Gary A. Caldwell Jr, 39, of Fishkill, NY, passed away on Friday, July 18, 2025, due to complications from an ongoing heart condition.

Gary was born in Poughkeepsie, NY, on August 29, 1985. He spent his childhood growing up on his family mountain in Fishkill, NY, where his Aunt Elizabeth Williams played a huge part in his upbringing and helped shape the man he became. He grew up riding quads and hunting on the mountain. His love of paintball began with his cousin James and lifelong friend Kyle; they spent countless hours in the woods before eventually becoming avid players who even competed in tournaments in and out of state.

Gary's love for motorcycles was unparalleled. He got his first Harley when he was 16 and could take any bike apart and rebuild it. His thrill for speed could scare even the most seasoned riders, and over the years, he rode through almost every state in the country. Gary also had a huge impact and presence in the MC world.

He began his work life at Clove Excavators doing blacktop. Driving soon became second nature, leading him to become a truck driver. Eventually, he and his wife started Tailgunner Trucking, Inc., where he proudly served as President and sole driver. Most recently, he worked for A&D Landscaping and became a Teamster with Local 456.

Gary met his wife, Sherry, in high school and fell in love with her the very first time they met. They married on September 27, 2014. Trips to Disney became some of their most cherished memories, where together they would share in the magical experience they loved so deeply. Together they had two children, Gatlin and Valen, who were his greatest pride and joy. More than anything, Gary loved being a father.

Gary is survived at home by his wife, Sherry, and their sons, Gatlin and Valen; his parents, Gary Sr. and Pamela; his sister, Jennifer; his nephew, Brendan and his girlfriend Olivia, and his cousin James, all of Fishkill; as well as numerous aunts, uncles, cousins, and countless friends. He was predeceased by his grandfather, Billy Brooks; grandmother, Irene Brooks; and his uncles, Joey and James Brooks.

Family and friends will gather to give Gary a proper sendoff on Sunday from 2-5pm at the McHoul Funeral Home, Inc., 895 Route 82, Hopewell Junction. There will be a time for sharing memories at 4:30 pm. Please feel free to attend on two wheels to continue his love of motorcycles. He was also a lover of Converse and P.F Flyers, his family would love to see your favorite pair.

In lieu of flowers, the family requests donations be made to a GoFundMe account for Gatlin and Valen. The funds will be placed into an account to be given to them when they reach adulthood, to help provide an extra step toward reaching their greatest potential. https://gofund.me/729299ec