It’s been quite a ride for Gary Contessa. After 35 years as a thoroughbred racehorse trainer, Contessa, who grew up in Merrick, decided it was time — not to retire, but to close one chapter of his career.
“I’ve had a heck of a run as a trainer and I want to get into the management side or racing,” he said. “I feel I can do a lot of good, either at a smaller track or one of the larger circuits.”
The 62-year-old saddled his last of 18,148 career starts on March 21 at Tampa Bay Downs when Shandian placed fifth. He finished with 2,364 victories, 2,489 seconds, 2,466 thirds and accumulated more than $84 million of totaled earnings with an overall win success rate of 13 percent.
“Nobody in my family had a background with horses, but I took to them at a young age,” Contessa said. “When I was about 10-years-old, I rode my bike from Merrick to Hempstead Lake State Park and cleaned stalls in exchange for a one-hour horse ride.”
Soon after graduating Calhoun High School in 1975, Contessa literally knocked on barn doors at Belmont Park asking trainers for work. He began hotwalking for David Sazer, and after a few years became a groom for Jimmy Picou. Then, in 1980, Hall of Fame trainer Frank Martin offered Contessa double his previous salary to become his top assistant.
“I found out early that it’s a great business to advance yourself,” Contessa said. “I’ve always worked hard. Being with Frank Martin gave me the opportunity to learn from one of the greatest horsemen in the world.”
After five years with Martin, Contessa’s time to open his own barn arrived. His journey as a trainer began in 1985 at Monmouth Park in New Jersey. The first of his 23 wins that year came on June 8 when his debut starter, Legendary Wealth, cruised to victory. “It was a big deal to win that first race under my name,” he said.
From 1986 to 1993, Contessa trained for Bright View Farm and dominated the New Jersey circuit. He began training full-time in New York in the winter of 1993, and at his peak had a 150-horse barn and five assistants.
From 2006 through 2008, Contessa led all New York Racing Association trainers in wins. In 2007 he set a single-year record with 159 victories, breaking a mark previously held by Martin. The following year, Contessa broke his own record by saddling 178 winners. “I had mixed emotions about breaking Frank’s record,” he said.
A two-time NYRA Trainer of the Year, Contessa’s top horses of all-time include Grade 1 winners Sippican Harbor and Do It With Style, 2014 Kentucky Derby runner Uncle Sigh, and multiple-graded stakes winners Rite Moment, Mission Approved and True Affair.
His trip to the Derby with Uncle Sigh was a dream realized, he said. Making the experience even more memorable was the “Duck Dynasty” following for Uncle Sigh, who was named after one of the television reality series’ personalities, as well as mingling with the many guests of owner Chip McEwen’s Wounded Warrior Stables.
“I was in Kentucky for a week-and-a-half,” Contessa said. “Something I’ll always remember is walking alongside Uncle Sigh on the way to the track. There attendance was about 165,000, and I spotted a whole section of people dressed up like the guys from Duck Dynasty. It was incredible.”
Contessa now lives in upstate Hoosick Falls.