Billed the most extraordinary “Old-Timers’ Day” in the history of sport, The Living Legends Race on October 18, at Santa Anita Racecourse, will feature eight Hall of Fame jockeys with combined earnings of over $1.5 billion, as a prelude to the following weekend’s Breeders’ Cup.

The allowance will be contested at a sprint distance, and each rider’s mount, a California-bred selected by draw, will be assigned 126 pounds. The competing jockeys will be Angel Cordero Jr., 65; Jacinto Vasquez, 64; Sandy Hawley, 59; Pat Day, 55; Chris McCarron, 53; Jerry Bailey (pictured), 51; Gary Stevens, 45, and Julie Krone, 45.

“I’d be surprised if we ever see the likes of this gathering again,” Bailey said. “The total number of our wins and purse money takes your breath away.”

When Pat Day announced his retirement in 2005, he was the all-time money earner with $297,912,019, as well as a four-time Eclipse Award winner with victories in 12 Breeders’ Cup races, including four Classics and nine Triple Crown events.

Chris McCarron, who last rode to the post in 2002, as racing’s leading money-earner, won nine Breeders’ Cup races, including five Classics,  during his 28-year career, and claimed six Triple Crown events.

Sandy Hawley rode for 31 years, until his retirement on July 1, 1998. After apprenticing in Canada, he moved to the U.S. where he led all jockeys in victories in 1970, 1972, 1973 and 1976. He became the first jockey to ever win 500 races during a single year, when he broke Bill Shoemaker’s record in 1973. 

Jerry Bailey retired on Jan. 28, 2006 with 15 Breeders’ Cup victories, the most of any rider in history. He won each of the Triple Crown races twice and took four of the first 10 runnings of the Dubai World Cup, including the inaugural running aboard Cigar. He also rode Cigar to tie racing’s record for consecutive victories (16) in 1996. He is currently a racing analyst for ABC Sports and ESPN.

Jacinto Vasquez, who retired in 1996, won a pair of Kentucky Derbys (Foolish Pleasure, 1975, and Genuine Risk, 1980), but might be best known as the regular rider of the great filly Ruffian. He chose to ride her over Foolish Pleasure in their historic match race on July 6, 1975, when Ruffian broke down.

At the age of 30, in 1993, Gary Stevens became the youngest jockey to surpass $100 million in earnings. He reached the winner’s circle in eight Triple Crown events, including the three times in the Kentucky Derby, was victorious in eight Breeders’ Cup races, and won the Santa Anita Derby a record nine times. Stevens retired in 2005 and currently works as a racing commentator for NBC Sports and HRTV.

Julie Krone, the only female rider inducted into racing’s Hall of Fame, became the first woman to win a Triple Crown event, when she claimed the 1993 Belmont Stakes aboard Colonial Affair. She remains the only female to ride in the Belmont, having done so five times. She also is the only woman rider to capture a Breeders’ Cup race.

Angel Cordero won six Triple Crown races and four Breeders’ Cup events, and was the leading rider at Saratoga for 13 seasons.

Race victories and mount earnings of the riders during their active careers: Day, 8,803 and $297,912,019; McCarron, 7,141 and $263,985,505; Cordero, 7,057 and $164,570,227; Hawley, 6,449 and $88,681,292; Bailey, 5,893 and $296,104,129; Vasquez, 5,228 and $85,754,115; Stevens, 4,888 and $221,207,064, and Krone, 3,704 and $90,125,644.