Kieran W. Leary

Kieran is a Partner at Tollefson Bradley and has established himself as a preeminent attorney in first party property litigation. Mr. Leary focuses his practice on complex and high-exposure claims under homeowners, commercial property, builders’ risk and commercial inland marine policies. Kieran has prevailed at trial and in several insurance coverage appeals of first impression before the Connecticut Supreme Court, United States Court of Appeal for the Second Circuit, and United States Court of Appeal for the Fifth Circuit.

Mr. Leary has obtained numerous important trial court and appellate decisions in COVID-19 business interruption, hail, hurricane, burst pipe, special investigation unit (SIU), appraisal, fraud, and freeze damage claims and lawsuits.  Carriers have frequently chosen Mr. Leary to represent them in their most challenging post-appraisal and first party property coverage matters, including routinely transferring such matters to him from their prior counsel.

Kieran served as lead trial and co-appellate counsel in the seminal Connecticut Supreme Court case, Karas v. Liberty Ins. Corp., 335 Conn. 62, 228 A.3d 1012 (2019), which resolved the crumbling foundation “collapse” litigation decisively in favor of carriers—an upset victory that saved the insurance industry over $2 billion. He additionally successfully served as lead trial and appellate counsel in Dino v. Safeco Ins. Co. of Am., which was identified by Law360 in its top daily story as one of “4 Insurance Battles to Watch at State High Courts” in Fall 2019. Dino concerned the appropriate trigger of coverage for a supposed progressive first-party property loss.

Mr. Leary is a frequent speaker to carriers and trade groups on insurance-related issues, including the latest developments and trends in appraisal and first-party claims in Texas. Additionally, his cases and analysis have frequently been featured in Law360 and Claims Journal’s top daily stories.

Kieran graduated cum laude from the University of Maryland, College Park, where he finished in the top 10% of his graduating class, was a Dean’s Honor Scholar, and a Graduation Speaker Finalist. He attended the University of Miami School of Law before graduating from the Florida International College of Law, where he finished in the top 10% of his graduating class.  

Mr. Leary credits his upbringing and proven dedication to his community as key components to his unique coverage perspective that has led to his success in practice. He was raised between the East Mt. Airy/Germantown section of Uptown Philadelphia, Pennsylvania and Spring, Texas. He dedicated his summers in college to educational and literacy outreach efforts in Philadelphia’s most impoverished and crime-afflicted neighborhoods on behalf of the Philadelphia Phillies baseball club. In further service to his community, Kieran began his career as a public defender in Tampa, Florida before his transition to private practice.