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The Kentucky Derby is back for 2026, bringing all the traditions like mint juleps, bold hats, and high-stakes betting. For many viewers, it's also a chance to make extra money on the side. This year, the race happens on Saturday, May 2, at Churchill Downs in Louisville, Kentucky.
Every year, hopeful bettors place small wagers dreaming of a big payday, and sometimes, those bets actually hit. Over the years, certain Derby winners have delivered massive payouts, turning modest bets into surprising wins.
Here are 10 of the most famous Kentucky Derby champions and how much money they earned—plus what their victories could have meant for bettors looking to make a little extra cash on the side.
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Whirlaway (1941)
In 1941, Whirlaway became the fifth Triple Crown winner, picking up wins at the Kentucky Derby, Preakness Stakes, and Belmont Stakes. He was one of only four horses to win the Derby by eight horse lengths, the biggest margin of victory in the race's history. Whirlaway ended his career with $561,161 in earnings and a record of 32-15-9.
Genuine Risk (1980)
Genuine Risk is one of only three fillies to win the Kentucky Derby. She also came in second place in the Preakness Stakes and Belmont Stakes that followed, becoming only the second filly to complete all three races. After she retired from horse racing, she sired Triple Crown winner Affirmed. Genuine Risk ended her career with $646,587 in earnings.
Spectacular Bid (1979)
Spectacular Bid had plenty of speed when he won the Kentucky Derby and Preakness Stakes in 1979 before an injury caused him to place third at Belmont. But he still broke several track records and holds the record for the fastest 10 furlongs on dirt. Spectacular Bid also turned out to be a spectacular moneymaker, with $2,781,608 in lifetime earnings and a record of 26-2-1.
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Citation (1948)
Citation was a notable Triple Crown winner who also had a run of 16 consecutive wins during his career. His earnings from the Kentucky Derby, as well as other major wins in his career, pushed him above the million-dollar mark, making him the first horse to earn that much. He retired with $1,085,760 in earnings.
War Admiral (1937)
War Admiral's run in 1937 was the first of the three wins he picked up to win the Triple Crown that year. But he's also known for being a competitor to Seabiscuit, who beat War Admiral in a special two-horse race showdown in 1938. Both were immortalized in the book "Seabiscuit" and the movie of the same name in 2003. War Admiral won $273,240 with 21 wins over the 26 starts of his career.
Affirmed (1978)
Affirmed became a Triple Crown winner in 1978 after winning the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes. He also won several other prestigious races that year, including the Santa Anita Derby and Hollywood Derby.
Affirmed was the last Triple Crown winner in the 1970s and the last before a 37-year drought that didn't end until 2015. Affirmed finished off his racing career with a whopping $2,393,818 in earnings.
Seattle Slew (1977)
Seattle Slew was one of three horses to win the Triple Crown in the 1970s and one of only two horses to win the Triple Crown after being undefeated in every race they had entered going into the Kentucky Derby. Seattle Slew earned $1,208,726 during his career with a record of 14-2-0.
American Pharoah (2015)
American Pharoah broke a 37-year drought to win the Triple Crown by winning at the Kentucky Derby before stellar showings at the Preakness and Belmont. The horse also won the Breeders' Cup Classic, becoming only the second winner of the Grand Slam of Thoroughbred racing after 1941 Grand Slam winner Whirlaway. American Pharoah retired with racing earnings of $8,650,300.
Smarty Jones (2004)
Smarty Jones picked up a win at the Kentucky Derby and Preakness Stakes in 2004 before coming in second at the Belmont Stakes and missing out on the Triple Crown. The horse still holds the record for the biggest margin of victory in the Preakness Stakes. Smarty Jones ended his racing career with $7,613,155 in earnings.
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Secretariat (1973)
Secretariat had a convincing win at the Kentucky Derby in 1973, setting the fastest time with a win under two minutes. It's a record that still holds today. The thoroughbred also set track records at the Preakness Stakes and Belmont Stakes on his way to the Triple Crown that are still held to this day. In his career, Secretariat won a total of $1,316,808 in earnings.
Bottom line
The Kentucky Derby may be known for its pageantry, but it's also a massive money event, with a record $5 million purse in recent races and millions going to the winning team alone.
Still, while it can be tempting to try to get ahead financially with a well-placed bet, the odds are always uncertain. For most people, consistent strategies, like saving or investing, are far more reliable ways to build wealth over time than chasing a one-day payday at the track.
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