1962 Preakness was tip of the iceberg for Jolley at Pimlico

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Hall of Fame trainer LeRoy Jolley was a major presence on the racing scene for more than three decades, training a handful of champions and winning the Kentucky Derby with Foolish Pleasure in 1975 and the filly Genuine Risk in 1980.
Although he has not started a horse since 2012 or trained a winner since 2010 (according to Equibase statistics), Jolley comes to mind this Preakness week as the Baltimore classic proved an unusually difficult hurdle for the great horseman at the peak of his career.
As best as I can determine delving into the Preakness media guide and other reference material, no trainer in modern times has saddled more losing favorites in the Preakness without ever actually winning the race. In addition to the second-place finishes of his two Kentucky Derby winners, Jolley also trained 1976 Preakness favorite Honest Pleasure, who wilted to fifth after a pressing a hot pace set by Bold Forbes.
Jolley, who had a collective seven Preakness starters, came closest to winning with his first starter in the race, Ridan, in 1962. Only in his mid-20s at the time, Jolley trained Ridan to major wins in the Arlington Futurity, Washington Park Futurity, Florida Derby, and Blue Grass by the time the Preakness rolled around.
After a third-place finish in the Kentucky Derby, Ridan started at 2.70-1 in the Preakness, as did eventual Belmont winner and divisional champion Jaipur, who is recognized as the actual post-time favorite. It was a stifling hot day at Pimlico, with temperatures in the 90s and a pre-open infield crowd of more than 33,000 on hand.
While Jaipur would fare poorly in the Preakness, finishing 10th, Ridan looked for much of the final furlong as if he would gut out a narrow victory over the tenacious Greek Money, a near 11-1 chance whose biggest win to that point had been the $28,000 Chesapeake at Laurel a month earlier. Watching film of the race, it’s incredible how Ridan gave up the ghost in the final yards (press play and click the link).
Manny Ycaza, aboard Ridan, claimed foul against Greek Money and jockey John Rotz. As Whitney Tower recounted in Sports Illustrated:
This was a high show of gall, but the track stewards took Ycaza's claim under consideration as they studied the film patrol immediately after the race. The film was a revelation.From the time Ridan bore out slightly while leading around the final turn into the stretch -- an odd move by Ycaza that permitted Rotz to sneak through on the inside -- the pair of them left the field behind and fought it out alone. The lead then changed hands at least three times. At the sixteenth pole Ridan was in front by a neck. At the 70-yard pole they were dead-heated. It was there, claimed the indignant Ycaza, that "Greek Money came out and bumped me." The camera said no.
"In the last three strides," Rotz remarked afterward, "I thought I was finished. I had done everything I could and still couldn't get by Ridan. As we hit the wire I gave it everything I had. I threw myself and my reins with every ounce of forward thrust."
What was Ycaza doing then? The camera showed that he had taken matters into his own hands -- or at least into one of them. He had leaned over on Rotz and shot his left elbow squarely into John's chest. Rotz was lucky to have avoided a nose dive over the rail just as Greek Money nosed over the line.
For his brash claim of foul and his disgraceful attempt against a fellow rider, Ycaza was set down for 10 days, and this penalty may be increased. Had he won the race he would have been disqualified.
More than a half-century later, the 1962 Preakness remains one of the more memorable editions in the race's history. Unfortunately for LeRoy Jolley, it was the beginning of a streak of disappointment at Old Hilltop in a race that ultimately eluded him.
(1962 Preakness photo: Joe DiPaolo Jr./Baltimore Sun)
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