Rejuvenated Sir Winston Returns to Dirt for Pegasus

Trainer Mark Casse has a disagreement with author Thomas Wolfe.

Casse believes you can indeed go home again and he's intent on proving it in no less of a setting than Jan. 29 at Gulfstream Park in the $3 million Pegasus World Cup Invitational Stakes Presented by 1/ST BET (G1) with his classic winner Sir Winston .

Most racing fans remember Tracy Farmer's Sir Winston as the winner of the 2019 Belmont Stakes (G1). Some of those fans might also have thought that the 6-year-old horse had been retired after closing 2020 with a pair of unplaced finishes.

"He's the only winner of a Triple Crown race still in training," Casse points out. 

What has kept him at the races is something surprising, unless you are well-versed on his past performances or follow racing in Canada on a surface that has brought out the best in Sir Winston.

What tends to be overlooked is that the homebred son of Awesome Again  first moved into the fast lane as a 2-year-old when he started racing on the synthetic surface at Woodbine. 

Prior to that, in his first two starts Sir Winston was sixth on dirt at Churchill Downs and ninth on turf at Saratoga Race Course. But after he was shipped to Woodbine and shifted to the all-weather course there, he posted a maiden win, was third in the Grey Stakes (G3), and closed out his juvenile season with a victory in the Display Stakes.

"He found his form at Woodbine," Casse said.

After that, Casse returned Sir Winston to dirt and was ultimately rewarded with a second in the Peter Pan Stakes (G3) at Belmont Park that set up his Triple Crown score in the Belmont.

But after that, little went right for him. An ankle injury sidelined him until December, when his comeback start was an 11th in the Woodchopper Stakes on turf. After an allowance optional claiming win at Aqueduct Racetrack to start 2020, he was shipped to the Middle East for the Dubai World Cup Sponsored by Emirates Airline (G1) but became stranded there when the race was cancelled due to the COVID-19 outbreak. 

When he returned to the United States, his luck did not change. After a second in the Flat Out Stakes, he was sixth by 21 1/2 lengths in the Suburban Stakes (G2) over the same surface he ran to glory over in the Belmont Stakes and then was fourth by 20 3/4 lengths in the Champions Day Marathon Overnight Stakes Presented by Thoroughbred Aftercare Alliance at Churchill Downs.

"It looked like he didn't want to be a racehorse anymore," Casse said. "That trip to Dubai was extremely hard on him and he never rebounded."

That brought Farmer and Casse to a crossroads. Do they retire him, or give him a last chance to resurrect his racing career? Farmer opted to keep him in training.

"Tracy is a real sportsman," Casse said. "As much as a lot of people would have been tempted to retire him and make him a stallion, Tracy loves racing and wanted to keep running him."

So, after the reset button was pushed, Casse decided to send Sir Winston to the friendly confines of Woodbine.

"Sometimes you have to go home to get started again," Casse said.

Thus, after some freshening at Farmer's farm, Sir Winston was sent to Canada for a rejuvenating return to Woodbine's all-weather track.

The results to date have favored Casse over Wolfe as Sir Winston registered two wins and a pair of seconds in four 2021 starts, capped by a win in the Dec. 5 Valedictory Stakes (G3) to give him a mark of six wins in 19 career starts.

Inspired by those efforts, Casse is hoping there will be some déjà vu Saturday when Sir Winston returns to the United States and dirt racing for the Pegasus.

"I don't see why he won't do well on dirt," Casse said. "He's got a new lease on life."

In facing Knicks Go   and Life Is Good  in the 1 1/8-mile Pegasus, Sir Winston figures to face the biggest challenge of his career. His morning line odds of 12-1 clearly reflect that.

"Anybody that handicaps the race knows he will have to run the race of his life to win the Pegasus," Casse said. "We understand that. But we're there. If you're not in it, you can't win it. I feel he's trained well and I think he'll give a good showing of himself. Where that puts him in this field, I'm not sure."

On the bright side, the son of the Afleet Alex  mare La Gran Bailadora and lone winner from his dam's six foals is helped by having late speed in a race where the two speedy favorites should be battling from the start. If the factions get out of hand, perhaps Sir Winston can benefit from it. It's a plausible theory, but Casse knows that's easier said than done.

"That's what everyone else is hoping for," Casse said about the prospect of a heated pace duel between Knicks Go and Life Is Good. "I don't see it happening, but we can hope for it."

And if that hope does not work out, there's always the possibility of a return to Woodbine, where Sir Winston knows he can indeed go home again.