Photos provided.
Gary Contessa is perhaps one of the unique trainers at Saratoga Racecourse with a variety of experiences that go beyond being a horseman.
Along with having an impressive training career, Contessa has been a baseball hopeful, musician, and businessman, as well as making a significant move from Long Island to a more secluded area near the Vermont border.
Contessa has been training horses for nearly four decades. The 61-year-old Merrick native has been one of the top 10 trainers at Saratoga, including last year with eight winners, but he will admit it is not easy to win at Saratoga.
“It’s a tough place to win,” he said. “I know what I have to hit when I come up here. I do think I can hold my own up here. I think I will win some races and have fun.”
Contessa has been at the Oklahoma Training Track since May 15. While he would have preferred drier and warmer conditions this spring, he was running out of stall space at Belmont.
“I was getting too many horses at Belmont,” he said. “It was a good time to send horses up here, especially the young horses. Being a resident up here, I know when the weather is getting better for them.”
Since 2004, Contessa has been living in Hoosick Falls, about 30 miles east of Saratoga Springs. He and his wife Jennifer bought a 100-acre cattle farm that they converted into a horse farm.
“We wanted to escape the craziness of Long Island,” Contessa said. “We were in the market for a farm. Our real estate agent showed us a cattle farm in Hoosick Falls, but I had a vision of what we could make it.”
As the farm developed, Contessa got more horses, which meant investing more time downstate. The investment paid off with multiple training titles at Belmont and Aqueduct from 2005-2009, as well as breaking a New York record with 159 wins in 2007, which was previously held by his mentor Frank Martin (156 wins).
Contessa and Jennifer eventually had the farm certified as organic, sold it, and bought a home on approximately four acres in the Hoosick Falls mountains.
Today, Contessa is willing to travel a lot between Saratoga and Long Island because he enjoys living in the Hoosick Falls area.
“I am constantly on the road. I probably put 70,000 miles on a car each year,” Contessa said. “But I just love the town of Hoosick Falls. The area is quaint and the people are so genuine.”
For the Contessa, the travel is worth it. This year, he has 28 2-year-olds that include a pair being pointed to Saratoga’s opening week stakes races: Buxom Beast in the Schuylerville Stakes for fillies on July 11 and Theitalianamerican in the Sanford Stakes for the males on July 13.
Buxom Beast is an unraced filly who cost $205,000. Theitalianamerican, bought for $35,000, is still looking for his first win, but he has already made an impression on the track by finishing second in the Tremont Stakes.
Contessa is hoping at least one of his 2-year-olds can give him the success that Lee Pokoik’s now-retired Sippican Harbour did in winning last year’s Spinaway Stakes.
“Last year, I had a lot of success with the 2-year-olds,” he said. “In fact, I have had a good career with 2-year-olds. I love training young horses. I am meticulous about catching a problem before it becomes a big problem. ”
Contessa also resells horses who later have tremendous careers such as Peace Rules, a $35,000 purchase who later won seven graded stakes races and finished second in the 2003 Travers Stakes.
Today, Contessa has been helping Pokoik to resale horses, including an American Pharoah filly bought for $300,000, then sold for $600,000. Any horse they don’t resale becomes part of the racing stable, including Sippican Harbour who never sold for $100,000.
“It has been a very successful formula,” Contessa said. “We have put some good horses out there for other trainers to buy. My job is trying to make Lee Pokoik money. If Lee Pokoik makes money, he will be a happy owner and I will be able to keep doing this year after year.”
Contessa and his wife Jennifer also own Zero Gravity in Colonie. After going to laser tag several times in Saratoga several years ago, Contessa thought about building another facility.
“We found an unoccupied furniture warehouse that was perfect,” he said. “Of course, we’ve had some growing pains, but it was a success since Day 1.”
Contessa also plays bass and often appears at shows and fundraisers, including last year’s David Cassidy tribute concert to benefit the Thoroughbred Retirement Foundation. However, that’s not the only instrument Contessa has played.
He has played guitar, piano and saxophone while growing up in Long Island, an area known for emerging bands like Blue Oyster Cult. Contessa didn’t start playing bass until one of his early bands needed one.
“At the time, I was playing keyboards for this group, then we needed a bass player,” he said. “I thought, ‘I could do that.’”
Contessa has also been a session player and even a backup member for a 1950s revival show that featured Fats Domino and members of Frankie Lymon and the Teenagers.
Early in their partnership, Contessa and the late Cassidy never talked about music. It wasn’t until Contessa played at a fundraiser at the Saratoga Performing Arts Center where Cassidy discovered that
musical ability.
Over the years, Contessa, who admires jazz and funk bassists that include Stanley Clark, has played at other venues such as the Westbury Music Fair and B.B. King’s in New York.
“When I went to see David in concert, he was probably going to call me on stage,” Contessa said. “It was fun. His bass player would give me the bass and walk away.”
Along with being a musician, Contessa had been a solid pitcher at Calhoun High School in Merrick. At one point, he had considered a career in baseball, but chose to be a horse trainer.
While Contessa’s years of being a baseball player are far behind, he has shared some of those skills to his 12-year-old son Ray.
“I have given him a couple of pitches and some wisdom,” Contessa said. “I have taught him how to throw an off speed pitch. Every night, we go out and throw the baseball. I have batting cages so he can hit as well.”
Over the last four decades, Contessa has no doubts about his career and the decisions he has made about his life, especially with the amount of success he has had as a horseman.
“I have had a lot of fun with this over the years. It probably has helped me put my kids through college,” he said. “I have no regrets. I remain dabbling playing guitar for the last 40 years and training horses, and I am reliving my baseball life through my son.”
