Mark Casse admits he's in somewhat uncharted waters.
Canadian thoroughbred racing's top trainer an unprecedented 11 times — and for the last eight consecutive years — is preparing Sir Winston, last year's Belmont Stakes winner, for next month's US$12-million Dubai World Cup at Meydan Racecourse. Sir Winston, who broke his maiden at Toronto's Woodbine Racetrack and also earned his first stakes race there, will become just the second Casse-conditioned horse to make the trip to the United Arab Emirates.
The first was two years ago when Holding Gold finished seventh among 13 horses in the Grade 1 US$2-million Al Quoz Sprint turf event at Meydan.
"I've only gone to Dubai once and just kind of had OK success," Casse said in a telephone interview. "So it's kind of uncharted territory for me.
"But Sir Winston is happy and he's training well."
The four-year-old son of Canadian Horse Racing Hall of Famer Awesome Again heads to Dubai off a 2 1/4-length win in his last race, an US$80,000 allowance event over a mile Jan. 31 at Aqueduct. Sir Winston rallied from last to top the seven-horse field in his second start following a length layoff.
"To be honest, I didn't expect him to run quite as well as he did," Casse said. "I was impressed because I was concerned it was going to be too short for him and it wasn't.
"Even though there wasn't outstanding horses in the race, you're still running against horses that are at the top of their game. There isn't a whole lot of difference between a decent horse and a very good horse."
Sir Winston was off for more than six months after winning the Belmont on June 8 due to a left front ankle injury. He returned Dec. 28 but was last in the 12-horse field _ later elevated to 11th via disqualification _ in the $75,000 Woodchopper Stakes, a mile-long turf race.
So why run in the Dubai World Cup, a 1 1/4-mile dirt race?
"Well, there's 12 million reasons," Casse said matter-of-factly. "It's a great distance for him and I think with where he is right now in his training, it's a good time to take a shot.
"The third start off a layoff is always a question. But all of the signals say he's supposed to run a huge race and if he runs a huge one, there's a very large reward."
Tyler Gaffalione will be aboard Sir Winston in Dubai. He'll become the eighth different jockey to ride Sir Winston, who has only run 12 times.
Joel Rosario rode Sir Winston in the Belmont while Dylan Davis was aboard for last month's victory at Aqueduct.
"Joel would've been our first choice," Casse said. "Dylan and Tyler are both young riders but the difference is Tyler has ridden at Royal Ascot, he's ridden in the Preakness and the Derby.
"I just felt like when you go over there you want a guy who has ridden in the big races and has that type of exposure. Tyler also has communication, respect and rapport with our team. We talked about taking Dylan, he was under consideration and I think three or four years down the road you're probably going see other riders off for Dylan but he's not quite there yet."
Sir Winston has four wins, a second and third over 12 career starts with earnings over US$1 million.
Casse had Sir Winston at his farm in Ocala, Fla., but Thursday sent him to Palm Meadows training centre in south Florida. Casse said the move was made to better simulate weather conditions the horse will face in Dubai.
"Believe it or not, it's a lot warmer in south Florida than it is in Ocala in the winter . . . it could be a difference of 15-to-20 degrees (Fahrenheit).
"The idea is to get him to the warmer weather."
Casse said he expects Sir Winston to leave for Dubai sometime around March 17.
"That actually borders on a little too long," he said. "When we go to California, we prefer to go out three or four days (in advance of race) but obviously Dubai is a lot further.
"We're doing the same thing everyone else is doing."
Something Casse isn't concerned about is how Sir Winston will handle the long trip.
"No, not really," he said. "It doesn't work for every horse but he's very laid back, he doesn't care."
This report by The Canadian Press was first published Feb. 27, 2020.
Dan Ralph, The Canadian Press