Horse Racing’s Most Valuable Triple Crown Winners of All Time

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The world is fascinated with the Triple Crown leading up to the June 7th Belmont Stakes in which Kentucky Derby and Preakness winner California Chrome will race for the chance to win the first Triple Crown in 36 years. The anticipation has horse racing fans everywhere excited and nervous, hoping everyone’s new favorite horse can do it. However, that leads people to wonder, which horses are the most valuable Triple Crown winners in history if you calculate their earnings based on inflation.

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Whirlaway, 1941

He was the first horse in history to earn more than a half million dollars in his career. After retiring, however, the horse only had 32 wins of 60 starts. He was never expected to win the Triple Crown due to his difficult nature. It was said he was difficult to ride, and his jockey was specially chosen for him because he was thought to be the only one capable of handling the horse. His half million dollars today would equal more than $9 million, making him the most valuable Triple Crown winner in the history of horse racing.

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Affirmed, 1978

After retiring from his racing career Affirmed was worth more than $2,393,818 million, which made him the first horse in race history to ever earn more than $2 million. His career ended with 22 of 26 wins, which is very impressive for a horse that ran until he was 3. He won the 104th Kentucky Derby and went onto win the Triple Crown after racing his arch rival 10 times, winning 7 of those races against Alydar. Today, his earnings would be worth more than $8.7 million.

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Assault, 1946

Assault sustained a serious injury that caused one of his right legs to become crooked, something that should have ended his career – but didn’t. This Texas-bred horse only won two races by the time he was 2, though he turned that around to win 8 of 15 by the time he was 3. He retired at 7, which is very old in horse racing years, with a total of only 18 of 42 wins. Today, he’d be worth $8.2 million, making him the third most valuable Triple Crown winner in history.

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Seattle Slew, 1977

Seattle Slew’s win was something of a scary tale for the world, but no one more so than his owner and trainers. When he raced the Kentucky Derby in 1977, Seattle Slew was the 1-2 favorite, but looked as if he’d lose the race after falling down at the break and losing almost 6 lengths. His jockey, Jean Cruguet, however, got the horse back on his feet and managed to take the victory, leading him on two more races to take home the Triple Crown. He raced for four years, even after becoming ill and nearly dying. He even beat the following year’s Triple Crown Winner in the Marlboro Cup prior to his retirement. Today, Seattle Slew would be worth $4.7 million.

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Gallant Fox, 1930

With a 2 for 7 record at 2, he wasn’t the horse anyone expected to win it all, or even do very well to start with. However, Gallant Fox went on to win the Triple Crown in 1930 with jockey Earl Sande. The horse retired once he turned three with a record of 11 of 17 wins. He’s also famous for siring another Triple Crown horse to sire another Triple Crown winner. Today, his earnings would equate to more than $4.65 million.

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War Admiral, 1937

Back in the 1930s, it seemed horses won the Triple Crown more often than not, making 1937’s winner the third winner in 7 years. The son of horse legend Man o’War, War Admiral had a career to be proud of. This small brown colt won 8 of 8 races in three years. He retired in his fifth year after winning 21 of 26, losing famously to Seabiscuit at Pimlico. His lifetime earnings would equal $4.5 million today.

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Omaha, 1935

Omaha was sired by Triple Crown Winner Gallant Fox. Though he only won 9 of his 22 career starts, he made the Triple Crown a family affair for his owner and trainer, Belair Stud and Sunny Jim Fitzsimmons after they won previously with Gallant Fox. The only difference between his win and Gallant Fox’s win is that Omaha was ridden by a different jockey, Willie Sanders. Today his earnings would equal $2.67 million.

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Sir Barton, 1919

Sir Barton is your typical Cinderella story – in horse terms. He was purchased for a mere $10,000 and was 0 for 6 as a two-year-old. His purpose was to pace another horse with no hope of winning. However, with the help of John Loftus, his jockey, Sir Barton won all three races and ended up being the first ever Triple Crown Winner. Today, the horse’s winnings would equate to $1.6 million.

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Written by Tiffany Raiford

Tiffany Raiford is a lifelong Floridian, wife to my high school sweetheart and mother of four littles (two girls and boy/girl twins...no, they are not identical and yes, I'm sure). My kids love to whine, so I love to wine. My loves include nap time, bed time, date night, travel and evenings and weekends when my husband is home because he handles all diaper changes.