Leesfield & Partners Marks 50 Years Representing Monroe County Families

Leesfield & Partners marked its 50th anniversary on Feb. 18, 2026, reaffirming a five-decade presence representing families, residents and visitors from its Old Town Key West office at 615-½ Whitehead Street, directly across from the Monroe County Courthouse. Founder and managing partner Ira Leesfield remains at the helm as the firm highlights its continued work in Monroe County and the Florida Keys.

Ira Leesfield traced his motivation to a childhood moment that shaped his career. Leesfield said, "I was sort of thrust into the law by an eviction notice on my mom’s apartment when I was about 12 years old. We couldn’t afford the rent, and she was a single mom with three children … My mom was standing there in tears, and I said to myself, ‘this is not the place I want to be for the rest of my life.’ I wanted better circumstances and to help others get to a better place as well." Leesfield is now in his 50th year as a member of The Florida Bar.

The firm’s materials list a wide range of practice areas tied to local needs, including boating and recreational water-activity cases throughout Florida, motor vehicle and pedestrian crash representation, negligent security at resorts, sexual-assault and abuse cases, premises liability, defective pier wrongful-death claims, scooter cases and truck-versus-bicycle collisions. The firm’s published figures cite major jury results and settlements in Monroe County and Key West such as a $40.5 million negligent security/resort verdict, a $5.35 million truck/bike result, a $3.3 million premises liability verdict for paraplegia, and a $2.95 million defective-pier wrongful-death verdict.

Leesfield & Partners continues active litigation in the Keys. The firm filed suit on behalf of a man who was ejected from his bicycle after a crash on Stock Island involving a commercial truck driver; trial attorney Bernardo Pimentel II said, "This driver’s one moment of inattention has left my client with life-altering injuries," adding, "This frightening incident has left him in severe pain, causing a disruption to his daily life and happiness."

Road-safety work is a prominent local focus. State counts referenced by the firm show that as of Feb. 4, 2026 there had been about seven bicyclist-involved crashes and six pedestrian-involved crashes in Monroe County. The same state data record 161 bicycle crashes in 2024 with one death and 60 pedestrian crashes with at least two deaths; a separate year described as "last year" lists 133 bicycle crashes with three deaths and nearly 50 pedestrian crashes with at least three deaths.

Community involvement and philanthropy figure heavily in the firm’s local profile. The Leesfield Family Foundation, summed up by the motto "generosity, warmth, and reassurance," has partnered with World Central Kitchen and provided relief for the 2025 California wildfires, Hurricane Milton 2024, Hurricane Helene 2024, Hurricane Harvey 2017, the Pulse nightclub shootings 2016 and Hurricane Sandy 2012. Locally the foundation supports the Florida Keys Outreach Coalition and the Star of the Seas Foundation, and firm materials note sponsorships of the Marques Butler Memorial Softball Tournament, the 28th Annual Conch Fritter Celebration and Seminar held at 615-½ Whitehead Street, and past sponsorship of the Monroe County Bar Association’s "Justice for All Crawl." The firm also received a Historic Building Renovation Award from The Florida Bar for its Old Town office design.

Leesfield & Partners lists a Florida hotline at 800-836-6400, email Leesfield@Leesfield.com and the website Leesfield.com for people seeking help. Reflecting the firm’s charitable emphasis, Leesfield said, "it is not success if you just keep it all for yourself. You get no gratification out of that," and added, "I think what my colleagues are missing - those who have prospered - is how much you can do with so little. It doesn’t take a million dollars to make a difference," noting that "contributions of $5,000, $10,000, $20,000, $50,000 might seem insignificant to some of his peers, but 'to the people who need it, it means a whole lot.