Sir Winston — Sir Winston? — has managed to cram into his 3-year-old life races at Churchill Downs, Saratoga, Woodbine, Aqueduct, Tampa Bay Downs, Keeneland and Belmont Park, where 56,217 just turned up on an absurdly beautiful Saturday without the possibility of seeing a Triple Crown champion. He hadn’t won anything since last Dec. 8. He finished fourth in the Withers on Feb. 2, fifth in the Tampa Bay Derby on March 9, seventh in the Blue Grass on April 16, and uninvited to the Kentucky Derby via a profound lack of sufficient points.
He often ran with harrumphing odds such as 33-1 and 46-1.
The 10-1 of Saturday must have seemed flattering, and here came Sir Winston, charging through the center of a bustling stretch of cavalry beneath that keen closer Joel Rosario to hold off a tardy threat from Bill Mott’s favorite, Tacitus, in a measured 2:28.30. “Yeah, I didn’t think that was the one,” to fear, the Hall of Fame trainer Mott said. “I thought Mark Casse had a big shot, but I didn’t know it was this one. I guess that’s what keeps the game interesting.”
Casse, 58, would be the trainer with the infectious personality and the keen storytelling skill who just got his first big-three win three weeks ago with War of Will in the Preakness. War of Will ran Saturday, becoming the only horse to enter all three races this year, but he ran glumly and ran ninth (out of 10). As they went and Joevia grabbed the early lead as expected, Casse noticed War of Will in good position and bad mind-set. He felt briefly sad. He turned his attention to Sir Winston.
“At this time last year,” Casse would say, “if you asked me to rate our top 20 2-year-olds, [Sir Winston] would have been about 16th or 17th. I’m very proud of him because I feel like he’s what our organization represents, because I feel like we develop horses.”
This qualified as serious development. Sir Winston himself finished ninth of 10 one day last July at Saratoga, far enough back he might as well have been in Rochester, whereupon Casse said to Tracy Farmer, the Kentuckian owner who also bred Sir Winston, “Don’t give up on him. It’s crazy, but I see something.”
Come April at Keeneland in Lexington, he did not resemble someone who might send Wood Memorial winner Tacitus to a pretty good Belmont Stakes second place to go with his pretty good Kentucky Derby fourth place. Keeneland was “so speed-biased,” and “nobody was closing,” Casse said, so Sir Winston “just kind of ran around there.”
There went the Derby, so they aimed him for the Peter Pan of May 11 at Belmont, where he finished second and where, four weeks after that, he would become the sixth Belmont Stakes winner this century to join the Triple Crown crowd only at its last gathering. He would relegate Tacitus to a second-place Belmont to go with his Derby fourth, plus Joevia to third, Tax to fourth and the Japanese hopeful Master Fencer to fifth. “He’s not a big horse,” Casse’s assistant trainer Jamie Begg said, “but he’s really filled out a lot,” even since the Peter Pan.
Further, Sir Winston joined Tacitus in a fleeting, closing moment of possibility. As Tacitus gained ground too late, it grew clear either Casse or Mott would claim two-thirds of this eccentric Triple Crown. Mott took the Kentucky Derby with Country House after the disqualification for interference of the apparent winner, Maximum Security, with neither racing since. Casse took the Preakness with War of Will, whom Maximum Security had inconvenienced the most among the voluminous Derby rivals.
That had left Casse outside the barns at Churchill Downs on that Sunday morning, May 5, exhaling at how horse racing had escaped a catastrophe that controversial day. Now Mott and Casse had a strangely dramatic Triple Crown season on which to reflect.
“I don’t know,” Mott said. “It’s been a mixed bag for sure. In a sense it’s been a good Triple Crown. I guess that’s a lot of horses that had a good chance.” Minutes after that, asked to peg a best in show from the hodgepodge, Casse thought about it after his own sublime Triple Crown and said, “I think probably everybody’ll go back to Maximum Security, won’t they?”