Barstool Sports founder Dave Portnoy turned heads at Churchill Downs on Friday after debuting a flamboyant outfit for the Kentucky Oaks.
The self-proclaimed ‘El Presidente’ arrived in Louisville to watch his horse, Lovely Grey, compete in the prestigious $1.5 million Grade 1 race.
Portnoy opted for a vibrant, multi-colored floral shirt along with a navy suit for the occasion, before being spotted chatting with patrons as he prepared for the race.
It didn’t take long for the outfit to spark a heated debate on social media, with fans split over the bold choice from the Barstool boss.
Taking to X, one fan wrote: ‘Love the suit and undershirt tropical vibes!!’
Similarly, another user online said: ‘Looking sharp! How exciting! I hope she wins.’
Barstool Sports founder Dave Portnoy turned heads at Churchill Downs on Friday
Portnoy opted for a vibrant, multi-colored floral shirt along with a navy suit at Kentucky Oaks
However, not everyone was as keen on Portnoy’s race day attire.
‘You guys look like you’re headed to a shoe salesman convention!’, one user said in response to a picture Portnoy shared on social media.
Bluntly, another fan wrote: ‘Suit too small Dave’.
Portnoy’s filly, Lovely Grey, officially drew into the field following a late scratch, moving up from the also-eligible list on Thursday.
Despite being a 30-1 longshot, the horse has seen a surge in betting interest from ‘Stoolies’ eager to back Portnoy’s stable.
Taking to his Instagram on Wednesday, Portnoy wrote: ‘My horse Lovely Grey is an extreme longshot. I don’t care.
‘All you need is a chip and a chair. I’m 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,’ he added.
The media mogul launched his ‘Go Go Greys Stable’ in 2025, a passion project focused on a unique strategy of exclusively purchasing gray horses.
Lovely Grey, a daughter of Vekoma, was acquired privately by Portnoy for approximately $75,000 after initially failing to meet her reserve at auction.
