Sibling Rivalry: Dylan and Katie Davis Face Off at Saratoga

The “Smiling Assassin” Katie Davis engaged in some friendly fire when she faced off against her brother Dylan in multiple races this weekend at Saratoga.

The two jockeys both grew up near the Saratoga Race Course, where they fell in love with horse racing thanks to their father, Robbie Davis, who was a popular jockey in New York in the 1980s. Robbie rode more than 3,000 winners in his career before transitioning into a trainer. But perhaps his greatest legacy was inspiring his kids to enter the family business.

Aside from Dylan and Katie, the Davis family also includes Jacqueline (aka Jackie, a jockey based in the Finger Lakes) and Edmund (aka Eddie), a rising trainer. All told, that’s four Davis kids on the New York circuit.

“It’s a great support system to have my dad, my sisters, and my brother all actively involved in racing,” Dylan recently told Saratoga Living. “We can all relate to what the others are experiencing. We’re competitive with each other, but first and foremost we’re family and we’re always rooting for each other to have success. Sometimes we’re working together, sometimes we’re trying to beat each other. It’s a fun dynamic.”

“My family, we’re all jockeys, but I’m the best,” Katie said (jokingly) in an episode of the Netflix docuseries Race for the Crown.

Katie’s first opportunity to prove she was right came in the third race at Saratoga on Aug. 14. Katie was aboard Extraordinary One, who was trained by her brother Eddie and entered the race at 17-1 odds. It was the horse’s first turf sprint. Dylan rode the 9-2 Leading Role, who was coming off a second-place finish at Churchill Downs on June 22.

Katie was at the back of the field at the start of the race, with Dylan wedged in between the frontrunners. As they rounded into the stretch, Katie was on the outside, at one point reaching fourth place. But In the Dark proved too much for the Extraordinary One to handle, and Katie ultimately finished fifth. In sixth, however, was her brother Dylan on Leading Role, who fell many lengths behind in the stretch. Score: Katie 1, Dylan 0. 

The siblings had been scheduled to hold a rematch later that day, with Katie atop Solo Dancing and Dylan piloting Wind Dancer (one might be tempted to call the race a “dance off”). Sadly, Wind Dancer scratched, thwarting a Davis v. Davis rematch. Katie solo danced her way to a sixth-place finish in the contest. The score would have to remain Katie 1, Dylan 0 until the following day.

On Aug. 15, the Davises suited up for the seventh race of the day, with Queen Katie riding the long shot Royal Event and Dylan steering the favorite, 2-1 Golden Irish. The oddsmakers were (almost) right on the money, with Irish finishing second, far ahead of Royal who ended at the back of the pack. Score: Katie 1, Dylan 1.

With the friendly family squabble tied at one win apiece, Katie and Dylan entered the final race of Aug. 16 with an opportunity to settle the score. Katie’s ride, the 9-2 Courtly Banker, squared off against Dylan’s 9-2 Pay the Juice. With all things even, who would prevail?

Courtly Banker quickly worked into the thick of the leader pack while Juice lagged behind. Coming into the stretch, Banker took the lead with one furlong to go. Spoken Bluntly made a noble effort to catch up, but to no avail. Katie not only beat her brother but won the race, her first victory of the 2025 Saratoga summer meet. The score: Katie 2, Dylan 1. An emotional Katie entered the winner’s circle to a hearty applause from the crowd, who seemed thoroughly behind the homegrown hero.

Perhaps when Katie declared herself the best of the Davis jockeys, she wasn’t joking after all.