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Mike Smith Rides So Happy at 60, Chasing Kentucky Derby History

A win Saturday at Churchill Downs would make Smith, already the second-oldest Derby winner, the oldest jockey ever to win the race.

Churchill Downs Pano 
May 2017
Louisville, Kentucky

2017 Kentucky Derby.
Churchill Downs Pano May 2017 Louisville, Kentuc…      Churchill Downs Kentucky Derby    squirrel83 from Astoria, NY , USA / Wikimedia Commons (CC BY 2.0)
By Free News Press Editorial Team
Published May 2, 2026 at 7:47 AM PDT

At 60 years old, jockey Mike Smith arrives at Churchill Downs on Saturday with a legitimate shot at becoming the oldest jockey in Kentucky Derby history.

Smith is riding So Happy, listed at 15-1 odds, in the 2026 Run for the Roses. He already holds the distinction of being the second-oldest jockey to win the Derby, having guided Justify to victory in 2018 at age 52. That ride was the start of a Triple Crown sweep. A win Saturday would push him past Bill Shoemaker, who was 54 when he won aboard Ferdinand in 1986, and give Smith a record he would hold alone.

Shoemaker's 1986 win came just one year after Angel Cordero Jr. had set the previous age record at 42 years and 11 months. Shoemaker won four Kentucky Derbies total, placing him second all-time behind Eddie Arcaro and Bill Hartack, who each won five.

Smith's 2018 victory was his second Derby win. If So Happy crosses the finish line first, it would be his third.

The Sporting News noted that three of the five oldest jockeys to win the Derby have done so within the last eight years, a stretch that has reframed assumptions about age and performance at Churchill Downs. Experience, it turns out, carries weight in a race where composure and positioning in a 20-horse field can determine everything.

The Derby goes to post Saturday afternoon.

Postcard view of the stands at Churchill Downs.
Postcard view of the stands at Churchill Downs.      Churchill Downs Kentucky Derby    Unknown authorUnknown author / Wikimedia Commons (Public domain)