Walter "Sonny" Benedict Shaughnessy Jr.

Walter Benedict Shaughnessy Jr., known affectionately throughout his life by many names—including Sean W. B. O’Shaughnessy, Sonny, Uncle Sonny, and “GUS” (Great Uncle Sonny)—passed away peacefully at his home on Marco Island, Florida, on Wednesday, April 2, 2025 at the age of 80.

Born on June 23, 1944, in Dorchester, Massachusetts, Sonny was the cherished son of the late Walter and Marie Shaughnessy. A proud and decorated Army pilot, he served with honor during the Vietnam War. After his military service, he pursued his love of aviation becoming a commercial airline pilot, most notably, chief pilot with Marco Island Airways.

Sonny is survived by his loving siblings: Lee Ann “Annie” Shaughnessy of Naples, FL; and Jeanne Halferty of Lakewood, CO, and her husband, along with their daughter, Jocelyn Gurung, and granddaughter. He was preceded in death by his beloved younger brother, Mark Shaughnessy of Naples, FL, who passed away in 2024 after a brief and unexpected battle with cancer— a loss that left the family heartbroken. Sonny is also survived by Mark’s wife, Sue Shaughnessy, and their two sons, Ryan and Cullen Shaughnessy, and their respective families.

Sonny was deeply loved and admired by all who knew him. He was wicked smaht, could tell a hell of a war story, and was someone you wanted to sit and have a drink with. His dry wit and big heart will be remembered fondly by his family and friends.

There will be a Celebration of Life for Sonny on May 17th from 1:00pm to 4:00pm at one of his favorite places, Joey’s Pizza & Pasta House on Marco Island. In lieu of flowers memorial contributions may be made to the Tunnel to Towers Foundation at https://t2t.org/