The 10 best Kentucky Derby winners of all time

April 29th, 2024

Horse racing is often called a game of opinions. That’s true not only about upcoming races, with the fun challenge of trying to solve the puzzle and select the winner. Differences of opinion extend across time when fans reminisce about past champions, and debate their relative merits.

A case in point is highlighting the best Kentucky Derby (G1) winners of all time, distilling a list of 148 horses down to a quintessential 10. Once you get past the handful of non-negotiables, the obvious ones that demand inclusion, it gets awfully tricky – and subjective.

The greats didn’t just run the race of their lives as three-year-olds on the first Saturday in May. They built resumes, often as older horses, that stand the test of time.

With that preamble, here’s my idea of the top 10 horses to win the Kentucky Derby.

1. Secretariat (1973)

Secretariat on the cover of Time magazine

By conquering the Triple Crown in record-setting fashion, Secretariat transcended racing and became a popular icon. He captured the Kentucky Derby while setting the 1 1/4-mile track record of 1:59 2/5 at Churchill Downs, made a monster move to add the Preakness (G1) in track-record time at Pimlico, and passed into the realm of legend in the Belmont (G1). His 31-length rout in the third jewel was not only a stakes-record margin of victory, but he blazed 1 1/2 miles in a record-obliterating 2:24. Secretariat ended his career with a pair of sensational wins on the turf, making him the champion grass horse as well.

2. Spectacular Bid (1979)

Perhaps the greatest horse to win the Derby and Preakness and fall short of a Triple Crown, Spectacular Bid had won 12 in a row before his upset loss in the Belmont. Over the course of his career, the dazzling gray set records from sprints up to 1 1/4 miles, and he successfully carried weights as high as 132 pounds. Spectacular Bid compiled a perfect 9-for-9 campaign as a four-year-old, retiring with a mark of 26 wins from 30 starts.

3. Citation (1948)

Often bracketed with Secretariat and the immortal Man o’ War (who didn’t run in the Derby) as one of the top three in U.S. racing history, Citation rolled through the 1948 Triple Crown while going an incredible 19-for-20 in his three-year-old season. Returning in 1950 after missing a year due to injury, he lost more than he won as an older horse. But Citation regained championship form at the age of six and became the first horse to amass more than $1 million in earnings.

4. Swaps (1955)

The California-bred Swaps famously toppled East Coast favorite Nashua in the Derby, then went back home instead of pursuing the Triple Crown. Not at his best physically when Nashua beat him in their match race, Swaps cemented his legacy at four with a flurry of world records from a flat mile up to 1 5/8 miles, while packing 130 pounds.

5. Count Fleet (1943)

Count Fleet ran away with the Triple Crown, and his 25-length romp in the Belmont was the largest in that classic’s history until Secretariat. Unfortunately, he sustained an injury in his stakes-record performance and never raced again, leaving a nagging what-might-have-been. Count Fleet wired all three jewels by increasing margins and boasted a 10-race winning streak when his career prematurely ended.

6. Seattle Slew (1977)

The first to sweep the Triple Crown unbeaten, Seattle Slew might be considered a bit unlucky to have lost three times afterward, in extenuating circumstances. Yet in fact, he enhanced his historic stature by racing on at four, even with a couple of defeats along with his sparkling wins. “Slew” sped to victory under as much as 134 pounds, and he was too fast for the younger Affirmed in an historic clash of Triple Crown winners in the Marlboro Cup H. (G1).

7. Affirmed (1978)

Affirmed is forever entwined in Triple Crown lore with Alydar, his archrival from their juvenile days, who pushed him to the limit to complete the sweep. Through his superior four-year-old campaign, Affirmed ultimately established greater separation from Alydar in the annals of racing history. He won his last seven races, including a track-record Santa Anita H. (G1), a characteristically gutsy Hollywood Gold Cup (G1) under 132 pounds, and a score over the younger Spectacular Bid in the Jockey Club Gold Cup (G1).

8. Hindoo (1881)

Although comparing champions of different eras is difficult, especially when reaching back into the 19th century, Hindoo compiled a staggering record. He went on an 18-race winning spree at three. Wheeling back six days after the Derby to beat elders in the Clark S., he also scored in the Travers. Hindoo ultimately retired with 30 wins from 35 starts, never finishing worse than third. So dominant was he that sometimes wagering on him was restricted or not even allowed!

9. Whirlaway (1941)

Celebrated for his blistering rallies from off the pace, Whirlaway crushed the Kentucky Derby by a record-tying margin of eight lengths, in then-record time, on the way to Triple Crown glory. The mercurial colt also had a lot of quirks, but he was a warrior throughout his lengthy career. Still the only Triple Crown winner to take the Travers, Whirlaway kept collecting major prizes at four. All told, “Mr. Longtail” won 32 races and placed 24 times from 60 starts. Of those top-three finishes, a grand total of 40 came in stakes.

10. Exterminator (1918)

For high-class longevity, the great gelding Exterminator sets the standard with 50 wins from 100 starts through the age of nine. Nicknamed “Old Bones” because of his lanky, spare frame, he was purchased just as a workmate, but ended up becoming a surprise package. Exterminator upset the Derby at 29-1 in his sophomore debut, then went on to display remarkable distance and weight-carrying capacity. Lumping imposts as high as 138 pounds to victory, he scored major wins at up to 2 1/4 miles.

Now it’s your turn!

If your favorites didn’t make the cut, why not play with the alternatives, and create your own list of the all-time best Kentucky Derby winners?

In the meantime, vote for your preference in our poll!