04/27/2004 11:00PM

Bailey blazes his own Derby trail

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LEXINGTON, Ky. - In 1982, Jerry Bailey picked up his first Kentucky Derby mount. New Discovery rounded out the mutuel field, never got closer than 10th, and beat one horse while Gato Del Sol and Eddie Delahoussaye took the roses.

Bailey, at 24, was on his way to New York to make it big. His Derby horse's name had not escaped his imagination.

"I hoped it would be one, but it didn't quite pan out," Bailey recalled in the Keeneland jocks' room on closing day of the spring meet. "He was a longshot at best, but I was glad I rode a horse like that because it's a lot to take in. Like they said, chills went down my spine when they played 'My Old Kentucky Home.' It was a great experience, and I couldn't wait to get back."

That would take another five years. Bailey finished ninth on longshot Conquistarose in 1987. A year later, 27-1 Proper Reality gave him a taste of having a live horse when he flashed into second at the eighth pole. But Winning Colors kept running, and Proper Reality faded to fourth.

Bailey skipped the next two Derbies and arrived with his first legitimate chance in 1991. Hansel went off the favorite but was evidently waiting for the Preakness and finished 10th. A year later, second-choice Technology was through leaving the backside and wound up 10th.

In 1993, Bailey's chances didn't look any better. Longtime client Mack Miller had Champagne winner Sea Hero for the Derby, but the colt had suffered through a dismal winter.

"I spent two months prior to the Derby trying to find a better mount, looking everywhere," Bailey said. "I just thought, 'He can't be the one.' I simply didn't have any options so I rode him. Lo and behold, it was meant to be."

Sea Hero went through traffic as if he were pulled by a magnet, and it was the last time Bailey didn't have a choice in the Derby.

One year later, Bailey picked Blumin Affair instead of front-running winner Go for Gin. The next year he opted for Tejano Run over Thunder Gulch and gave Gary Stevens his second Derby winner when Thunder Gulch won at 24-1. Bailey got the decision right in 1996, when he partnered Grindstone to a nose victory.

After that, rides on Phantom on Tour, Cape Town, and Worldly Manner made little impact. Bailey turned down 2002 winner War Emblem to ride Castle Gandolfo and can't remember if it's three or four winners that have slipped through his agent's book. Winning a Derby or two helps ease the pain of the ones that got away, but it's still the ultimate race for a jockey and an agent to handicap.

This year is no different. Bailey had the choice of Lexington winner Quintons Gold Rush, Fountain of Youth winner Read the Footnotes, and Louisiana Derby winner Wimbledon. Never mind bubble horse Eddington, whom Bailey would most likely choose if Pro Prado or one other dreamer stayed home.

"I wish I was three people, but I can only ride one," Bailey said of his choice to ride Wimbledon for trainer Bob Baffert. "It's an extremely hard race to pick right, and you have to pick right to win. Once you think you've picked right, everything pretty much has to unfold in your favor unless you're on way-the-best, which doesn't happen that often. The two I won, everything went my way."

Like so many Derby winners, Sea Hero and Grindstone had perfect trips, charging from the back. Of course, some Derbies are won on the front end. Others have been won by horses stalking the pace. There is no blueprint for picking the best horse or riding the perfect race.

"The two I won, I was doing things right - you have to pick the right horses to follow, and you have to pick the right times to go in and the right times to go out," Bailey said. "I hate to say this because I'll probably screw it up this year, but I think I've ridden every Derby without a mistake. I didn't always win, but I don't think I made a mistake."

Then Bailey stopped and remembered last year's draw. He chose the 12-hole for Empire Maker instead of the 5. He still wonders if losing ground on the first turn cost him the race.

Bailey has won two Derbies. He's in the Hall of Fame. He's earned more money than he can count. He believes he has never made a riding mistake in 16 Derbies. But just like a two-dollar bettor, his handicapping the Derby comes down to opinions, trends, and history.

"There's no crystal ball, but you just try and give yourself the best percentages," Bailey said. "Read the Footnotes is by Smoke Glacken. It's in the back of my mind that he might not go that far. Quintons Gold Rush - three races in a month. As much as you try to handicap horses to ride, you also have to handicap trainers. And, you know, Bob does well in the Derby."

Last year, Bailey won his seventh Eclipse Award and hinted that his time was running out.

"The chances are pretty good I'll be here next year," Bailey said. "Your mind frame doesn't change. You go into every Derby trying to make the right choice. Each one is so important that you never say, 'Oh I only have one, two, three years left.' They're all so important."