5 of the greatest Kentucky Derby story lines of all time

In its 150 years of history, the Kentucky Derby has produced an endless array of memorable moments. Here’s a look at five of the greatest story lines of all time. 

Longest odds

With odds of 91-1, Donerail is the highest-price winner in the history of the race. The 1913 winner rallied from fifth at the top of the stretch to win by a half-length. Read all about the record holder here. Rich Strike, the 80-1 upset winner in 2022, is the closest to rival these odds.

Largest win margin

Four horses have won the classic by eight lengths. One year after Donerail’s longshot victory, Old Rosebud helped the sensational rise of the Derby with this daylight score, the gelding’s eleventh consecutive win. Johnstown matched the distance in 1939, defeating eventual Horse of the Year Challedon. Whirlaway (1941) and Assault (1946) tied the record en route to becoming Triple Crown winners. 

Winning fillies

Three fillies have worn the roses. The year after Old Rosebud stunned the Derby crowd, Regret became the first filly to win the race in 1915. She was victorious in all of her races as a two-year-old and three-year-old, beating males every time. The second female winner, Genuine Risk, was purchased by Bert and Diana Firestone after their 14-year-old son selected her at a sale. The chestnut filly won in 1980 at 13-1 odds. In 1988, the filly Winning Colors gave Hall of Fame trainer D. Wayne Lukas his first of four Derby wins. This year, he saddles Just Steel. 

Fastest derby

The great Secretariat holds the record for fastest Derby, attained in 1973. The bright red chestnut was the first to run it in under two minutes. One other horse has accomplished this feat since then—Monarchos in 2001—but he didn’t break Secretariat’s record. 

Smallest win margin

Eight horses have won by a nose: Spokane (1889), Azra (1892), Ben Brush (1896), Plaudit (1898), Alan-A-Dale (1902), Iron Liege (1957), Tomy Lee (1959) and Grindstone (1996). Grindstone gave Lukas his third Derby win. The colt was unable to compete after the Derby due to a bone chip in his right knee. He continued to be a success in breeding. One of his best known offspring is Birdstone, who denied Smarty Jones’s Triple Crown bid in 2004, beating the colt by a length in the Belmont S. 

For more Kentucky Derby records, trivia, and information, see this factbook.