“I saw War of Will was getting weary,” Casse said, “so I started riding Sir Winston.”
Sir Winston, named by owner Tracy Farmer for the great 20th-century British Prime Minister Winston Churchill, was viewed as Casse’s other horse in the $1.5 million Belmont despite the potential Farmer spotted. But he received a flawless ride from Joel Rosario while Tacitus, with Jose Ortiz aboard, was forced wide on both turns. The lost ground made the difference.
“We did have a bit of a wide trip, which you never like,” said Bill Mott, who trains Tacitus. “He came running and looked like he finished better than anybody. We planned to try and be in contention at the quarter pole, which he was. He just couldn’t get there.”
Sir Winston, a son of Awesome Again, won for only the third time in 10 career starts. This was his first victory on dirt. His previous two successes came on a synthetic surface main track at Woodbine as a 2-year-old.
The colt initially showed little as a homebred for Farmer, finishing sixth of seven when he debuted at five furlongs last June 14 at Churchill Downs and then ninth of 10 on July 21 at a mile and a sixteenth on the turf at Saratoga Race Course.
“At this time last year, if you had asked me to rate our top 20 2-year-olds, he would have been 16th or 17th ,” recalled Casse.
Casse prides himself on his operation’s ability to develop prospects. This colt was a project he and his staff embraced. He said he remembers telling Farmer, “Don’t give up on him. It’s crazy, but I see something.”
Casse targeted the Kentucky Derby Presented by Woodford Reserve for Sir Winston because he was sure he would relish distance, but the youngster did not come close to accumulating enough qualifying points earlier this year to make the cut for the 20-horse field. He ran fourth in the Withers Stakes, fifth to triumphant Tacitus in the Lambholm South Tampa Bay Derby, and seventh, 19 ¼ lengths back, in the Toyota Blue Grass Stakes.
Casse was undaunted. He started the chestnut Kentucky-bred in the 1 1/8-mile Peter Pan Stakes on May 11, vowing to go on to the Belmont only if the 3-year-old showed he belonged. A runner-up finish behind Global Campaign provided evidence enough that he at least deserved a shot.
Still, Casse had expressed concern in the days leading to the Triple Crown finale about Sir Winston’s prospects if the pace proved to be slow. Longshot Joevia indeed set sluggish fractions – the opening half mile went in a cozy 48.79 seconds – but Rosario was able to keep his mount within striking distance, and they pounced at an opportune time.
Sir Winston completed the mile and a half in 2:28.30. He paid $22.40 for a $2 win wager. Joevia stayed on fairly well for third. Tax, a former $50,000 claimer, acquitted himself well to be fourth. War of Will, the only 3-year-old to compete in all three of the Triple Crown races, seemingly paid a steep price for that. He never fired and faded to ninth in the field of 10.
“He was in a nice rhythm and, approaching the quarter pole, I squeezed on him a little bit and he just didn’t have that punch like he normally does,” said War of Will’s jockey Tyler Gaffalione. “Today just wasn’t his day. It’s hard to say if it (three races in five weeks) took its toll, but I would definitely take that into account.”