Tale of Redemption for Jerry Bailey

Jerry Bailey, pictured after his final career race, overcame a battle with alcoholism to become one of the best riders in the country.
Jerry Bailey, pictured after his final career race, overcame a battle with alcoholism to become one of the best riders in the country. (Eliot J. Schechter/BloodHorse photo)

For anyone struggling daily against alcohol and substance abuse, no story can be more heartening than the fall and rise of Jerry Bailey.

Jerry Bailey

Birthdate: Aug. 29, 1957

Birthplace: Dallas, Texas

Career Record: 30,856 mounts, 5,893 wins, 4,554 seconds, 3,925 thirds

Career Purse Earnings: $296,113,529

Accomplishments: Won six Triple Crown races, 15 Breeders’ Cup races and four editions of the Dubai World Cup; amassed 216 Grade 1 victories and 16 New York riding titles; seven-time recipient of Eclipse Award as outstanding jockey; 1995 inductee into Racing Hall of Fame

In the beginning, when his thirst for alcohol led to long, unhappy nights that blurred into unproductive days, he appeared to be another average jockey eking out a living with equally ordinary mounts. When he finally tired of having his life ruled by drink, when he grew weary of the argumentative denials that shoved loved ones away, when he had enough of mediocrity and committed himself to sobriety with the help of Alcoholics Anonymous, he was transformed.

Raging arguments with his wife, Suzee, gave way to the love that always brought them back to each other. Now that hangovers no longer dominated his mornings, he awoke with energy and determination, eager to prove he was worthy of live mounts and could make the difference in the slight margins that typically separate winners from also-rans.

“Sobriety let the better side of Jerry Bailey, the kinder side, shine through,” Bailey said. “And I was able to get those mounts that I wanted.”

The physical gifts of the Dallas native combined with his intelligence and preparedness to elevate him into one of the greatest jockeys of any era with 5,892 wins and more than $295 million in earnings in a career that stretched from 1974-2006. He won six Triple Crown races, taking the Kentucky Derby, Preakness, and Belmont Stakes twice each.

He brought home 15 winners in the Breeders’ Cup World Championships. He was honored with the Eclipse Award as the outstanding jockey in North America an unprecedented seven times. He was inducted into the Racing Hall of Fame in 1995.

Bailey thinks he won many a race before they entered the starting gate. He prided himself of being ready for anything and everything in a delightfully unpredictable sport in which anything and everything regularly occurs.

Bailey after winning the Kentucky Derby aboard Sea Hero.
Bailey after winning the Kentucky Derby aboard Sea Hero. (Anne Eberhardt/BloodHorse photo)

“I not only handicapped horses. I handicapped riders,” he said. “I felt I knew what any rider would do in any situation. Granted, I might have been wrong sometimes. But I was right a lot more than I was wrong.”

His pursuit of success in the Kentucky Derby illustrates the complexity of that quest. As his reputation as a big-money rider grew, owners all but lined up to offer him their top 3-year-olds on the first Saturday in May. Making the correct choice was not easy.

“I won two,” Bailey said of his triumphs with Sea Hero in 1993 and Grindstone in 1996. “I chose wrong four times. Four horses I chose not to ride went on to win.”

The difficulty of winning the Derby only deepened Bailey’s appreciation for an event that causes many to push the pause button on their lives for two electrifying minutes.

“It’s so hard to win. That’s why it’s so special,” he said. “You have to have luck. Your horse has to be on his game. You, as a rider, have to be flawless.”

It seemed that the biggest of races allowed Bailey to take his game to an even higher level. Of his 15 Breeders’ Cup wins, five came in the Classic. Three of those occurred in successive years, from 1993-’95. He took the Dubai World Cup an unprecedented four times, in 1996, 1997, 2001, and 2002.

He lists the inaugural running of the World Cup — and his triumph with Cigar on an international stage half a world away — as one of his finest accomplishments.

Bailey and Cigar win the Dubai World Cup.
Bailey and Cigar win the Dubai World Cup. (Eclipse Sportswire)

“It was for America,” he said. “That was as close as I could ever get to being in an Olympiad.”

It was a fitting outcome, for Bailey embodies what America stands for: hope, opportunity and the unwavering belief that dreams can come true no matter how hard the ride.

Fun Facts

  • Bailey wrote his autobiography “Against the Odds: Riding for My Life,” with the author of this article. The book was published in 1995.
  • He followed Bill Shoemaker as Jockeys’ Guild President from 1989-’96.
  • He helped to introduce the flak jacket as a critical piece of equipment in helping to keep jockeys safe and places that among his most significant contributions to the sport.
  • After his retirement, Bailey immediately established himself as a top racing analyst.
  • Bailey wrestled in high school because he was not big enough to play football.

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