Who Are The Most Notable Kentucky Derby Winners?

There’s a reason the Kentucky Derby is referred to as “The Greatest Two Minutes In Sports.” Each winner joins the storied and immortal ranks of horse racing’s elite, another chapter in the grand tome of racing history. 

Some, however, have that extra spark that makes their Derby that much more memorable. Let’s take a look back at a few of them.

Remember, the event is happening again this year on May 7, and you can track the 2022 Kentucky Derby TV coverage by TwinSpires here.

Aristides (1875)

Many fine horses were entered in the inaugural Derby, but it was H.P. McGrath, a major breeder and gambler, who brought perhaps the most highly anticipated entrant: Chesapeake, a very talented son of leading sire Lexington. 

To ensure a fast pace for Chesapeake, he also entered Aristides, who was known to have early speed. In the end, Chesapeake never really fired and Aristides, his less regarded stablemate, won by two lengths.

Regret (1915)

By 1915, many fillies had run against the boys in the Triple Crown races. Two each had won the Preakness (Florcaline in 1902, Whimsical in 1906) and the Belmont Stakes (Ruthless in 1867, Tanya in 1905), but none had yet proven best in the Derby. 

That all changed when Regret, widely considered the best two-year-old of any sex in 1914, streaked to victory, remaining undefeated.

Brokers Tip (1933)

This Derby victory provided one of the most famous photographs in sports history. The “Fighting Finish” depicts not only the horses, Brokers Tip and Head Play, battling it out down the stretch, but jockeys Fon Meade and Herb Fischer attacking each other atop their mounts. 

Although both jockeys faced repercussions afterward, Brokers Tip was allowed to remain the official winner. Incidentally, it was the only race he ever won.

Dark Star (1953)

The 1953 Kentucky Derby was notable not so much for who won, but who finished second. Native Dancer, who was the first two-year-old to be named Horse of the Year, was the heavy favorite. 

However, traffic problems throughout the race lead to Native Dancer falling a head short to Dark Star- his only career loss.

Forward Pass (1968)

Medina Spirit’s disqualification from the 2021 Kentucky Derby was not unprecedented. In 1968, a son of a Native Dancer named Dancer’s Image crossed the line first but tested positive for phenylbutazone, a pain reliever that was not permitted as a race day medication in Kentucky at the time. 

Dancer’s Image’s owner, Peter Fuller, fought the decision for four years but was ultimately unsuccessful. Dancer’s Image is also the only horse to have been disqualified from two Triple Crown races, having been taken down from third in the Preakness for interference.

Secretariat (1973)

Some were disillusioned when 1972 Horse of the Year Secretariat finished a lackluster third in the Wood Memorial, his final Kentucky Derby prep. However, the horse fondly referred to as “Big Red” put all doubts to rest on May 5th, 1973. 

He roared down the stretch to an easy win, setting a record of 1:59 ⅖ for the mile and a quarter- one that still stands as the fastest Derby ever, nearly fifty years later.

Unbridled (1990)

Unbridled’s owner, Frances Genter, was 92 years old when she entered her colt in the 1990 Kentucky Derby. She was also almost completely blind and was concerned about being able to see the race. 

Trainer Carl Nafzger provided one of the most touching moments in Derby history by narrating Unbridled’s progress in the race to Mrs. Genter, the emotion spiking as both realized Unbridled was en route to victory. 

Country House (2019)

Maximum Security was the first across the finish line in 2019, but his interference in the far turn caused his disqualification, the first-ever for that type of infraction. 

The winner was declared to be Country House, a 65-1 shot who was wide enough on the turn to avoid traffic.