Give famous jockeys enough time to ride enough horses, and they’ll inevitably become linked with one particularly memorable champion. Ron Turcotte had Secretariat. Eddie Arcaro had Citation. Earl Sande had Gallant Fox, and more recently, Calvin Borel had Rachel Alexandra.
In contrast, Bobby Ussery never achieved quite the same level of connection with a legendary horse, but that certainly didn’t stop him from being inducted into the racing Hall of Fame in 1980, just six years after his retirement. The reason? Ussery made a habit of winning lots of races, and lots of big races, on a wide variety of very good horses. Day in and day out, Ussery was simply a Hall of Fame-worthy rider.
Robert Nelson Ussery is his given name, though the formality of “Robert” quickly gave way to “Bobby,” a nickname that stuck throughout his career. Born in 1935, Ussery hailed from the little town of Vian, Okla., and spent a good portion of his childhood shining shoes and harvesting crops, earning money wherever he could to help support his large family. Eventually, that included riding horses, and while he would call New York home for the majority of his career, he started out less ambitiously — and indeed, less formally — down south.
The official records suggest that Ussery won the very first race he ever rode, guiding Reticule to victory in the 1951 Thanksgiving Handicap at Fair Grounds. But if it seems farfetched that a jockey could win a stakes race in his very first ride, maybe you’re on to something. Truth be told, he’d been riding for years, often for trainer Tommy Oliphant in Texas, at a time when official pari-mutuel races weren’t being held in Texas and racing was conducted on an unofficial grassroots basis.
As Dave Kindred wrote in the April 19, 1974, edition of the Courier-Journal: “At age 5 [Ussery] was first lifted onto a horse … at age 10 he rode Quarter Horses for $5 a race. At 14, he was galloping horses at Texas and Nebraska racetracks.”
And then Oliphant decided to give Ussery a shot at the big leagues.
“We went to New Orleans, and I rode him on a filly owned by King Ranch in the Thanksgiving Day Handicap,” explained Oliphant in an article published June 24, 2005, on Bloodhorse.com. “I took a lot of grief from well-known trainers for riding this kid nobody knew of. He took her to the lead, and she won by a head. That was the beginning of Bobby Ussery.”
It wasn’t long before Ussery made his way to New York and into the racing headlines. One of the first big-name horses he partnered with was the filly Bayou. Ussery was one of eight different jockeys to ride Bayou during her 1957 season, though no one else achieved quite the same level of success with her as Ussery, who helped Bayou secure champion 3-year-old filly honors by winning the Acorn Stakes and Maskette Handicap with strong rallies from off the pace.
Maybe Ussery had a way with riding fillies, because in 1958 he guided the future champion Tempted to victories in the Maskette Handicap and the historic Alabama Stakes, and in 1959 and 1960 Ussery kept his streak of success with fillies going with Quill, whom he rode to a series of clear-cut victories in the Acorn Stakes, New Castle Stakes, and Delaware Handicap. Later on, he helped forge the championship campaign of Straight Deal, who garnered champion handicap mare honors in 1967 after winning — among other races — the Bed o’ Roses Handicap and Delaware Handicap with Ussery in the saddle.
The 1960s certainly were the peak years of Ussery’s career, in large part because he started the decade with a banner year in 1960. In addition to his exploits about Quill, Ussery teamed up with the accomplished Bally Ache to win the Florida Derby, Flamingo Stakes, and Bahamas Stakes along the Kentucky Derby trail, and while Bally Ache could only finish second in the Derby itself (despite a bold front-running ride from Ussery), the colt rebounded to win the Preakness Stakes and stamp himself among the best males of his generation.
Still, arguably the most brilliant horse Ussery ever rode was unable to showcase his talent in the classics. That was Hail to Reason, an almost unstoppable colt who rattled off victories in the Youthful Stakes, Tremont Stakes, Great American Stakes, Sanford Stakes, Sapling Stakes, Hopeful Stakes, and World's Playground Stakes to be named champion 2-year-old male of 1960. Unfortunately, Hail to Reason’s career was cut short by injury, leaving racing fans — and surely Ussery as well — to wonder what might have been.
