Jack Sisterson Talks Vexatious, Returning Calumet to Glory On TDN Writers’ Room


Jack Sisterson with Lexitonian (Speightstown), runner-up in Saturday’s GI Bing Crosby S. | Sarah Andrew

Two years ago, when it was announced that legendary Calumet Farm was hiring Jack Sisterson as its primary trainer, there was skepticism. At just 33 years old, with only experience as an assistant to his name, it was fair to question whether or not Sisterson was prepared to carry the flag for such a powerful racing and breeding brand. Those questions have now been answered–resoundingly in the affirmative, as just a short while later, Sisterson has not only proved equal to the task, but appears on his way to the even larger accomplishment of restoring historic Calumet to the glory of its heyday.

Still in the afterglow of pulling off a colossal upset of champion Midnight Bisou (Midnight Lute) with Calumet’s Vexatious (Giant’s Causeway) in the GI Personal Ensign S. at Saratoga, Sisterson joined the TDN Writers’ Room podcast presented by Keeneland Wednesday to talk about his first Grade I victory, his hands-on education in racing and the bright future for him and Calumet.

Calling in via Zoom as the Green Group Guest of the Week, Sisterson spoke on how he adapted his training approach to fit Vexatious, who is reaching her career peak at the age of six.

“She has an extremely high cruising speed, and she can carry that over a distance of ground,” he said. “What we found with her, she’s a filly that loves to train at 5:30. She goes right out when the track opens, because that’s what she wants. She’s very businesslike and wants to get on with it. And when I initially got her, if I asked her to go three-quarters of a mile in a workout, she would put so much effort into it that she was doing too much in the mornings and not leaving it for the afternoon. So we decided to back up all of her works to half a mile and crossed our fingers that would result in her being a little bit more energetic in the afternoons. It’s slightly worrisome when you just breeze them half a mile–do they have enough foundation in them to compete at that classic type of distance on the dirt? But with her, she puts so much effort into her gallops and half-mile breezes that she’s in that happy stage of her career at the moment.”

Asked about the process that led to his hiring by Calumet, Sisterson credited former boss Doug O’Neill and compared the aura of Calumet to another iconic brand from his upbringing playing soccer in England.

“Initially, when I had this small conversation with them, I’d never been to the farm before,” he said. “I was working for Doug at the time, who still to this day is very supportive of everything I do, which I’m very grateful for. It was Doug who pushed me out there, saying, ‘If you don’t do it, I’m going to do it.’ Being from England and a soccer player, when you grow up, there’s Manchester United, at the top of the league with so much history and success. I assumed Calumet was the Manchester United of farms. Why would they want someone like me? I’m nobody. It was honoring, humbling. I’m just a very, very, very small piece of so much hard work that goes in behind the scenes that people don’t see.”

It was soccer that first brought Sisterson to the United States and sent him on his path to stardom in the Thoroughbred racing world. Having a lifelong passion for both sports, Sisterson killed two birds with one stone by enrolling at the University of Louisville, which led to a first racing gig working alongside a Hall of Fame trainer.

“From as far as I can remember, there was racing on TV or we were going to some big racing events in the Northeast of England,” he recalled. “I fell in love with it from day one and always wanted to have some involvement in it. I was fortunate enough to be offered a soccer scholarship at Louisville, which offered the equine program. And in return, I worked summers for Todd Pletcher. That was my first introduction to the American side of racing.”

Elsewhere on the show, the writers analyzed last weekend’s major stakes action, previewed Saturday’s GI Runhappy Travers S. and took stock of where the 3-year-old picture stands exactly one month away from the GI Kentucky Derby. Then, in the West Point Thoroughbreds news segment, they reacted to the news of increased restrictions on out-of-state jockeys attempting the ride in the Derby, even as fans are still slated to be on track with much more lax requirements. Click here to watch the podcast on Vimeo, and click here for the audio-only version.

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