Dave Portnoy's 30-1 longshot Lovely Grey races in Kentucky Oaks debut
Dave Portnoy, founder of Barstool Sports, made an appearance at Churchill Downs on Friday for the Kentucky Oaks. His horse, Lovely Grey, competed in the $1.5 million Grade 1 race as a 30-1 outsider. The event also drew attention to Portnoy’s eye-catching outfit, which quickly became a talking point online. Portnoy launched his racing stable, Go Go Greys Stable, in 2025 with a focus on grey horses. One of his acquisitions was Lovely Grey, a daughter of Vekoma, purchased for around $75,000. The filly initially sat on the also-eligible list but secured a spot in the Kentucky Oaks field just before the race.
At the track, Portnoy stood out in a bold, multi-coloured floral shirt paired with a navy suit. His choice of attire divided opinions on social media, with some fans praising the look while others questioned its suitability for the prestigious event. Lovely Grey entered the race as a longshot, priced at 30-1. Despite the odds, the horse’s inclusion marked a notable moment for Portnoy’s relatively new stable in a high-stakes competition.
The Kentucky Oaks saw Lovely Grey take part in one of the most valuable races in US horse racing. Portnoy’s presence, both as an owner and a fashion statement, added to the event’s buzz. The outcome of the race will determine whether his investment pays off on the track.
