Horse Racing History: The Biggest Bets Ever Placed

The history of horse racing is filled with stories of bettors and horsemen who gambled big dollars in search of huge payoffs.

A definitive list of the biggest horse racing bets ever placed is difficult to compile due to factors like inflation, currency exchanges, and the fact not every big bet has received high-profile publicity.

Nevertheless, in terms of size, payoff, and/or ambition, the following four gambles certainly rank among the biggest bets ever placed in horse racing history:

J. K. L. Ross wins $50,000 on a losing horse

John Kenneth Leveson “Jack” Ross owned Sir Barton, who in 1919 became the first Triple Crown winner. Ironically, none of Sir Barton’s classic wins earned even half as much money as the $50,000 Ross won on a head-to-head Kentucky Derby bet involving Sir Barton’s losing stablemate, Billy Kelly. Arnold Rothstein, known for his high-stakes gambles, bet Ross $50,000 (about $950,000 in 2024 dollars) that a horse named Eternal would finish ahead of Billy Kelly in the Kentucky Derby. Even though Billy Kelly lost the Derby to Sir Barton, his runner-up finish was sufficient to win Ross the bet.

RELATED: True Crime in Horse Racing: The Notorious Life of Arnold Rothstein

New Jersey bettor wins nearly $3.6 million on Rainbow Pick 6

On Feb. 22, 2013, a New Jersey bettor wagered $3,118.50 on the 10-cent “Rainbow Pick 6” at Gulfstream Park. The bet size wasn’t remarkable, but the payoff was astronomical. After a series of upsets, the New Jersey bettor held the lone winning ticket and cashed a jackpot payoff of $3,591,245.44 (over $4.8 million in 2024 dollars).

Connections of Wild Again pay $360,000 to enter the Breeders’ Cup Classic

With a purse of $3 million, the inaugural Breeders’ Cup Classic (G1) in 1984 was the richest horse race ever held to that point in time. Because Meadowlands Cup (G1) winner Wild Again wasn’t nominated to the Breeders’ Cup early on, owner Black Chip Stable had to pay a $360,000 supplemental nomination fee (over $1 million in 2024 dollars). It was definitely a gamble—Wild Again started as a 31-1 longshot—but in a driving finish, Wild Again prevailed by a head and earned $1.35 million (about $4 million in 2024 dollars).