Sean Edward O'Leary, 66, of Port Charlotte, FL - beloved husband of Diana (Dee) O'Leary (Klemba), passed away in his home Saturday, December 27, 2025. He was predeceased by his parents and brother Brian O'Leary, his in-laws Robert (Kenny) Klemba and Josephine Lane.

Born in Hartford, CT, on January 28, 1959, to Cynthia (Melvin) O'Leary and John Edward O'Leary. He grew up in Wethersfield, CT, with his parents and three siblings, Kevin, Brian, and Kathleen. Sean's impact began then, friendly to all and always "sticking up for little guy."

He played football as a Center at Wethersfield High, where he graduated in 1977. He continued his formal education at Springfield College for one year. His love of learning never stopped, and you would find him sitting with a large history book any chance he had.

He met the love of his life and center of his world Dee in 1980 and married her on June 8, 1985, at the Webb Barn in Old Wethersfield, CT. They bought their first home in Cromwell before settling into Colchester in 1989, where they lived for 21 years in a tight-knit neighborhood where he made lifelong friends.

They adopted their two children, Matthew and Chelsea, in 1993. He was an incredibly involved Dad who was there for everything his children did, both in presence and in loving support. He became a Papa in 2017 and threw all of himself into being a part of his grandchildren's lives.

Sean had an unmatchable work ethic. He worked for the Town of Wethersfield and The Old Town Cafe in his early years. The majority of his career was spent working as a telephone repairman. His coworkers became family at SNET. He got involved with the CWA union and fought passionately for what was right as a Steward and then Chief Steward. He ended his working days doing something he loved, greeting people and surrounded by baseball for Charlotte County at the Tampa Bay Rays training facility.

Sean loved sports, but his true character shined through coaching in youth sports. In the town of Colchester he spent 16 years coaching and volunteering. Baseball, soccer, Cougar Football, Bacon Academy Football, and the Parks and Recreation Commission. He cared deeply for all the kids- listening, supporting and being a role model. Everyone involved with him in those years knew his love for your families.

Sean continued his volunteer work helping start the Yellow Ribbon Commission in Colchester to honor the men and women in town who were actively deployed overseas.

After Sean retired and relocated to Florida, he finally had time to put towards another love, dogs. He began volunteering at the Animal Welfare League (AWL) of Port Charlotte, walking shelter dogs.

Sean is best known for his unwavering compassion for others. He was the man who would stop for strangers on the side of the road. The man who would hold your hand if you were afraid on an airplane. The man who would share tears for your loss. The man you could call for advice without judgement. The man who would reach out to you if a storm was coming to check if you needed help. The man who would give generously because "you can't take it when you go."

Sean was devoted to the ones he loved and to being kind to every person he met. The world was a better place with him in it. His legacy will live on in every life he touched.

He leaves behind his wife, Diana (Dee) O'Leary, his children Matthew O'Leary and Chelsea Siddiqui (O'Leary), grandchildren Diana & Cynthia Siddiqui and Noah & Lucas O'Leary, children-in-law, Farooq Siddiqui and Shannon O'Leary. Brothers-in-law, Bob, Ron, and Ray Klemba his very special Sister-in-law, Denise Klemba. His siblings Kevin O'Leary (wife Susan) and Kathleen O'Leary. Sister-in-law Lori O'Leary, several nieces and nephews, as well as many other family and friends.

We will be holding life celebration ceremonies in Florida and Connecticut.

Life Celebration Center of Punta Gorda

1515 S Tamiami Trail

Friday, January 2nd, 5-8 PM

Connecticut TBA

In lieu of flowers, the family is asking loved ones to donate to one of the charities Sean was passionate about to honor him.

AWL - Animal Welfare League of Port Charlotte https://www.awlshelter.org/

WWP - Wounded Warrior Project https://www.woundedwarriorproject.org/