Leo Flanagan

Leo Flanagan, 57, of Gulf Breeze, Florida, passed away peacefully in his wife’s arms on October 10, 2025, after a brief battle with cancer. Born in Wilkes-Barre, Pennsylvania, Leo was an all-star athlete and proud U.S. Air Force veteran, serving as a radio operator at Andrews Air Force Base where he supported communications for Air Force One and Air Force Two.

Leo was known for his sharp wit, love of classic rock, spicy food, dogs, baseball, Mardi Gras, and his legendary karaoke performances. He had a big heart, a great sense of humor, and a quiet confidence that drew people to him.

He is survived by his wife, Darra Flanagan; parents, Leo and Elaine Flanagan; brother, Shawn Flanagan; children, Brittany (James) Clifton and Zachary Flanagan; and grandchildren, Emma, Ayden, and Hadley.

A visitation will be held Wednesday, October 15, from 5:00–7:00 PM at Roselawn Funeral Home in Gulf Breeze (Hawaiian shirts encouraged). A funeral service will follow Thursday, October 16, from 3:00–5:00 PM, with a reception and celebration of life at American Legion Post 378 beginning at 5:30 PM.

In lieu of flowers please donate to the Go Fund Me for Leo's wife, Darra https://gofund.me/e78ea7df6

OR to American Legion Post 378 - Gulf Breeze