Woodbine To World Cup: Sir Winston Primed For Pegasus

January 25, 2022

Fans of Woodbine racing have a horse to cheer for in the Pegasus World Cup.

Sir Winston, who has contested seven of his 19 career starts at Woodbine, is set to square off against a star-stacked field, including last year’s winner Knicks Go, in the Grade 1, $3 million Pegasus World Cup on January 29 at Gulfstream Park.

“Woodbine is what got Sir Winston started,” said dual Hall of Famer trainer Casse, of the 2019 Belmont Stakes champion. “He was struggling as a young horse and we brought him to Woodbine. He got good and then went on and won the Belmont.”

After making his first two career starts south of the border in 2018, the son of Awesome Again made three starts at Woodbine, winning two of three, including a victory in the Display Stakes, in what was the final start of his two-year-old campaign.

“I think he’s an overachiever,” said Casse. “I always tell the story where he got beat 20 lengths his first two starts and then went on to win the Belmont. He’s always going to be special in my heart for that reason. He tries. He’s not an imposing horse. He’s an average-looking horse and became much better-looking as he got older.”

Bred and owned by Tracy Farmer, Sir Winston hit his best stride at Woodbine in 2021 after returning from an 11 ½-month hiatus from racing. He was sent to the sidelines near the end of 2020 before he loaded into the starting gate last August where he won an allowance race.

His past four engagements, three of them stakes, have all come at the Toronto oval, yielding two wins and a pair of seconds.

Sir Winston closed out his five-year-old season with runner-up performances in the Grade 3 Durham Cup and Grade 2 Autumn at Woodbine before a smart score in the Grade 3 Valedictory Stakes, over 1 ½ miles, on December 5.

“The Valedictory, of course,” offered Casse, as to which 2021 win was the most impressive. “For Sir Winston, it was a little frustrating. A couple of times he got a little unlucky and I thought he could have won. The problem with Sir Winston is that a mile and a sixteenth is a little short for him. He would kick-in and everyone would sprint home and he would start kicking and then he’s kind of run into traffic. It wasn’t the rider’s fault. He just doesn’t have that quick, responsive acceleration. But he’s a hard-trying horse.”

He has also overcome his fair share of adversity.

“We had him in Dubai. He was supposed to run in the 2020 World Cup and then they canceled it. He just didn’t come back the same horse from Dubai. It took us a long time to get him back. We had to make a decision as to whether to retire him or give him a long break. So, we sent him back to the Farmer’s place and he spent a lot of time there. Kudos to their farm because he came back a better horse.”  

After the Valedictory triumph, Sir Winston headed back to south Florida to be with Casse, where he has been working over the dirt at Palm Meadows Training Center. On January 7, he travelled five panels in 1:00.55, the second quickest of 27 moves at the distance. 

Sir Winston arrives at the Pegasus with a 6-4-1 mark from 19 starts, with earnings of $1,189,873.

“In 2021, he gave me everything he had every time,” praised Casse.

He’s hoping for similar good fortune this year, starting on January 29 in the Sunshine State.

“For a different and unique perspective on horse racing, I read Jonathan Stettin’s Past the Wire.” Mike Smith, Hall of Fame, Triple Crown winning jockey

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