORTOFINO MASTER HOMEOWNERS ASSOCIATION, INC, et al.,

Defendants. _________________________________/

ORDER This action arises from Hurricane Sally, which slammed into the Gulf Coast on September 16, 2020. At the center of this dispute is a $187 million insurance appraisal award ostensibly reflecting the storm damage sustained by a collection of Pensacola Beach condominiums, colloquially known as the Portofino Towers. Plaintiffs, thirteen commercial property insurers (collectively, the “Insurers”),1 broadly request that the Court either declare the award invalid and unenforceable

1 The Plaintiffs are Arch Specialty Insurance Company (“Arch”), Aspen Specialty Insurance Company (“Aspen”), AXIS Surplus Insurance Company (“AXIS”), Colony Insurance Company (“Colony”), Evanston Insurance Company (“Evanston”), Homeland Insurance Company of New York (“Homeland”), Independent Specialty Insurance Company (“Independent”), Interstate Fire & Casualty Company (“Interstate”), James River Insurance Company (“James River”), Lloyd’s of London (Consortium #9226) (“Lloyd’s”), Landmark American Insurance Company (“Landmark”), Maxum Indemnity Company (“Maxum”), and Westchester Surplus Lines Insurance Company (“Westchester”). Page 2 of 28

under the terms of their respective polices, see 28 U.S.C. §§ 2201, 2202, or vacate the award under Florida’s Arbitration Code, Fla. Stat. § 682.13. Defendants, the homeowners’ associations holding the insurance policies (collectively, “Portofino”),2 fiercely defend the award and bring counterclaims against the Insurers for breach of contract based on the Insurers’ refusal to abide by it. This has

culminated in twenty-two motions presently before the Court, accompanied by hundreds of pages of briefing and thousands of pages of exhibits,3 and a two-day evidentiary hearing on a motion to vacate the appraisal award, where the Court heard

hours of witness testimony and attorney argument. Ultimately, the Court concludes that the appraisal award cannot stand because it is undisputed that Portofino’s appointed appraiser, George Keys, did not fulfill his raison d’être: he never stated

2 Defendants named in this action are Portofino Tower One Homeowners Association at Pensacola Beach, Inc., Portofino Tower Two Homeowners Association at Pensacola Beach, Inc., Portofino Tower Three Homeowners Association at Pensacola Beach, Inc., Portofino Tower Four Homeowners Association at Pensacola Beach, Inc., Portofino Tower Five Homeowners Association at Pensacola Beach, Inc., and Portofino Master Homeowners Association at Pensacola Beach, Inc. 3 Specifically, the Insurers filed numerous motions for summary judgment on a variety of issues, ECF Nos. 236, 241, 245, 248, 251, 266; several Daubert motions, ECF Nos. 238, 239, 240; a renewed motion to vacate pursuant to Fla. Stat. § 682.13, ECF No. 257; and certain Insurers filed individual notices of joinder to some of those motions, ECF Nos. 258, 259, 260, 263, 264. Likewise, Portofino filed its own motions for summary judgment, ECF Nos. 246, 250, 255, 261, 262, 265; Daubert motions, ECF No. 232, 252, 253, 254, 256; and, most recently, a motion to strike certain testimony offered at the evidentiary hearing on the renewed motion to vacate, ECF No. 347. The Court has given careful and due consideration to each motion. CASE NO. 3:23cv00453-MCR-HTC Page 3 of 28

the “amount of loss” to Portofino’s property caused by Hurricane Sally as required by the applicable insurance policy provisions.4 The Court will therefore grant the Insurers’ motion for summary judgment on this score, the appraisal award will be declared invalid under the terms of the policies, and the parties will be ordered to conduct a new appraisal before a new panel. See ECF Nos. 251, 260, 263.5

I. Background6 When Hurricane Sally made landfall, Portofino insured its five condominium towers and other neighboring structures through the Insurers and other non-parties. See generally ECF No. 222; see also ECF No. 104-1.7 After the storm subsided,

Portofino submitted a claim for the damage to its insured properties, and the parties

4 In the long run, this may be a pyrrhic victory for the Insurers, as they acknowledge that Portofino’s claim for the damage caused by Hurricane Sally will survive notwithstanding the Court’s decision, but it is the result the law compels, nonetheless. See ECF No. 352. 5 As discussed in more detail below, the Court alternatively grounds its decision in Fla. Stat. § 682.13(1)(b)(3) and vacates the award. 6 Given the length and complexity of the factual and procedural history, and because the Court writes primarily for the parties, the background provided here is abbreviated to cover only those facts necessary to resolve the issue at hand and any obligatory context. The below facts are undisputed and viewed in the light most favorable to the nonmovants, Portofino. 7 The non-parties are three other insurers, Princeton Excess Surplus Lines Insurance Company, Endurance American Specialty Insurance Company, and Everest Indemnity Insurance Company, who were originally parties to this action, but dismissed their claims without prejudice pursuant to Rule 41 of the Federal Rules of Civil Procedure. See ECF Nos. 84, 85, 86. Recently, Evanston and Portofino notified the Court of a “settlement of all claims by and between” them. See ECF No. 366. To date, however, neither party has moved for or stipulated to a dismissal of their claims. CASE NO. 3:23cv00453-MCR-HTC Page 4 of 28

proceeded to appraisal in accordance with the policies when they were unable to agree as to the “amount of loss” caused by Sally. See ECF No. 246-4; ECF No. 246- 5; ECF No. 251-4.8 Subject to a few exceptions, which are not material for present purposes, the operative appraisal provisions state: APPRAISAL - If the Insured and this Company fail to agree on the amount of loss, each, upon the written demand either of the Insured or of this Company made within 60 days after receipt of proof of loss by the Company, shall select a competent and disinterested appraiser. The appraisers shall then select a competent and disinterested umpire. If they should fail for 15 days to agree upon such umpire, then upon the request of the Insured or of this Company, such umpire shall be selected by a judge of a court of record in the county and state in which such appraisal is pending. Then, at a reasonable time and place, the appraisers shall appraise the loss, stating separately the value at the time of loss and the amount of loss. If the appraisers fail to agree, they shall submit their differences to the umpire. An award in writing by any two shall determine the amount of loss. The Insured and this Company shall each pay his or its chosen appraiser and shall bear equally the other expenses of the appraisal and of the umpire. See ECF No. 104-1 at 33 (emphasis added).9 Each side appointed an appraiser who they believed to be “competent and disinterested.” The Insurers appointed Patrick

8 A number of the pending motions address “notice” and “participation” issues with respect to the appraisal process.

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WESTCHESTER SURPLUS LINES INSURANCE COMPANY v. PORTOFINO MASTER HOMEOWNERS ASSOCIATION INC, Counsel Stack Legal Research, https://law.counselstack.com/opinion/westchester-surplus-lines-insurance-company-v-portofino-master-homeowners-flnd-2025.