Many of Ussery’s victories came at Aqueduct in New York, where he was something of a living legend. A short note published in the Feb. 27, 1966, edition of the Hartford Courant told readers that “Bobby Ussery has developed the technique of easing his horses to the outside on the backstretch at Aqueduct and then gunning them down the banked turn. The spot now is known as ‘Ussery’s Alley.’ ”
“[Ussery] was among the first riders ‘to read the track,’ which is the way he discovered ‘Ussery’s Alley,’ ” wrote Seymour S. Smith in the April 28, 1979, edition of the Baltimore Sun. “Ussery noted that the water trucks and other equipment often left the huge storage tank near the five-eighths pole and then slanted down to the rail on the far turn. He reasoned the path must be fast, and if he had horse and post position, down the path he would go.”
Ussery’s skill at riding Aqueduct led to a memorable upset in the 1971 Brooklyn Handicap, in which Ussery used every bit of his strength and wit to guide Never Bow across the wire in first place. Jim McCulley, writing in the July 25, 1971, edition of the New York Daily News, called it “one of the most cunning rides ever given [to] a horse at Aqueduct.”
“Every New York horse fan knows about ‘Ussery’s Alley’ on the backstretch,” wrote McCulley. “Nobody, until yesterday, ever saw him pull the job on a long race in front of the stands like he did in the Brooklyn.” Ussery, nicknamed “Rapid Robert” due to his skill at riding front-runners, sent Never Bow straight to the lead, carried the favorite wide on the first turn, and convinced his mount to keep going through the testing drive to the finish line. “Ussery had a done-in horse under him for the final 50 yards,” described McCulley, “but somehow the Oklahoma rider held Never Bow together long enough to get the $69,060 first money.”
So of course, it’s slightly ironic that two of Ussery’s most famous rides came on deep closers in the coveted Kentucky Derby at Churchill Downs. Just days before the 1967 Kentucky Derby, Ussery — always ready to ride when given the call — picked up the mount on the 30-1 shot Proud Clarion, who was hardly supposed to contend against a quality field that included future Horse of the Year Damascus. But after reserving Proud Clarion back in ninth place, Ussery found that he had a lot more horse under him than he expected.
“I was more or less following Damascus,” Ussery told Kindred in the Courier-Journal. “I didn’t think Damascus would flatten out like he did. But — whoosh! — we went right on by.”
Proud Clarion won by a length while Damascus struggled home third.
The following year, Ussery teamed up in the run for the roses with the Wood Memorial Stakes winner Dancer’s Image, and the results were even more striking as Ussery rated Dancer’s Image last of 14 before boldly urging the colt to advance along the inside.
“I moved with him turning for home. We cut the corner,” Ussery told Kindred while describing the ride that produced a 1 ½-length triumph. “He loved the fence. I did a nice job on him.”
Although Dancer’s Image was subsequently disqualified due to a positive drug test, it took nothing away from the perfection of Ussery’s ride.
As the years went on, Ussery’s momentum started to slow and he rode in fewer races; he eventually retired in 1974 with an official record of 3,611 victories from 20,593 races. At the time Ussery surpassed the 3,000 wins milestone, he was one of only 10 jockeys to have done so. Furthermore, among the current top 200 jockeys by lifetime wins, Ussery’s 17.54% success rate ranks as the 38th best on the chart.
Of course, Ussery wasn’t about to leave the sport completely. He stayed involved as a jockey agent and bloodstock agent, and more than four decades after his retirement from the saddle, Ussery’s name still turns up in the racing news on occasion. He is a regular participant in the annual Jockeys and Jeans Fundraiser to raise money for the Permanently Disabled Jockey Fund, and the 2018 event at Canterbury Park raised a record $310,000.
He never rode a Triple Crown winner, or a legend in the league of Secretariat or Citation, but Ussery did fantastic work with the opportunities he was given. Maybe Seymour Smith said it best when summing up Ussery’s abilities in the Baltimore Sun: “He was often faulted for his seat on a horse. He rode too high, some said, but Ussery had his own style and you cannot argue with the record book.”
In the end, Ussery made such a habit of winning that he couldn’t help but secure a well-deserved spot in the Hall of Fame.
- Ussery’s son, Bobby Allen Ussery, also became a jockey and rode 217 winners between 1978 and 1981.
- The disqualification of Dancer’s Image aside, Ussery is one of just seven jockeys to have crossed the finish line first in back-to-back editions of the Kentucky Derby.
- Although he was not in the saddle for their most memorable triumphs, Ussery did ride and win races aboard the champions Gallant Man, Intentionally, Bold Lad, Cicada, Queen Empress, Vitriolic, and Autobiography.