Classic Winner Sir Winston Looks to Surprise in Pegasus

Tracy Farmer homebred Sir Winston  is on course for a start in the $3 million Pegasus World Cup Invitational Stakes (G1) Jan. 29 at Gulfstream Park, 2 1/2 years after achieving his career highlight with a 10-1 upset victory in the 2019 Belmont Stakes (G1).

Among the son of Awesome Again's victims in the third leg of the 2019 Triple Crown were War of Will  , his more celebrated stablemate in the barn of Hall of Fame trainer Mark Casse. War of Will entered the Belmont off a victory in the Preakness Stakes (G1).

"I told people before the Belmont, 'I think you're missing somebody.' I said, 'It wouldn't shock me if he won.' He was doing really well," Casse said. "I kind of feel the same way now. I think he's really back to himself and doing really well."

Since prevailing in the Belmont, Sir Winston, who is scheduled to take on likely 2021 Horse of the Year and 2021 Pegasus winner Knicks Go   as well as Big Ass Fans Breeders' Cup Dirt Mile (G1) winner Life Is Good  in a star-studded Pegasus World Cup field, has experienced some rough moments. None proved more costly than a futile trip to Dubai, where the 2020 Dubai World Cup (G1) was canceled less than a week before the race because of the burgeoning COVID-19 pandemic.

"We took him to Dubai. We were a few days from running and they canceled the Dubai World Cup. We brought him back and it really knocked him on his rear," Casse said. "He just didn't come back the same horse. We ran him a few times and he didn't run great. We just sent him home to Tracy's farm and gave him a long time off. He's come back and has gotten better and better."

Sir Winston was out of action for just shy of a year but returned to the races a happier horse for a four-race 2021 campaign at Woodbine. The Kentucky homebred impressively won an Aug. 19 allowance, before finishing a close second in both the Durham Cup (G3) and the Autumn (G2) stakes. He capped off his successful season with a victory in the 1 1/2-mile Valedictory Stakes (G3) Dec. 5.

This year he has regularly been working at Palm Meadows—including a half-mile move in :47 4/5 there Jan. 20 to earn the bullet—as he prepares for the 1 1/8-mile Pegasus.

"He got a little unlucky in a couple spots. For him to win at a mile-and-a-sixteenth, he needs to have a pretty good pace. He needs things to go his way," Casse said. "He could have easily won a couple more last year."

Casse has seen enthusiasm from Sir Winston during his comeback.

"It's funny but I think he enjoys his job now more than before," Casse said. "He's very professional. He always has been, but he trains better, acts better. This is going to be a heck of a race. Hopefully, we can get a piece of the pie."

Sir Winston figures to race off the early pace in the Pegasus, well behind speedy Knicks Go and Life Is Good, the front-running winner of the Breeders' Cup Dirt Mile (G1).

"It looks like there will be some serious pace. Obviously, he needs a lot of things to go his way," Casse said. "He's feeling really well, and we believe he deserves a chance."

Casse is hopeful Sir Winston will be able to pull off his second big upset 2 1/2 years later in the Pegasus World Cup.