Compared with some, the career of jockey Charles “Charley” Kurtsinger didn’t last all that long. Modern-day superstar jockey Mike Smith took out his jockey's license in 1982 and continues to compete at the highest level; Russell Baze, the all-time leading North American jockey by career wins, started out in 1974 and stayed at the top of his game until he retired with 12,842 wins in 2016.

In contrast, Kurtsinger was a jockey for just 15 years, starting his career in 1924 and hanging up his tack in 1939. But oh, what an incredible streak of success he achieved during those 15 years!

Born in 1907, Kurtsinger—nicknamed the “Flying Dutchman”—started riding professionally at the age of 17, and after a few slow years at the start of his career, things really started to pick up in the 1930s. In 1931, Kurtsinger got his first chance to ride in the Kentucky Derby, his mount being a talented colt named Twenty Grand. After a successful campaign in 1930 that had included a win in the Kentucky Jockey Club Stakes, Twenty Grand had won the Wood Memorial and finished second in the Preakness Stakes (then run before the Derby) despite encountering some trouble during the race.

In the Derby, Twenty Grand was favored to win and did so with authority, sweeping from the back of the field to win easily by four lengths. Thus, Kurtsinger had accomplished the fairly remarkable feat of winning the Derby on his very first attempt, a feat achieved by only nine jockeys since then. A month after the Derby, Twenty Grand won the Belmont Stakes by 10 lengths to sweep two-thirds of the Triple Crown; if not for his troubled trip in the Preakness, he might have been a Triple Crown winner.

Twenty Grand would later add wins in the Dwyer Stakes, Travers Stakes, Saratoga Cup, Lawrence Realization, and Jockey Club Gold Cup (the majority of these with Kurtsinger in the saddle) to his record and would be recognized as Horse of the Year. Thanks in great part to Twenty Grand, Kurtsinger was the leading jockey by money won in 1931, with the horses he rode earning an impressive $392,095.

Two years later, Kurtsinger would be back in the Triple Crown spotlight aboard Head Play, who had finished second in the 1933 Kentucky Derby with Herb Fisher in the saddle. That race is renowned to this day as the “fighting finish” Derby, so called because the riders of the top two finishers had grappled and fought with each other down the homestretch. With Fisher suspended for his part in the fight, Kurtsinger picked up the mount on Herb Play for the Preakness and delivered with a four-length victory. Head Play’s overall accomplishments earned him recognition as the champion 3-year-old colt of the year, and after making just one start in 1934, Head Play returned in 1935 to win seven of his 13 starts, including a memorable win over Discovery in the 1935 Suburban Handicap.

Having completed his personal Triple Crown by winning the Preakness with Head Play, the next step for Kurtsinger was to win the Triple Crown with one horse in a single year, and an unimposing brown colt named War Admiral would allow him to achieve that goal.

KURTSINGER WITH WAR ADMIRAL

Courtesy of Keeneland-Morgan

As a 2-year-old in 1936, War Admiral was nothing special, but the following season, he rose to stardom and would prove to be unbeatable. After wins in an allowance race and the Chesapeake Stakes, Kurtsinger guided War Admiral to an easy win in the Kentucky Derby, a narrow triumph in the Preakness, and a three-length romp in the Belmont Stakes despite a stumble at the start. War Admiral and Kurtsinger would pair up for three more wins later that year, and after receiving Horse of the Year honors for 1937, War Admiral came back as good as ever in 1938, winning major stakes races like the Widener and Saratoga Handicaps with Kurtsinger in the saddle.

During the glory years of War Admiral, Kurtsinger also enjoyed success aboard Menow, the champion 2-year-old colt of 1937. After a relatively unremarkable start to his career, Menow showed improvement as the season progressed, winning the Champagne Stakes and Futurity Stakes by four lengths apiece to secure the championship. Thanks to Menow and War Admiral, Kurtsinger was once again the leading jockey in the country by money won, winning $384,292 in purse money.

The following year, Menow ran fourth in the Kentucky Derby and third in the Preakness with other jockeys in the saddle, but rebounded nicely when reunited with Kurtsinger to win the Withers Stakes at Belmont. Menow would retire with a respectable record of seven wins from 17 starts but was unbeaten in four starts with Kurtsinger aboard.

The rollercoaster that was Kurtsinger’s rise to success came to a halt in 1939 when he retired from the saddle, and in 1946, he passed away from pneumonia. But his accomplishments did not go unremembered, and in 1967, he was inducted into the Racing Hall of Fame. He remains one of just 12 jockeys to have won the Triple Crown—that’s pretty good company!

Note: This story was originally published in November 2015 and has been updated.

Fun Facts

• According to statistics on the National Museum of Racing and Hall of Fame website, Kurtsinger rode 721 winners from 5,651 races for a win percentage of nearly 13%.
• War Admiral wasn’t the only Triple Crown winner that Kurtsinger had the privilege to ride—he also rode 1935 Triple Crown winner Omaha in a trio of races in 1934, including a narrow defeat in the Junior Champion Stakes.
• Kurtsinger isn’t the only jockey to have been nicknamed the “Flying Dutchman”—Fred Taral, who won the 1899 Kentucky Derby aboard Manuel, was also known by that title.