Jockey Ricardo Santana Jr. reached a significant career milestone at Oaklawn by guiding Will Take It to a close win in the $150,000 Fifth Season Stakes on Thursday. Santana became only the fourth jockey in Oaklawn history to notch 800 wins as 2026 debutant Will Take It edged past Woodcote by a head in the one-mile race for older horses. Woodcote led most of the way and finished three-quarters of a length ahead of American Law, followed by Speed King and Sort That Count. The field was trimmed to five runners due to injuries affecting favorites such as Pony Express, Komorebino Omoide, Say’s the Night, and Runaway Again.
A protest filed by Woodcote’s jockey, Emmanuel Esquivel, claiming interference during the stretch run was dismissed by officials. The winning time on the fast track clocked in at 1:38.13. Santana executed a ground-saving strategy on Will Take It ($11.80), moving inside Woodcote about 1/16 of a mile from the finish, marking the horse’s second stakes victory. Earlier, Will Take It won the $300,000 Hanshin Stakes at Churchill Downs last June. In his last race of 2025, the 5-year-old Tapit son added blinkers and placed sixth in the 1 1/16-mile Tenacious Stakes at Fairgrounds.
An eight-time Oaklawn riding champion, Santana rode for trainer Dallas Stewart and owners Willis Horton Racing (Kevin Horton) and Whisper Hill Farm (Mandy Pope), who also bred the horse. With this win, Will Take It has six wins in 22 career starts and earnings of $649,919.
The Fifth Season was initially set to begin Jan. 30, alongside Oaklawn’s 51-day major racing calendar, but three days of racing were postponed due to a winter storm that caused a nine-day training shutdown. Oaklawn wrapped up its 13-day holiday meet on January 4.
Racing will resume Friday at 11:30 a.m. CT with 12 races, highlighted by the $1 million Southwest Stakes (G3) and the $300,000 Martha Washington Stakes, both for 3-year-old fillies.
Comments from the connections:
Ricardo Santana Jr. (winning jockey): “This horse runs best on the rail, and that’s what I told Dallas before the race. He told me to ride my own race, so I did just that. The horse started off slower than usual, but once I settled him on the rail, he ran differently. I was able to get through the stretch and finish strong.”
Trainer Dallas Stewart: “We have a very talented horse, and Santana did a fantastic job today. Will Take It has been training well, and I’m glad to showcase him here. He began 2025 strong before slowing down a bit, but I think we learned a lot about him. He can be a bit particular, but I’m confident we’ve figured him out.”
This article was originally published by Paulick Report on February 5, 2026.
Fan Take: Ricardo Santana Jr.’s achievement highlights the enduring talent and competitive spirit at Oaklawn, reinforcing the track’s reputation as a showcase for elite racing. Will Take It’s rising form also promises exciting future contests, keeping fans engaged and optimistic about the sport’s upcoming seasons.
