Will Take It Noses Out Woodcourt in Fifth Season Stakes

Will Take It rallied up the inside to edge Woodcourt by a head in the one-mile Fifth Season Stakes at Oaklawn Park, covering the distance in 1:38.13 on a fast track and earning a $90,000 winner's share. The 5-year-old Tapit colt, the winner for Willis Horton Racing and listed variously as racing for Whisper Hill Farm, improved to six wins in 22 starts and paid $11.80 to win.

Sunny skies greeted patrons as Oaklawn resumed its postponed classic meet, with a melting mound of snow still in the parking lot serving as a reminder of the winter storm that interrupted racing last week. The Fifth Season was a short field after four defections left five starters, and the race developed into a pace duel that set up Will Take It’s rail rally.

Woodcourt set the pace under pressure from Speed King, carving fractions of :24.08, :47.77 and 1:11.79 through six furlongs. Will Take It sat third along the rail about 1½ lengths off the leaders and appeared blocked until exiting the second turn. Ricardo Santana Jr. found a narrow seam at the head of the lane, squeezed through into the stretch and engaged Woodcourt in a head-bobbing duel, with the pair trading bumps as they raced to the wire. The last eighth was run in 13.04 seconds, producing the fast-rated final time of 1:38.13.

Following the race, the rider of Woodcourt claimed foul against Will Take It, but the stewards did not change the order of finish. Manny Esquivel lodged the objection for interference; the result stood.

Finish order saw Will Take It first, Woodcourt second, American Law third, Speed King fourth and Thoughtthatcounts (spelled Thoughthatcounts in some reports) fifth. Speed King had been installed the 3-5 favorite, while Pony Express, originally listed as the 8-5 program favorite, was among the scratchings along with Seize the Night, Komorebino Omoide and Runaway Again. Nwaonline reported the winner and runner-up carried 122 pounds and listed the win/place/show payouts at $11.80, $5 and $3.60, respectively; the outlet also noted the $90,000 distribution and that a trophy was presented to the connections.

Santana, who rode Will Take It, reflected on the trip: “Many of this horse’s best races is when he’s on the rail. I told Dallas (Stewart) that. He just said: ‘Ride your race.’ That was my plan. He broke a step slow. I got to the rail. He tried to run off. Finally, I got him to relax. From there, he was a different horse. I was able to get through (in the stretch).” Paulickreport and Sports Yahoo reported Santana’s victory marked his 800th Oaklawn win, making him just the fourth jockey in the track’s history to reach that milestone; Nwaonline further noted Santana is an eight-time Oaklawn riding champion.

Trainer Dallas Stewart praised the effort, saying, “He showed up big. This horse has been training terrific, and we're glad to bring him here.” In longer remarks Stewart added, “We've got a very nice horse. It was a great ride today. (Ricardo) Santana showed up big. This horse has been training terrific. We're glad to bring him here and showcase him. It was a terrific race. I think we found out a few things about him. He started off good through the year (2025) and then kind of dropped off a little bit. We got some blinkers on him. I think we learned some things about him. He's a very finicky type horse, but I think we've got him figured out.”

The result provided an early narrative for Oaklawn’s classic meet: a short field, a tactical rail trip, an overturned script for bettors as the chalk was beaten, and a milestone ride for Santana. Connections will weigh the performance and how Will Take It fits into stakes opportunities ahead as Oaklawn’s stakes season unfolds.