Thomas James O'Leary

On March 25, 2026, Thomas James O’Leary, passed away peacefully at home, surrounded by his loving family, after a brave and courageous battle with colon cancer. Born in Washington DC, he was the son of the late William O’Leary and Mary (Thomson) O’Leary. Tom built a life centered on family, friendship, and community. He and his beloved wife, Jen, made their home in Annapolis, where they shared nearly 30 wonderful years together, creating a lifetime of cherished memories.

Tom was a proud graduate of the University of Maryland, where he earned his bachelor’s degree in business. He dedicated his professional life to helping others as a claims adjuster with Travelers Insurance, offering guidance to families during difficult times with compassion and integrity. Throughout his career, Tom also traveled on CAT duty across the country, offering comfort and steady support to those whose lives had been upended by natural disasters such as hurricanes and hailstorms.

Tom was a devoted sports fan who enthusiastically supported his local teams. From cheering on Terps basketball and football to following the Capitals, Redskins, and Orioles, his love for sports was truly all-encompassing. Affectionately known as “Tommy” by his closest friends, if a sports statistic was needed, he was the go-to guy. Tom also loved the outdoors camping or a simple hike and had a passion for the weather. From a quiet day watching golf to a crowd-filled day at a ballpark, Tom found happiness sharing life’s simple pleasures with others.

Above all, Tom was a family man. He treasured every moment spent with his loved ones and his wide circle of friends. His kindness, generosity, and warm spirit left a lasting impression on everyone who knew him. He had a remarkable ability to make others feel valued and cared for, and his presence will be deeply missed.

He is survived by his devoted wife of 29 years, Jennifer “Jen” O’Leary (née Tozzi); his loving children, James Joseph O’Leary and Laura “Laurie” Elena O’Leary; his cherished brothers, John Douglas O’Leary (Kathleen) and William “Billy” Edward O’Leary (Lisa); and his adored nieces and nephews, Mary Kate, Calum, Claire, John Jr., and Jenny; as well as beloved in-laws, family members and friends.

Tom will be remembered for his big heart, his unwavering love for his family, and the joy he brought into the lives of so many. He was deeply loved and will be forever remembered.

In lieu of flowers, the family kindly asks that you consider donating in Tom’s memory to the Colorectal Cancer Alliance, or directly to the funeral home to support a college trust that will be established for his children (you can reach out to the funeral home at 410-672-2200).

A Celebration of Life is planned for April 10, 2026, from 5:00 PM to 8:00 PM at the Whiteley Property Beach, 1738 Winchester Road, Annapolis, 21409. Note: This will be a casual outdoor gathering. For parking, turn at the stone entrance marked Severn Crest 1738.