10 little-discussed Kentucky Derby records

Certain Kentucky Derby records have become established as universal racing trivia. Who ran the fastest Kentucky Derby? Secretariat, who clocked 1:59 2/5 in 1973. Which Derby winner triggered the highest $2 win payoff? Donerail, a 91-1 shot who returned $184.90 in 1913.

But every Kentucky Derby record has its converse. The slowest winning time… the lowest win payoff… the smallest winning margin, the least expensive Derby winner….

Boost your Kentucky Derby trivia skills by reviewing these 10 little-discussed records:

Least expensive Derby winner

The $4 million yearling purchase Fusaichi Pegasus is the most expensive Kentucky Derby winner ever sold at auction, but which winner brought the lowest price? Since 1960 the record belongs to Canonero II, the Venezuelan star who sold for just $1,200 as a yearling. That’s less than $9,000 when adjusted for inflation.

Longest documented layoff

Nowadays Derby winners campaign steadily leading up to the Run for the Roses, to the extent that a six-week break leading up to the Derby is considered unorthodox. This hasn’t always been the case—in 1915, the filly Regret won the Kentucky Derby in her 3-year-old debut, returning from a 259-day break to win easily by two lengths.

Lowest win payoff

Everyone remembers Donerail’s massive upset, but which Derby winner produced the lowest winning pari-mutuel payoff? This honor is held jointly by Triple Crown champions Count Fleet (1943) and Citation (1948), 2-5 favorites who returned $2.80.

Narrowest winning margin

Triple Crown winners Whirlaway and Assault famously won the Kentucky Derby by the record-equaling margin of eight lengths, but not every Derby winner is able to score a dominant victory. Eight renewals of the Run for the Roses have been decided by a nose, with Spokane (1889), Azra (1892), Ben Brush (1896), Plaudit (1898), Alan-a-Dale (1902), Brokers Tip (1933), Iron Liege (1957), Tomy Lee (1959), and Grindstone (1996) prevailing by the smallest margin in racing.

Roughest winning trip

They say you need a perfect trip to win the Kentucky Derby, but superior horses have proven this to be false. Few will deny that 1987 Kentucky Derby winner Alysheba received the roughest winning trip in the history of the race. A future Horse of the Year and Hall of Famer, Alysheba clipped heels at the top of the stretch and nearly fell, losing all his momentum in the process. Alysheba could have given up, but instead he shrugged off the incident and re-rallied to win.

Slowest winning pace

Setting slow fractions can help front runners stretch their speed over long distances, as His Eminence demonstrated in the 1901 Kentucky Derby. After running the opening quarter-mile in :25.50—tied for the slowest split ever recorded by a pacesetting Derby winner—His Eminence continued to waltz along through pedestrian fractions of :51, 1:16.25, and 1:43 before kicking home to win in 2:07.75. Manuel, the 1899 Kentucky Derby winner, also warrants a mention. While he didn’t lead all the way, Manuel was in front through a half-mile in :51.25 and 6 furlongs in 1:17.75 (both records) before coming home on top in 2:12.

Slowest winning time

The Kentucky Derby was shortened from 1 1/2 miles to 1 1/4 miles in 1896, and since then the slowest winning time has come courtesy of Stone Street. Racing over a heavy track not conducive to quick times, the unheralded 23-1 shot required 2:15 1/5 to win the 1908 Kentucky Derby by three lengths.

Smallest field

23 horses famously faced the starter for the 100th Kentucky Derby in 1974, exceeding by 20 horses the tiny fields that turned out in 1892 and 1905. But even a three-horse battle can be exciting, as Azra demonstrated when beating Huron by a nose in 1892.

Smallest purse

When Country House won the 2019 Kentucky Derby via disqualification, he collected a record-breaking $1.86 million from the $3 million purse. That’s 652.6 times more than the $2,850 awarded to Aristides for his triumph in the inaugural 1875 Kentucky Derby, which carried a total purse of just $3,050. Runner-up Volcano received $200.

Worst future wager payoff

Future wagers offer the potential to secure high odds on up-and-coming Derby contenders long before the great race is run, but best-laid plans don’t always unfold as expected. When Monarchos upset the 2001 Kentucky Derby at 10-1, he returned $23 to win… significantly higher than the $13 received by bettors who backed Monarchos at 5-1 in Kentucky Derby Future Wager Pool 3, the lowest payoff ever triggered by an individual horse in Pool 3.