Unlike many in the industry, Gary Contessa was the first in his family to show an interest in horse racing. Contessa began his career with Stanley Hough at Harbor View Farm before going to work for Hall of Fame trainer Frank “Pancho” Martin on the New York circuit.

Contessa would later start his own stable where in 2007 he broke his mentor Martin's record for number of victories at NYRA tracks with 159. Contessa has captured training titles at 12 individual NYRA meets and has amassed more than 2,300 career victories. He also serves as president of the Exceller Fund to aid retired Thoroughbreds.

Contessa has campaigned graded stakes winners including Rydilluc and Eightyfiveinafifty and Rite Moment. His first Grade 1 winner was 1991 Ashland Stakes winner Do It With Style and he earned his second 27 years later when Sippican Harbor won the Grade 1 Spinaway Stakes in September 2018 at Saratoga.