Captain Gilbert Obituary

It is with profound sadness that we announce the passing of Captain Benjamin Jackson Gilbert Jr., affectionately known as Benjy, who died peacefully on January 15, 2025, surrounded by his beloved family. He was 76 years old. Benjy was born on February 17, 1948, in Charlotte, North Carolina, and spent his final years in Hernando, Florida.

His life was a testament to his passions, achievements, and the love he shared with those closest to him. Benjy was a devoted husband to his wife, Loretta, his beloved dog Rosie, and a loving and proud stepfather to Cherie Sanford (Jeff), Lori Miller (Daniel), and John Stacy Jr. (Whitney). He will be deeply missed by his grandchildren, Cierra Campbell, Skylar Torres (Adrian), Sophia Sanford (Rashawn Steppe), Logan Miller (Emily), and Bryson Miller (Morgan Heil). His great-grandchildren, Yasmina and Ysabella Torres, and Amiri Steppe, were a source of joy in his life. Benjy was also a loving brother to William Thomas Gilbert and Susan Elizabeth Gilbert, and was preceded in death by his parents, Benjamin Jackson Gilbert Sr. and Roberta Gilbert, and sisters June Gilbert Morrissey and Jacqueline Gilbert Stroupe.

Benjy was a veteran of the Vietnam War and served in the US Army from October 1969 to July 1971 as Fixed Crypto Repairman. He distinguished himself by receiving the National Defense Service Medal and Sharpe shooter M-14 award.

Benjy's educational journey began at Seminole High School, followed by the University of Florida, where he earned a Bachelor of Arts in Business Management.

His lifelong passion for aviation led him to an illustrious career as a pilot. Starting in 1965, he worked at Tampa Flying Service as a Line Service Technician and Flight Instructor. From 1972 to 1979, he served as General Manager and Chief Pilot, as well as Chief Flight Instructor, FAA Designated Pilot Examiner, and Check Airman. In 1979, Benjy's career soared when he joined Piedmont Airlines, which later merged with US Airways in 1989. He flew with the airline for over 25 years, receiving the prestigious FAA Team Spirit Award for his exemplary service. He retired from American Airlines as a Captain. In 2005, he continued flying with Polar Air Cargo, where he piloted freight flights to and from international hubs, further cementing his legacy as a skilled aviator.

Benjy was former President of Piedmont Silver Eagles and dearly loved his Piedmont family. In addition to his remarkable career in aviation, Benjy was an avid musician with a love for playing in the tradition of Hank Williams. He was also a dedicated fan of The Beatles, particularly their tribute band "1964 the Tribute." Benjy had a lifelong passion for sports, especially football, and was a devoted Georgia Tech fan, rarely missing a game. He also cherished the memories of attending the Mickey Mantle-Whitey Ford Baseball Camp, where he had the unique opportunity to play alongside baseball legends.

Benjy's other hobbies included flying as a private pilot, golfing, and volunteered at nursing homes where he entertained the crowds with his love of music. He enjoyed spending time with his friends, particularly tailgating at Georgia Tech football games, and was deeply committed to the people in his life, always offering kindness and support.

Benjy's life was one of love, passion, and fulfillment. He enjoyed a successful career, pursued his personal interests with enthusiasm, and, most importantly, created a legacy of love and devotion for his family. His enduring connection with his wife Loretta, children, grandchildren, and extended family was a source of great comfort and joy to him, and he will be deeply missed by all who had the privilege of knowing him.

A celebration of his life will be held on Saturday, March 8, 2025 at 1pm at his airline hangar at 7820 N Howard Hughes Way, Hernando, FL. In lieu of flowers, the family requests that donations be made to Tunnel to Towers Foundation. Rest in peace, Captain Benjy. Your love, wisdom, and joyful spirit will continue to inspire those who loved you.