Updated on 09/16/2011 8:48AM

Sky Jack key to Gold Cup

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Milwaukee Brew and Kent Desormeaux after winning the Californian in June. They will try to catch Sky Jack in Sunday's Hollywood Gold Cup.

INGLEWOOD, Calif. - As Sky Jack bowls along in front in the early stages of Sunday's Hollywood Gold Cup, his trainer, Doug O'Neill, will alternate between watching the race unfold and the timer on the tote board.

If the fractions for the first half-mile are quick, say 22 and 45 seconds, it could doom Sky Jack. Slower fractions of 23 and 46 seconds would give O'Neill and owners Rene and Margie Lambert the hope that Sky Jack can lead his six rivals through the Gold Cup distance of 1 1/4 miles.

"I'd like to see a 23 and 46," O'Neill said. "I think that's realistic. Anything faster than that will take a race he may not have in him."

A year ago, the 6-year-old Sky Jack was recovering from knee surgery and had yet to undergo two colic surgeries which threatened his life. This year, after returning from a

14-month break between races, he has developed into a top contender for the $750,000 Gold Cup, which has drawn a field of seven.

The Gold Cup favorite will be Milwaukee Brew, the winner of the Santa Anita Handicap and Californian Stakes this year. Dollar Bill, second to Street Cry in the Stephen Foster Handicap at Churchill Downs on June 15, and Momentum, who was third behind Milwaukee Brew in the Californian on June 15, are contenders. All runners carry 124 pounds.

Dig for It, Out of Mind, and Macaneo will be longshots. A top-three finish by any of them would be a surprise.

"I don't know if he'll go the mile and a quarter, but I know he'll like the dirt," said trainer Roger Stein of Macaneo, whose five United States starts have been on turf.

Bobby Frankel, who trains Milwaukee Brew, fears that a front-running Sky Jack will be tough to catch.

"There's no speed to go with Sky Jack," Frankel said. "I'm not sure Milwaukee Brew can beat Sky Jack the way the track is playing."

Frankel is worried that the Hollywood Gold Cup will develop along similar lines as the Suburban Handicap at Belmont Park last Saturday, when E Dubai led throughout to beat the Frankel-trained Lido Palace.

"Look what happened with E Dubai," Frankel said. "Sky Jack will get the same trip."

Milwaukee Brew and Sky Jack met for the only time in March, and finished first and last in the 14-runner Santa Anita Handicap. In the Californian Stakes, Milwaukee Brew rallied from sixth on the final turn to deny Bosque Redondo by a head.

"He ran a very good race and made up a lot of ground in the last eighth of a mile," Frankel said.

The two wins have made Milwaukee Brew the top handicap horse on the West Coast this year.

Sky Jack has not started since winning the Grade 2 Mervyn LeRoy Handicap over 1 1/16 miles by

5 1/2 lengths on May 12, his third start and first win of 2002. He led throughout and was going away from runner-up Bosque Redondo at the finish to maintain his unbeaten record in four races on the main track at Hollywood Park.

The way Sky Jack won the Mervyn LeRoy indicates 1 1/4 miles is not out of the question for him.

"In the Mervyn LeRoy, if that was a mile and a quarter, he would have won," O'Neill said.

Earlier this year at Santa Anita, Sky Jack finished second by a nose in an allowance race in February, his first start in 14 months, before finishing last in the Santa Anita Handicap three weeks later. O'Neill blamed himself for the Big Cap loss, saying he would not ask the gelding for such a quick turnaround in the future.

With that in mind, O'Neill passed the Californian Stakes to focus on the Gold Cup.

"He's doing super and he seems to be on his toes," O'Neill said. "He's a horse I never school in the paddock. I just lead him over on the day of."

Sky Jack breaks from post 5 and will be ridden by Laffit Pincay Jr. Dig for It, who could be close early, is one post to Sky Jack's inside.

"I'm glad we're outside of Dig for It in case he goes," O'Neill said.

Having a top contender in such a lucrative race is new territory for O'Neill, whose stable consists mostly of claimers. A win by Sky Jack would be a career milestone.

"To have Bobby Frankel say he's scared of you, that's something to frame and put on your wall, win or lose," O'Neill said. "Hopefully, after a win."

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