It was like choosing the favorite of your two sons, trainer Mark Casse said.
There was War of Will, the Preakness winner and favorite of his two horses in the 151st running of the Belmont Stakes. And then there was Sir Winston, the dark horse in the truest sense: The horse, he said, who last year wasn’t even in his top 15 2-year-olds.
“It is like your son,” he said. “You don’t want to see him [lose]. It’s like having two kids …The Belmont is big to me, huge to win, but it still hurt that War of Will didn’t run better. I’m still a little emotional about that.”
All that notwithstanding, something changed in Casse and he started watching the race, just around the half-mile pole. He saw War of Will start to struggle (he finished ninth) and Casse turned his attention to his horse’s less-flashy sibling, who was doing surprisingly well.
“I looked for Sir Winston and [jockey] Joel [Rosario] ducked inside and, to be honest, I started hollering for Sir Winston at that time,” Casse said. “He’s an amazing little horse. If this time last year, if you had asked me to rate my top 20 2-year-olds, he would be about 16 or 17th.”
But, much like his namesake, Winston Churchill, Sir Winston knows a thing or two about triumphing over long odds. He was a 10-1 underdog at Belmont on Saturday, and it was even a feat to get that far. His first two races, at Churchill Downs and Saratoga, in 2018, were nothing short of disappointing, finishing second to last both times, and by large margins. But Casse said he saw a reason not to give up on Sir Winston, and conveyed as much to owner Tracy Farmer.
“Mr. Farmer,” Casse recalled saying, “don’t give up on him. It’s crazy, but I see something. Let’s give him some time to develop, because he would finish.”
So Sir Winston raced at Woodbine three times, winning twice, and eventually found himself here at Belmont, where he came in second at the Peter Pan Stakes, with a long, winding road in between.
“I’m proud of him because he’s what our operation represents,” Casse said of Sir Winston, who is homebred. “I feel like we develop horses.”
And really, though it always seemed that War of Will would be his ticket in this race, Casse on Saturday achieved something just as notable. He trained two different horses to wins in two different classics in the same season.
“We spoke so many times about not being afraid to step out of the box, and this winter, he had been at Woodbine and he got better at Woodbine,” Casse said. “And I said to Mr. Farmer, ‘Look, he doesn’t really train like a good horse but I think we have to give him a shot. Let’s send him to the Withers [at Aqueduct]. He might be beat by 30 lengths. I can’t tell you. But if you’re OK with that, let’s do it.’ And he said yeah, let’s give it a try.”
The Withers was a fourth-place finish, which led to the Tampa Bay Derby, where he finished fifth but showed promise. Then came the Bluegrass at Keeneland and then Belmont Park and the Peter Pan.
“I said he’d love Belmont, he’ll love the big turn, a mile and an eighth and if he come running, we’ll bring him to the Belmont [Stakes],” Casse said. “And [Farmer] said it sounded like a plan … And that’s how we got here.”
Step by step — a slow start and one very strong finish, just like Sir Winston likes it.