Overview

Kaylee Chabarek is Senior Counsel in the firm’s Litigation & Dispute Resolution Practice Group, where she focuses on business and commercial disputes.

Prior to joining Trenam, Kaylee practiced at a boutique firm focused on complex insurance coverage, representing clients in state and federal courts, advising on bad faith exposure and avoidance, insurance coverage disputes, regulatory compliance, risk management, and litigation strategies across personal, commercial, and professional lines of insurance.

Kaylee also served as a Special Assistant U.S. Attorney, Administrative and Operational Law Counsel, and Trial Defense Counsel for the United States Army Judge Advocate General’s (“JAG”) Corps.

Kaylee’s diverse background in litigation, government service, and risk management enables her to provide clients with practical, strategic counsel in resolving complex legal disputes.

Representative Matters

  • Represented appellee in dispute over interpretation of a self-insured contract.
  • Obtained summary judgment in a federal court action addressing the applicability of coverage for a judgment in excess of 9 million dollars.
  • Obtained summary judgment in federal court on behalf of a client determining that a policy did not provide coverage for severe emotional distress.
  • Obtained final declaratory judgment in federal court addressing the applicability of the workers’ compensation and employer’s liability exclusions in a policy.

Honors and Distinctions

  • Florida Super Lawyers, Rising Stars, 2022-2024

Professional Involvement

  • American Bar Association
  • Florida Bar Association
  • Hillsborough County Bar Association
  • Florida Defense Lawyers Association
  • Association of Lawyers Defending Business (DRI)

Thought Leadership

  • Presenter, Interpleaders: A Safe harbor in the Storm, Florida Insurance Networking Symposium, August 15, 2025
  • Author, To Interplead or Not to Interplead: Best Practices in the Wake of Florida’s Tort Reform One Year Later. 43 Trial Adv. 40.
  • Author, Insurance Coverage for Attorney’s Fees Awarded Pursuant to the Offer of Judgment Statute or Based on Contractual Obligations Post Macedo, 40 Trial Adv. 28.