SHELBYVILLE, Ind. (Wednesday, May 14, 2025) – Despite early morning rain that placed Indiana’s richest turf races on the dirt course, the competition was fierce in the reduced fields for the $150,000 Caesars and the $150,000 Horseshoe Indianapolis, both Black Type races. Smoken Boy was on fire for jockey Emmanuel to score the win in his first start at Horseshoe Indianapolis during Caesars Day.
 
A new acquisition by trainer Cheryl Winebaugh for KEM Stables, Smoken Boy has shown talent over muddy tracks in the past. The race turned in his favor early on during the converted one mile and 70 yard event over the track listed as sloppy. Esquivel put Smoken Boy in the action early from the start to sit right off early leader Brodeur and Jareth Loveberry through the early stages of the race. Esquivel kept the lightly raced sophomore under wraps down the backstretch before moving up to match Brodeur stride for stride in the turn.
 
Once the field hit the stretch, Smoken Boy had a slight advantage over Chasing Liberty and Luis Saez, who slipped up the inside. Three horses were across the track for the early stretch drive before Chasing Liberty and Smoken Boy were in the battle to the wire. The duo almost hit a bird deep in the stretch, that flew by Esquivel’s helmet. But the two horses were caught up in a big battle for the win. Smoken Boy got the edge late in the race to win by a head over Chasing Liberty. Brodeur finished third.
 
“Around the far turn, I was getting after him (Smoken Boy) quite a bit,” noted Esquivel. “He’s still pretty green, and I wanted to keep him engaged in the race. He was going, but he wasn’t going forward. I think blinkers will help him in the future. He is definitely a nice horse.”
 
Smoken Boy was a bit of a surprise for the win, paying $10.20. The striking grey son of Catholic Boy earned his third career win and first on U.S. soil after beginning his career at Hipodromo Camarero Racetrack in Puerto Rico. Winebaugh claimed the horse following his first U.S. start earlier this year at Gulfstream Park. 
 
“This is a bit of a surprise to us today,” said Winebaugh, who is based at Hawthorne Racecourse in Chicago. “He loved the mud in Puerto Rico, so we weren’t too upset when the race came off the turf today. Manny (Esquivel) is an amazing rider and did such a good job with him today. We used Manny when he was an apprentice rider in Chicago, and he won a lot of races for us.”
 
Smoken Boy was initially a $15,000 purchase from the Ocala Breeders and Horses of Racing Age Sale last year at two. He began his career in Puerto Rico last fall with three starts before returning to Florida where he competed in the Grade 1 Florida Derby in his start prior to the Caesar. His career earnings more than doubled with his win Wednesday and he now has more than $162,000 in earnings.
 
“I felt he had a great chance when the race came off the turf,” added Esquivel. “There were some very competitive horses in the race for the turf. But we had a good position early on. Cheryl told me she liked him and was confident he was ready.”
 
The 23^rd season of live Thoroughbred and Quarter Horse racing runs through Thursday, Nov. 13. For more information on racing at Horseshoe Indianapolis, visit www.caesars.com/horseshoe-indianapolis/racing or find details on social media @HSIndyRacing.