Gaffalione Adds Kentucky Oaks to Ever-Expanding Resume

2015 Eclipse Award-winning apprentice jockey. 2019 classic winner. Two-time Breeders' Cup winner in 2022. And now, Kentucky Oaks (G1) winner.

Such accomplishments fill the resume of 28-year-old rider Tyler Gaffalione, who, on May 5 before 106,381 fans at Churchill Downs, captured the $1.25 million Kentucky Oaks, North's America's most prestigious race for 3-year-old fillies, aboard Godolphin's Pretty Mischievous .

Deftly tucking his mount in behind horses into the first turn from post 14, Gaffalione allowed the Into Mischief   filly to advance outside toward the frontrunners down the backstretch and into the final turn. Then coming into the lane, it was her time to shine, and with Gaffalione imploring her to finish off her rivals, she withstood a rally from Gambling Girl  to score a diminishing neck victory.

Galloping his mount out past the finish, Gaffalione raised and pumped his right hand in excitement, relishing his first Oaks victory at Churchill Downs, where he is a seven-time leading rider.

"I can't really even put it into words," he said in response to a question about what winning the Oaks means to him. "I'm so happy I was able to accomplish this, especially being at my home track now at Churchill Downs. My family's here today and I couldn't think of anyone to do it better with."

For Gaffalione, the Oaks marked the 18th grade 1 victory in a career that began in just 2014, and is among the most meaningful, with other highlights coming with winning rides on War of Will   in the 2019 Preakness Stakes (G1), Wonder Wheel  in the 2022 Breeders' Cup Juvenile Fillies (G1), and Caravel  in the Breeders' Cup Turf Sprint (G1T).

He teamed with the latter Friday to win the $300,000 Unbridled Sidney Stakes on the Kentucky Oaks undercard. She is scheduled to race next in the prestigious Royal Ascot meeting next month.

"It's a dream come true for me," he said of his Kentucky Oaks success. "I grew up in this business; I idolized these guys I'm running with and competing with."

His father, Steve Gaffalione, is a former jockey, as was his grandfather, Bobby Gaffalione. Tyler, who grew up in South Florida, got his first pony at age 4 and would often follow his father around the barn area as a child. 

He wanted to get his jockey license at age 16, but his father reminded him of the family's rule of finishing high school.

His subsequent education has come in the saddle, with obvious lessons learned. The young jockey is 4-for-5 when teaming with Pretty Mischievous, who can be a tricky filly to ride, owing to her tendency to wait on rivals upon making the lead. Gaffalione's patient handling contributed to her victory Friday, though in the rider's typical humble manner, he credited Walsh's horsemanship and decision to add blinkers to her racing equipment to improve her focus.

"She has a tendency to kind of wait on horses, did the same thing a little bit today, but the addition of blinkers I think helped with that," he said.

Walsh was quick to praise his jockey.

"He did a super job, not just today, but he came in, and he's worked this filly from the very get‑go and came in and worked her three times before she ran today, so that we would get it right," Walsh said. "It's just one of the few occasions where everything came together, and it came right on the big day."