She’s a long shot, but Dave Portnoy is happy to have a horse in the race.
The Barstool Sports founder’s filly, No. 15 Lovely Grey, is officially in the gate for Friday’s Kentucky Oaks, sliding into the $1.5 million Grade 1 race after a late scratch shook up the field.
The door opened when Bottle of Rouge — one of the race’s more accomplished contenders — was withdrawn after developing a cough following a weekend workout at Churchill Downs. Lovely Grey was previously stuck on the also-eligible list.
Lovely Grey is listed at 30-1 morning line odds in the Oaks, a race exclusively for three-year-old fillies that precedes the Kentucky Derby.
“My horse Lovely Grey is an extreme longshot. I don’t care,” Portnoy posted to Instagram on Wednesday night. “All you need is a chip and a chair. Im proud of her win lose or draw. She’ll prob be at least 30-1 unless the Stoolies bet her down. If it was a beauty pageant she’d win in a landslide.”
Most of the bets for the Kentucky Oaks won’t come in until right before Friday’s race (post-time is 8:40 p.m. ET), but the early money is unsurprisingly coming in on the polarizing media mogul’s entry.
A midday update on the odds for the Oaks had Lovely Grey all the way down to 6-1, which suggests that Stoolies were eager to get money down on Portnoy’s horse.
Because horse racing uses parimutuel wagering, which means that payouts are not fixed, like in sports betting, but instead are determined by the final ratio of money wagered, we could see an interesting scenario when a horse that was projected as a long shot winds up as one of the favorites, just because of the popularity of its owner.
That will also prop up the prices on other horses, which means we could see some tempting prices on contenders.
Portnoy operates under the banner of “Go Go Greys Stable,” a racing outfit built around his stated strategy of exclusively buying gray horses. It’s a passion project he began in 2025, having purchased other gray fillies in development such as Wondergirl Carly, who won her career debut in October, Miss Watermelon, and Mr. Pistachio.
Lovely Grey didn’t arrive with big-auction hype. She was acquired privately by Portnoy after failing to meet her reserve at a yearling sale, where bidding stalled at $75,000 — effectively making her a pass-over before joining his stable.
The filly is a daughter of Vekoma, who finished 12th in the 2019 Kentucky Derby. She will be saddled by trainer Kelsey Danner and ridden by jockey Dylan Davis.
No female trainer has ever won the Kentucky Oaks.
Lovely Grey enters the Oaks off a runner-up finish in the Bourbonette Oaks at Turfway Park on March 21.
On paper, her resume doesn’t quite stack up with the heavy hitters. Lovely Grey has one win and $148,668 in earnings throughout seven career starts.
Friday will mark her first attempt on a fast dirt track, a significant unknown for a filly who has spent most of her career on turf and synthetic surfaces. Her lone dirt start came in less-than-ideal conditions — a sloppy debut at Horseshoe Indianapolis, where she finished in fourth place.
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