Oldest jockeys to win Kentucky Derby: How So Happy's Mike Smith can make Churchill Downs history in 2026

Good things come to those who wait. This saying has been seen in action quite recently at Churchill Downs during the Kentucky Derby.

It's no secret that being small and light can help a jockey find more success at the most prestigious horse race in the U.S., but being older with more experience has its own benefits, too. Three of the five oldest jockeys to win the Kentucky Derby have come within the last eight years.

This year, So Happy (15-1 odds) jockey Mike Smith has a chance to become the oldest jockey to win at Churchill Downs. Smith already is the second-oldest jockey to win the race when he was victorious on Triple Crown-winner Justify in 2018. Now, he can pass Bill Shoemaker as the oldest jockey to win a Kentucky Derby.

Here's a look at the oldest jockeys to win The Run for the Roses and where Smith stands with a win on Saturday.

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Who is the oldest jockey to win Kentucky Derby?

Heading into the 2026 Kentucky Derby, 1984 winner Bill Shoemaker is the oldest jockey to win The Run for the Roses. He was 54 years old when he crossed the finish line first on the back of Ferdinand.

Mike Smith became the second-oldest jockey to win at Churchill Downs in 2018. While riding Justify, an eventual Triple Crown winner, Smith was 52 years old. If he were to win this year with So Happy, who has 15-1 odds to win, he would become the oldest jockey to win at age 60.

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Oldest jockeys to win Kentucky Derby

Shoemaker and Smith stand alone as the only two jockeys to win at Churchill Downs aged 50 or older. Now, Smith can stand alone both as the oldest jockey to win and the only one to do so at 60 years old.

Three of the oldest jockeys to cross the finish line first in Kentucky have come within the last eight years. Here are the top five oldest jockeys to win the Kentucky Derby, according to Kentucky Derby data, and a background on each.

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Bill Shoemaker- 54 years old

In 1986, Shoemaker became the oldest jockey to win the Kentucky Derby. This came just one year after Angel Cordero Jr. had broken the record when he was 42 years and 11 months old in 1985. Shoemaker won four Kentucky Derbies in his jockey career (1955, 1959, 1965, and 1986), and he has sole possession of the second-most in race history (Eddie Arcaro and Bill Hartack: five wins).

Mike Smith- 52 years old

En route to jockeying Justify to a Triple Crown set of victories in 2018, Smith began the season by becoming the second-oldest jockey to win a Kentucky Derby. This was the New Mexico native's second derby win (2005- Giacomo). At the 2026 race at Churchill Downs, Smith has a chance to move ahead of Shoemaker as the oldest jockey to win a Kentucky Derby.

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John Velazquez- 48 years old

Velazquez is the second jockey on this list to have a chance of moving up to first place with a win at this year's Kentucky Derby. Along with tying Shoemaker's mark of four Kentucky Derbies won, Velazquez would tie him as the oldest jockey to win at Churchill Downs. His most recent of the three victories came in 2020, when he won with Authentic.

Javier Castellano- 45 years old

Three years ago, Castellano rode Mage to an enthralling victory at Churchill Downs. The Venezuelan now has a chance to tie Velazquez as the third-oldest jockey to win a Kentucky Derby this year with The Puma. This year's race will be Castellano's 18th ride at Churchill Downs.

Calvin Borel- 43 years old

Borel rounds out three of the top 10 spots of the oldest jockeys to win at the Kentucky Derby. His oldest win came in 2010, when he rode Super Saver to victory. Borel also holds spots as the seventh (Mine that Bird, 2009) and tenth-oldest (Street Sense, 2007) jockey to win at Churchill Downs.

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