Hemmed in behind horses at the top of the lane, Expected Ruler did not appear a likely winner of the fifth race last Friday at Keeneland. Carrying odds of 16-1, jockey Didiel Osorio managed to improvise, bulling through traffic to get the 3-year-old colt racing room. The pair surged forward to win by three-quarters of a length in the 5 ½-furlong turf event, just a tenth of a second off the track record.
It's a story of close friends, and of families that brought together two boys barely out of their teens to capture their first victory at Keeneland. Born into the racing industry, 20-year-old trainer Liam Benson and 21-year-old Jose Santos Jr., the agent representing Osorio, both know the value of hard work, most recently learning to balance their racing careers with college studies.
“It's really cool to win a race like that with one of your best friends,” said Santos. “We had 15 of our friend group out there at Keeneland. Some of them had never even been to a horse race. It was just an insane experience for a lot of people.”
For Benson, the journey began when his parents moved to Florida and purchased Mayo West Farm 11 years ago, breeding their own Thoroughbred racehorses. Benson actually helped pull Expected Ruler from his mother and was a major part in the colt's early training on the farm. Last fall, the son of Leroidesanimaux returned the favor in a big way: he captured the listed Tyro Stakes at Monmouth Park in his very first start, giving young Benson his first stakes victory as a trainer.
Santos learned horse racing from a slightly different angle. His father, Jose Santos, is a Hall of Fame jockey who captured the 2003 Kentucky Derby riding Funny Cide. Santos grew up in Florida in the company of top jockeys, playing video games with Hall of Famer Angel Cordero and studying his sister's godfather John Velazquez, also in the Hall of Fame.
Santos and Benson's friendship began when they worked as tour guides for the Kentucky Derby Museum in 2013. Each had come to Kentucky for college but have had their careers take off even before graduation; Benson received his trainer's license at 18 and ran his own barn at Monmouth Park that summer, and Santos became an agent the same year, picking up the talented Osorio, once Panama's top bug boy.
“He's one of my best friends,” said Benson. “We try and help each other out as much as we can.”
That help was particularly timely last week, as Benson's colt shipped to Keeneland six days before the race but the trainer could not find an exercise rider available to gallop him.
“Didiel went and jogged and galloped him Tuesday, Wednesday and Thursday, to get up on him in the morning and to help out Liam,” said Santos. “Liam was going to school too and he had no one to really help him out. It was a nice team effort.”
The horse was a bit wild in the mornings leading up to the race, testing Osorio the entire way around the track.
“They fought for about a mile – it was hilarious,” laughed Santos. “When they got to the top of the stretch, he just kind of let him roll down. When he came back, that's when Didiel said 'we're going to win this race.'”
Benson wasn't feeling quite as confident. After Expected Ruler's winning turf debut, Benson opted to try him on the dirt at Churchill Downs in the Gr. 3 Iroquois. The colt was pressured on the lead early and faded to 11th. Next, he entered Keeneland's Gr. 3 Dixiana Bourbon, where he finished 11th once again, tiring over a muddy track. Back on the turf after a winter break, Expected Ruler again faded, sixth in a listed stakes at Gulfstream.
“I guess I had a weakened sense of confidence about him going into this race,” said Benson. “There was so much pressure – it wasn't from my parents, it wasn't from anyone – I just know we've got this nice horse. He wouldn't have won that stakes first out if he wasn't. He's obviously got a bit of class.”
When Expected Ruler broke free at the sixteenth pole, Benson jumped into the air with joy.
“It was vindication more than anything,” he said. “We finally managed to put everything together. I'm a lot more comfortable going forward because I know what to expect. I don't want to say 'catch lightning in a bottle again,' because horses win stakes all the time, but for me, that's what it was trying to do.”
Benson and Santos will both graduate from the University of Louisville, Benson with an Equine Business degree in December, and Santos in Broadcast Communications isn't far behind. Benson plans to operate as a full-time trainer after graduation and said several owners have taken notice after Expected Ruler's big win. Santos, meanwhile, will continue on his successful path as an agent, which led to Osorio taking down the leading rider title at Ellis Park last summer.
“Even when I'm at Monmouth and he's in Kentucky or Indiana or wherever he's riding, we talk on a regular basis,” said Benson. “We talk about my horses, what he's doing, how Didiel's doing. He's taught me a lot, there's no doubt about that. His dad's a Hall of Fame rider, and I've learned a lot from listening to Jose over the years, like what to look for in a rider. I've got nothing but respect for the kid, he's worked hard all his life.”
“I've learned a lot from Liam as well,” Santos echoed. “For the most part, I only knew the jockey part of it. I didn't really know much about training a horse. I've always been able to handicap and all that, but he's taught me tendencies in horses.”
At the end of the day, it's their strong friendship which made the win with Expected Ruler so unique.
“I've never been that excited,” said Santos. “It's really fun winning for Liam. To win one, and for it to be an allowance race at Keeneland with the horse that definitely means the most to him, it was a real special experience.”
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