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Derby Hopeful New York Product


For the second consecutive year, the north country has connections to a horse poised for a potential run on the Triple Crown trail.

Uncle Sigh, a New York-bred colt, is being pointed to the Kentucky Derby, to be run May 3.

The horse is trained by Gary Contessa, a regular on the New York racing circuit who is married to Watertown native Jennifer Conklin Contessa.

“We’re just really, really excited that he’s going to the Derby,” Jennifer Contessa said of Uncle Sigh. “We’ve had a couple of contenders the last three or four years, that didn’t quite make it.”

Entering Saturday’s races, Uncle Sigh was 17th in the Kentucky Derby rankings, which is based on a point system with about 20 spots available to qualify for the first leg of the Triple Crown.

Last May, the area saw connections to the Kentucky Derby.

Jockey Rosie Napravnik, who was bidding to become the first female to win the Run for the Roses, made the bid aboard Mylute. The jockey’s mother-in-law, Sara Escudero, was born and raised in Watertown.

The Contessas and Uncle Sigh’s other ties are hopeful the horse’s 24 points will be enough to secure a start in the Derby.

“This is so exciting,” Jennifer Contessa said. “My husband has been a trainer for about 30 years, and you don’t get the opportunity that often to go to the Kentucky Derby. This is big time, this is the best of the best.”

Gary Contessa led the nation in earnings and wins for four years (2006-09), including setting the single-season record for wins in New York with 159.

Uncle Sigh, a son of equine standout Indian Charlie, has placed in the money in four of his five career starts, including one first-place finish and three seconds.

After placing second in both the Withers and Gotham, a pair of Grade 3 stakes races at Aqueduct, Uncle Sigh was fifth on the same track last Saturday in the Grade 1 Wood Memorial, one of the traditional prep races on the road to the Kentucky Derby.

“He probably would have won, but we decided that he needed blinkers,” Jennifer Contessa said. “He had never been in post 10, never had to go across the field like that. So after the race we decided we had to put blinkers on him and go forward to the Derby.”

Jennifer Contessa, who will turn 40 later this week, lived on the family farm in Burrville before her family moved to Greenwich in Washington County when she was 12.

Contessa’s dad, David H. Conklin, currently lives in Watertown and her late grandfather Raymond Churchill was the former fire chief at the Town of Watertown Fire Department.

Jennifer Contessa met Gary Contessa at Saratoga Race Course in 1995 while she was in college, and they were married the next year. They now live on Long Island with their children Vincent, Joseph, Raymond, Elizabeth and Caroline.

“Gary has been to the Breeders Cup, he’s won a lot of stakes races and some big ones in New York and Maryland and Kentucky,” she said. “But this is Gary’s first horse in the Derby on his own. And if our horse runs well in the Kentucky Derby, then we’ll move on to the Triple Crown.”

Uncle Sigh is owned by Wounded Warrior Stables and Anthony C. Robertson, who donates a percentage of the horse’s earnings to the Wounded Warrior Project.

The colt has generated comparisons to Funny Cide, owned by the Sackets 6 ownership group out of Sackets Harbor, which became the first New York-bred horse to win the Kentucky Derby and then the Preakness Stakes, in 2003.

“A lot of people have already said that Uncle Sigh reminds them of Funny Cide,” Jennifer Contessa said. “Because he has just this really chilled demeanor and he’s fun to be around.”

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