Robert “Bobby” Ussery’s Story: A Living Legend in our Midst

In the month of May while the Kentucky Derby and the Preakness were happening, the Presidential Place team realized they had a living legend in their midst. He is Robert “Bobby” Ussery and he recently moved to the community. Mr. Ussery has 3,611 horse racing wins as a jockey, with a 17.5 winning percentage and ranks among some of the game’s best. He retired in 1974 and six years later, he was inducted into the National Museum of Racing and Hall of Fame.

Presidential Place senior living resident Bobby Ussery displays his mementos of his Kentucky Derby and Preakness Stakes victories in his community in Hollywood, Florida. (Bobby Ussery / Courtesy)

Disqualification at the Kentucky Derby

Mr. Ussery can speak to Medina Spirit’s disqualification at this year’s Kentucky Derby and the two-year suspension of Bob Baffert. Ussery experienced it himself. He was hoping to get two back-to-back Kentucky Derby wins, the most prestigious race in the country. In 1967, he rode Proud Clarion to victory and then in 1968 he rode Dancer’s Image across the finish line in first place. He found out days later that Proud Clarion had failed a drug test, which set off a lengthy court battle that came to an end in 1973.

Here’s Mr. Ussery’s thoughts on this year’s Kentucky Derby:
“He’s going to be disqualified,” Ussery said. “They’re not going to let this slide because it’s been in the news and everything and they don’t need this. Baffert’s saying this and that. I don’t know what happened — but something happened because he’s got a bad test and they can’t have that. Not after what they did in ’68.”


Kentucky Derby winner Bobby Ussery rode Proud Clarion to victory in 1967. (Bobby Ussery / Courtesy)

His Legacy

In 1935, Mr. Ussery was born in the tiny town of Vian, Okla., just west of Fort Smith, Ark. He grew up on a farm picking cotton and cutting vegetables. At the age of six, he started riding horses and soon after entering races on bush tracks. He started racing with a team in Texas, but his first stakes race came in 1951 at the Fair Grounds Race Course in New Orleans where he rode Reticule to victory in the Thanksgiving Handicap.

“He said let’s put Bobby on it. And I had never ridden on a major race track before. . .  and stuff like that. And the horse had 104 pounds, the horse won,” said Mr. Ussery. “And then the rest is history.”


By the end of the fifties, he had won the Travers, Whitney and Alabama Stakes. He had over 60 major racing wins, which included five wins in 1960, with three stand out wins at the Hopeful Stakes, the Florida Derby and the Preakness.

One of his most memorable races was riding Windfields Farm’s colt New Providence to a win in 1959 at Canada’s most prestigious race, the Queen’s Plate.

“Here’s a picture,” Ussery said, pulling out his phone to flash a picture with the queen. “She congratulated me. What am I? I’m a young kid. I don’t know what I’m going to say to a queen. I never met royalty before, and I don’t know anybody else would know what to say if you’re just meeting the queen the first time. She more or less talked to (the horse’s owner) E.P. Taylor, but I talked to her husband, Charles. I talked to him quite a bit. They had racehorses themselves. … Yeah, I did it all.”


Hall of Fame jockey Bobby Ussery astride Proud Clarion at the 1967 Kentucky Derby in Churchill Downs. (Bobby Ussery / Courtesy)

Welcome Robert “Bobby” Ussery to Presidential Place

Mr. Ussery says horse racing made him into the man he is today. He has survived triple bypass surgery and now he wants to let someone else do the chores. He has better things to do, like watch horse racing. The Presidential Place team is more than willing to oblige.

Josh Navarro of WPTV speaks with retired Hall of Fame horse jockey Bobby Ussery, who lives in South Florida in the senior living community Presidential Place, to get his opinion on life as a jockey and the upcoming Preakness Stakes race.

Source: Hal Habib, “Bobby Ussery, who saw 1968 Kentucky Derby win taken from him, sees no hope for Bob Baffert and Medina Spirit,” Palm Beach Post, n.p., May 10, 2021,

Source: Josh Navarro, “Former horse racing Hall of Fame jockey speaks about 146th Preakness Stakes,” WPTV News, n.p. May 15, 2021

Source: Emmett Hall, “Hall of Fame jockey Bobby Ussery maintains passion for horse racing,” Sun Sentinel, n.p., May 20, 2021