The 5 Best Kentucky Derby Races Ever. I mean EVER!

Written By Darren Cooper on May 4, 2022 - Last Updated on May 5, 2022
Kentucky Derby best races of all time

The Kentucky Derby has enthralled the sports world since its first running in 1875. The horse racing industry is filled with colorful characters, colorful horses, whimsical names and legends.

Saturday is the 148th edition of the “Run for the Roses” at Churchill Downs in Louisville. There will be fancy hats, mint juleps to drink and a horse race to bet on, win, place or show.

When you’ve been holding something for over a century, there are bound to be some amazing moments (and some lowlights too). These are the best five Kentucky Derby races ever:

No. 1, 1978: A rivalry for all time

We can endlessly debate the greatest horse of all time, and the greatest Kentucky Derby champion, but there has never been a rivalry in the Triple Crown like Affirmed and Alydar.

The world became aware of the competition between the two thoroughbreds at the 1978 Kentucky Derby. Alydar was a 6-5 favorite at post-time.

Affirmed was being ridden by 18-year-old wonder kid Steve Cauthen.

This was the first of three amazing Triple Crown races between the two. Sensitive Prince had the early lead, but Affirmed made a big move on the backstretch to the front. As Affirmed neared the finish, Alydar shot up behind him into second.

Incredibly, the same scenario would play out in both the Preakness and Belmont that year with Affirmed winning all three races. 

All told, in the 10 races between the two horses, Affirmed would win seven, Alydar three. Cauthen is still the youngest jockey to win the Triple Crown. 

No. 2, 1996: One last run

You watch the 1996 Kentucky Derby and you ask yourself the question everyone else did at the time. Where did he come from?

Grindstone was 15th early, as Honor and Glory took the lead. The favorite, Unbridles Song, was third and then got to the front and drew clear of the field.

Grindstone, the son of Unbridled who won the Derby in 1990, had won the Louisiana Derby and had been second in the Arkansas Derby. The D. Wayne Lucas-trained horse was unspectacular and had been a non-factor in the race stuck in traffic.

Until they made the final turn.

Grindstone was fifth and far from the rail as Cavonnier rolled to the front. Grindstone surged to the front and edged Cavonnier by a nose at the wire. It’s arguably one of the greatest runs a horse ever navigated at Churchill Downs.

Just days later, Grindstone was retired from racing with a bone chip in his knee, so his charge on that Saturday in May is a lasting image of him. He would sire Belmont winner Birdstone. Grindstone died at age 29 in March of 2022.

No. 3, 1964: Dancing through it all

The 90th Kentucky Derby became a two-horse showdown between Northern Dancer and Hill Rise. Hill Rise, ridden by Bill Shoemaker, had won eight straight when he entered the starting gate. 

Both horses were in the back of the pack early, but Northern Dancer jumped in front and was two lengths ahead at the top of the stretch.

Hill Rise made his charge. Northern Dancer jockey Bill Hartack switched to a left-handed whip to spur Northern Dancer to the finish and won by a neck. Northern Dancer was the first Canadian-bred horse to win the Derby.

He finished in a then-track record of 2-flat.

No. 4, 1957: Stands the test of time

The nine-horse field for the Kentucky Derby in 1957 might be the best of all time. It included three future Hall of Fame horses:

  • Gallant Man
  • Round Table
  • Bold Ruler (Secretariat’s Dad)

None were the morning line favorite. That was Gen. Duke, but he was scratched with a bruised foot.

Gen. Duke’s stablemate Iron Liege was under the guide of famed jockey Bill Hartack. He chased down Gallant Man down the stretch. It was the closest finish in the Derby since 1933.

What people remember about this race though is Gallant Man’s jockey Bill Shoemaker briefly rising in the stirrups with his horse in the lead. Shoemaker mistook the 16th pole for the wire. Did his bobble cost Gallant Man the victory? We will never know. 

No. 5, 1933: The fighting finish

This is one of those stories that if it happened today Twitter would melt down and there would be a congressional investigation. It’s called the “Fighting Finish.” 

Jockey Don Meade was on Brokers Tip. Herb Fisher was on Head Play.

How crazy was this race? Head Play balked at entering the starting gate so was allowed to begin the race outside.

On a muddy track, Brokers Tip and Head Play got clear of the field. They were neck-and-neck on the stretch. Then both jockeys began to wrestle.

The two men were so close that they grabbed each other’s saddlecloths, bridles, and legs. They whipped the other horse. In the video of the race, you can see Fisher swat his whip at Meade just past the finish.

A famous picture taken by the Courier-Journal shows the two jockeys clawing at each other, their horses churning to the finish. Brokers Tip won by a nose. It was the only race he ever won.

Both jockeys carried the fight into the locker room and were suspended for 30 days.

Photo by Al Behrman/Associated Press
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Darren Cooper

Darren Cooper was born and raised in Southern Louisiana, just a short pirogue ride away from New Orleans. He started his journalism career at the New Orleans Times-Picayune and has been a writer and columnist in New Jersey since 1998. He's won 14 statewide press awards and earned his first Associated Press Sports Editors Top 10 award in 2022.

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