Jessica Kirkwood Alley


[email protected]

Phone: (813) 488-2924

Fax: (813) 488-2960

Success: To laugh often and much; To win the respect of intelligent people and the affection of children; To earn the appreciation of honest critics and endure the betrayal of false friends; To appreciate beauty; To find the best in others; To leave the world a bit better whether by a healthy child, a garden patch or a redeemed social condition; To know even one life has breathed easier because you have lived; That is to have succeeded. 

- Ralph Waldo Emerson



A litigator at heart, Jessica Alley thrives in the world of complex litigation. Jessica enjoys working with clients to develop and execute just the right litigation strategy for the client's particular need. She is equally at ease whether she is working side-by-side with in-house counsel, or leading the charge herself for an individual client. Jessica has focused her career representing clients in the insurance, legal, and healthcare industries.

Jessica's extensive insurance experience includes defending insurance agencies, MGA's, surplus lines brokers, and insurance professionals from errors and omissions claims. In addition to defending professional liability claims, Jessica has represented these professionals in contractual disputes with carriers involving underwriting guideline compliance and indemnity disputes under agency management agreements. She's also provided counseling to insurers construing insurance policies and has litigated numerous declaratory judgment actions on behalf of domestic and foreign insurers. Jessica's comprehensive experience helps her to understand the industry from a unique perspective.

Jessica also has extensive experience representing attorneys and law firms in defense of legal malpractice claims. She also has considerable experience defending healthcare companies in high profile and high-stakes litigation asserted under the False Claims Act and other federal statutes.

Based in Tampa, Jessica represents clients throughout Florida and beyond. She has litigated cases in state and federal court as well as private arbitrations. Jessica is a Partner in the Litigation Practice Group and a member of the Firm's Insurance/Reinsurance Industry Team. Before joining Freeborn, Jessica was a partner at Phelps Dunbar LLP.

Representative Matters

Representative Matters

  • Successful representation of agency in malpractice litigation involving COVID 19 (2022)

  • Obtained dismissal with prejudice for TPA in malpractice action (2021)

  • Successful representation of MGU in breach of contract and fiduciary duty arbitration related to alleged violation of underwriting guidelines (2021)

  • Successful representation of life reinsurers in YRT reinsurance rate disputes (2020)

  • Successful resolution of complex multi-state coverage litigation for domestic insurer (2018)

  • Obtained summary judgment for healthcare company in response to allegations of fraud under the False Claims Act (2016), which was affirmed on appeal (2017)

  • Obtained summary judgment for over $1 million dollars in costs and fees against adversary (2013)

  • Obtained a defense verdict in high profile, multi-million dollar legal malpractice trial, which was affirmed on appeal (2012)

  • Obtained judgment in favor of public company in two qui tam health care fraud actions under the False Claims Act (2009)

  • Obtained summary judgment in favor of an insurance agency on multi-million dollar claim (2006)

  • Obtained summary judgment in favor of insurer in declaratory judgment action (2004)

  • Obtained dismissal of insurance agency Pollywog Trans., Inc. v. Abest Agencies, 2004 WL 2673225, at * 1 (M.D. Fla. July 16, 2004)

Honors & Awards

Honors & Awards

  • AV® Preeminent Peer Review Rated by Martindale-Hubbell - Highest possible rating, 2016 - present
  • The Best Lawyers in America® - Commercial Litigation, Insurance Law, 2018 - present
  • Florida Super Lawyers – Rising Stars 2013-2014
  • Tampa Bay Business Journal – Business Woman of the Year (Finalist, 2009)

Professional Activities

Professional Activities

  • The Florida Bar, Appellate Practice Section and Trial Lawyers Section
  • Federal Bar Association, Diversity and Inclusion Subcommittee Member (2020 - 2021); Diversity and Inclusion Task Force Member (2019 - 2020)
  • Former Member, Florida Bar Grievance Committee (Chair, 2019)
  • Hillsborough County Bar Association
  • Hillsborough Association for Women Lawyers (Board of Directors, 2006 - 2007; Officer, 2007 - 2008)
  • Litigation Counsel of America
  • Professional Liability Underwriting Society
  • Defense Research Institute
  • ARIAS-U.S., Women’s Resource Committee Member (2020 - Present)

Speaking Engagements

  • Presenter, “Risky Business:  Legal Issues Confronting the Insurance Professional,” Clearwater, FL (February 2020) 
  • Panelist, “FAIA’s E&O 2019 Seminar,” Tampa, Florida (August 2019)
  • Panelist, Women in Law & Leadership Summit, Miami, Florida (March 2019)
  • Presenter, “Third-Party Bad Faith in Florida,” Chicago, IL (April 2018)
  • Presenter, "Florida Insurance Agent Standard of Care," Kansas City, KS (November 2015)
  • Presenter, "Discovery in an Electronic World," Chicago, IL (October 2015)
  • Presenter, "Third-Party Bad Faith in Florida," Chicago, IL (October 2015)
  • Tampa Bay Business Journal's Inaugural Bizwomen Summit, Mentor (8/22/2014) - (08/22/2014)
  • Presenter, "Discovery in an Electronic World," Kansas City, KS (June 2014)
  • Presenter, "Third-Party Bad Faith in Florida," Kansas City, KS and Chicago, IL (October 2012)