Tom made his first skydiving jump with family friend, Jack Snyderman's son. Tom's father was a paratrooper in the 82nd Airborne of the US Airforce during World War II. After returning from the war, Vinnie and his friends pioneered the sport of skydiving in New England as a recreational activity. Henceforth all the Silvia children and beyond have been skydiving including Tom, who enjoyed countless freefalls throughout his life.