Gotham Stakes: Vyjack gives owner first shot at Kentucky Derby

David Wilkenfeld has already made the score of a lifetime that most horseplayers can only dream about. In 2008, he had the sole winning ticket of a $3.3 million pick six at Santa Anita.

Five years later, Wilkenfeld is on the cusp of being able to live the dream that virtually every horse owner wants to experience. As the owner of Vyjack, Wilkenfeld has an undefeated 3-year-old who could be on his way to the Kentucky Derby.

Wilkenfeld will find out Saturday how much of a reality that dream could become when Vyjack faces his sternest test to date in the Grade 3, $400,000 Gotham Stakes at Aqueduct Racetrack. The winner of the Gotham earns 50 qualifying points to the Kentucky Derby, to be run May 4 at Churchill Downs.

“The opportunity to have a horse in the Kentucky Derby – as a longtime fan – you can imagine it’s a huge thrill, a dream I never thought could happen,” Wilkenfeld, 55, said. “We’re not that far off. I know everything has to go right. Just to have your horse in the Futures as one of 23, I feel like it’s a nice accomplishment.”

Vyjack, named after Wilkenfeld’s parents, Vivienne and Jack, was one of 23 individual horses offered by Churchill Downs in the first pool of the Kentucky Derby Future Wager on Feb. 8-10. Vyjack, trained by Rudy Rodriguez, closed at odds of 49-1, the 14th betting choice among 24, including a mutuel field that consisted of 346 horses.

Vyjack, a gelding, is the first horse Wilkenfeld purchased at auction. Wilkenfeld paid $100,000 for Vyjack at the Fasig-Tipton Midlantic sale of 2-year-olds in training last May at Timonium, Md.

Vyjack was the top choice on Wilkenfeld’s short list of potential purchases. Wilkenfeld worked with Sohby Sonbol, the former racing manager for Ahmed Zayat’s racing operation, in selecting Vyjack.

Wilkenfeld liked Vyjack’s pedigree – he’s by the Grade 1 stakes-winning freshman sire Into Mischief and is a half-brother to the multiple stakes-placed Prime Cut. Deeper in the pedigree is Miss Slewpy, the winner of the Ladies Handicap at Aqueduct in 1996, when the race was run at 1 1/4 miles.

Wilkenfeld was also impressed with Vyjack’s three-furlong workout in 34.40 seconds.

“This was the one I really wanted,” said Wilkenfeld, who had previously owned a few claiming horses. “It was early on in the sale, [and] I got him for the price I was willing to go to. I looked at some of the others, and I put a pretty tight budget on them, and they weren’t as exciting to me anyway. I wanted to get my feet wet. The rest, so far, has been a great ride.”

Wilkenfeld sent the horse to Bruce Jackson at Fair Hill to get him started. Vyjack was extremely studdish, according to Wilkenfeld, so Jackson recommended gelding the horse.

“You never want to geld a horse before you run him, but we spoke to the consignor, who confirmed what Bruce said about the horse [being aggressive],” Wilkenfeld said. “I’d rather have a racehorse that could do something than wait around and fight the horse. And he’s still aggressive. I listened to people who knew best.”

Wilkenfeld gave the gelding to Rodriguez to train. Wilkenfeld liked that Rodriguez didn’t have a lot of high-profile horses and that, as a former jockey, he got on many of his horses himself in the morning.

“He can get on your horse every morning; he’s been around the game a long time,” Wilkenfeld said. “I thought he would be a great guy to work with. With a one-horse stable, you don’t want to get lost in a big operation. The horse is a little difficult, as you can see in some of his races.”

Vyjack debuted Nov. 10 at Aqueduct, winning a 6 1/2-furlong maiden race by 1 3/4 lengths. Among those he beat were Clawback, who has since won two straight, including the Jimmy Winkfield Stakes, and Orb, who has since won three straight, including last Saturday’s Fountain of Youth Stakes at Gulfstream.

On Dec. 9, Vyjack won the Traskwood Stakes by 5 3/4 lengths over Always in a Tiz, who came back to lose by a neck in the Smarty Jones last month before finishing a well-beaten fifth in the Southwest on Feb. 18.

Vyjack made his two-turn debut in the Grade 2 Jerome on Jan. 5, winning by a head over a stubborn Siete de Oros. Vyjack showed how difficult he could be as he was trying to bear out under Cornelio Velasquez.

That led Wilkenfeld to make a rider change to Joel Rosario for the Gotham, an unorthodox move considering Velasquez was 3-for-3 on the gelding.

“I just think Cornelio is better with horses that aren’t as aggressive,” Wilkenfeld said. “I just felt they were fighting each other a little bit. I thought there were other guys that were a good fit, and when [Rosario] became available, I decided to make a change. It was not an easy thing to do. We had a lot of success together; it was just something I thought gave us our best shot to win going forward.”

That move illustrates Wilkenfeld’s mentality of not following conventional wisdom. He displayed that mentality five years ago when he put together a $4,320 pick-six ticket that included a 33-1 shot, Paparazzi Charm, who hadn’t been out in eight months and hadn’t won in two years. By virtue of that horse winning a claiming race, Wilkenfeld had the lone winning pick-six ticket worth $3.3 million.

“It didn’t change my life much, except it was a great moment in terms of all the efforts I put into handicapping,” Wilkenfeld said. “I was a little bit in shock; it didn’t sink in right away.”

Wilkenfeld made his play at the Meadowlands, where some friends of his were supposed to show but never did. In 2003, he had shared in a pick-six ticket worth $1.3 million at Churchill Downs.

Wilkenfeld grew up on Long Island, not far from Belmont Park, and began handicapping races from a young age. He would wager at the New York City OTB teletheaters in Manhattan, where he was introduced to Ragozin sheets.

In addition to his pick-six success, Wilkenfeld won $125,000 in the inaugural Breeders’ Cup Betting Challenge at Santa Anita in 2009.

Wilkenfeld, who is president of the online retailer Promgirl.com, said he believes the industry needs to offer more online handicapping contests with big prizes.

“Racing needs to adapt a little bit,” Wilkenfeld said. “If they do, they have great content. It’s a great sport. People need to change with the times and focus on a marketing opportunity where the bettor can wager a small amount of money but win big.”

Wilkenfeld, it seems, has been on a personal and professional winning streak. Five months ago, his girlfriend, Tanja, gave birth to the couple’s son, Nikola. Around the same time, Wilkenfeld purchased a Tribeca penthouse apartment that published reports said was on the market for $16.5 million.

“I got a 5-month-old son, a great girlfriend, a good business, and what looks like a really good horse,” Wilkenfeld said. “Life is good.”