Jersey Jerry joins Russell Wilson's winners circle at Saratoga

TLDR: Russell Wilson's first horse as an owner won at Saratoga on Travers Day, and Barstool's Jersey Jerry somehow ended up in the winners circle to celebrate it with him.
Russell Wilson walked away from a 14-year NFL run through Seattle, Denver, Pittsburgh and New York, and his next act is apparently thoroughbred ownership. Under the name Three Brand Racing, Wilson bought into two 2-year-olds this year: a colt named Club Reign, picked up for $475,000, and a filly called Rugged and Wise. Club Reign made his career debut on August 29 in the first race of the Travers Day card at Saratoga, a 12-1 longshot in an 8-horse field of first-time starters.
He won. Club Reign bobbled at the break, pressed the pace anyway, and crossed first in a 6-furlong maiden special weight, paying $18.72. That's the win that put Russell Wilson in a Saratoga winners circle for the first time as an owner, and somehow Barstool's Jersey Jerry (@Jerrythekid21) was standing right next to him for it.
Big Cat (@BarstoolBigCat) was on the scene documenting the whole thing in real time, and once Club Reign crossed the wire, he made sure everyone knew exactly where his guy had landed: 'Jerry in @DangeRussWilson's winners circle!'. It's the kind of access most fans never get — the actual connections' circle, right after the horse they own just won.
Rico Bo$co (@Return_Of_RB), Jerry's Jerry TerRy Show co-host, was watching the whole thing unfold from afar and couldn't help but crack a joke about the exclusivity of it all: if there was only room for one person from the show in that winners circle, he was glad it was Jerry. It's a bit, but it's also true — Wilson's family was packed into that circle for a horse that just won at 12-1, and Jerry got the invite anyway.
Jerry, for his part, spent the day leaning all the way into the moment, captioning his posts with lines like 'It was ALWAYS RUSSY!!!!' and 'We ride with Russy!!!!!' — the kind of confidence that's easy to have after the fact, but nobody's arguing with a 12-1 winner.
Wilson's brother Harry reportedly sparked the family's interest in racing after connecting with bloodstock agents at this year's Kentucky Derby, and by all accounts Wilson has been hands-on ever since, checking in daily on both horses rather than just cutting checks. One win into ownership, with a Barstool host already embedded in the winners circle, it's a safe bet this isn't the last Saratoga trip for either of them.
More Stories
Internet Invitational episode 1: Jon Gruden, Johnny Manziel
Jersey Jerry, Big Cat Cowboys vs. Eagles MNF picks graded
Cody Franke tribute opens 2026 Internet Invitational
Kevin Kisner The Duke swing Internet Invitational episode 1
Malosi Togisala rangefinder tape Internet Invitational
Nick Fasoli back for Internet Invitational 2026 episode 1


