‘He Could Do Just About Anything’: Belmont Stakes Winner Sir Winston Enters A New Frontier At Stud

Ever since he first set foot on the racetrack, Sir Winston's modus operandi has centered around defying expectations.

He was an unorthodox pick for the 2019 Belmont Stakes after his highest career achievement up to that point came over the all-weather Tapeta surface at Woodbine. Then, he won the biggest race of his life.

Owner and breeder Tracy Farmer elected to keep the horse in training long after others in the fraternity of Belmont Stakes winners tend to stick around, and he maintained his form admirably, including a victory in the Grade 3 Valedictory Stakes at Woodbine at age five.

Now that he's entered his first season at stud at Crestwood Farm in Lexington, Ky., Sir Winston's next hurdle isn't one he can outrun, but one he best conquers standing still.

Sir Winston is a son of Awesome Again, out of the Grade 3-winning Afleet Alex mare La Gran Bailadora. Awesome Again and Afleet Alex both stood about 16 hands tall, and for all the tales a person can spin about how Northern Dancer revolutionized the breed at a diminutive 15.2 hands tall, the modern commercial market can struggle to wrap its mind around a stallion prospect that lacks scope.

Crestwood's Marc McLean had the same reservations when Farmer approached the stallion operation about standing Sir Winston, putting two and two together with his pedigree. Then, he got a look at the horse in the flesh, and those concerns disappeared.

“That was going to be our first question – is he a squatty horse?” McLean said. “Because you see Afleet Alex and you see Awesome Again, and he's not that. He's 16.2 (hands tall) with size and scope, and he's got a lot of leg.”

McLean said it was common for breeders to have the same preconceived notions of what they thought Sir Winston would look like before they booked their visits, then need to change their playbook once the horse exited his stall. Sir Winston is about as leggy as they come for a son of Awesome Again, and he's got a solid foot under him. McLean said he could work with that.

“In this market, that's what people want,” McLean said. “That's nice that you get that ahead of time. You can breed a decent-sized mare to him, and not get a shrimp.”

The deal to stand Sir Winston came together rather quickly, with Farmer contacting Crestwood around the time of last year's Keeneland September Yearling Sale.

Farmer, who keeps about 15 mares at his Shadowlawn Farm in Midway, Ky., in addition to his successful racing stable, had sent mares to be bred to Crestwood stallions in the past, but McLean said that was about as far as their professional relationship went before standing Sir Winston.

“He just asked if we'd be interested, and we said, 'absolutely,'” McLean said. “Then, we went and sat down and hammered it out. We were thrilled that he came to us.”

Sir Winston won six of 20 starts during his on-track career with trainer Mark Casse, and he earned $1,277,623.

The Belmont Stakes is obviously Sir Winston's biggest triumph, but the remainder of his resume helps give depth to his resume. Each of his six wins, and all five of his additional career placings, came at a mile or longer. He won the Display Stakes at Woodbine as a 2-year-old after finishing third in the G3 Grey Stakes, and he added to his dirt credentials with a runner-up effort behind Global Campaign prior to his classic score, and another second-place finish in the Flat Out Stakes at the same track a year later.

Sir Winston continued to run at a high level at age four, highlighted by a hard-fought half-length score in the G3 Valedictory Stakes at Woodbine in what would be his penultimate start.

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As one of the final racetrack stars sired by the late Awesome Again, Sir Winston joins a shrinking fraternity of his sons at stud in Kentucky. Calumet Farm has a pair of them in Preakness Stakes winner Oxbow and Bravazo, WinStar Farm stands Paynter, and Hill 'n' Dale Farms has Horse of the Year Ghostzapper.

Ghostzapper is the obvious standout among that group, but Paynter sired 2021 Horse of the Year Knicks Go, Oxbow sired Grade 1 winner Hot Rod Charlie, and Bravazo will see his first 2-year-olds hit the track in 2024.

Despite those accomplishments, McLean said there was still plenty of room for Sir Winston to add to the legacy of the Awesome Again sire line.

“I don't know that [Awesome Again] gets the respect that he should still be getting,” he said. “You look at Ghostzapper, and he's still got top horses, and he's a great broodmare sire. Hopefully [Sir Winston's] the next one that will carry it on, and he's got the female family to do it.”

That female family includes Grade 3-placed stakes-winning second dam Affirmed Dancer and Canadian champion third dam Woolloomooloo. Italian 2,000 Guineas winner Southern Arrow can be found further down the page.

McLean said Crestwood had purchased mares during the November mixed sales to support Sir Winston, and Farmer would be backing up the stallion with his own mares.

As for what might work best with the Belmont winner, McLean suggested Sir Winston has the makings of a multi-tool stallion.

“You could put a nice speedy type into him, as far as a body type, a short coupled, muscular type, and he's going to stretch it out and make it taller,” he said. “I think you could go in pretty much any direction since he's a medium-sized horse. With the mares we're picking out of our own, we thought he could do about anything.

“We'll go with a middle-aged mare that's been a good producer that we know gets good-looking babies, and some younger mares that are just joining the broodmare program,” McLean continued. “We like mares with deep families. We like to see sisters producing, so that's something that we like keying in on.”

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