There's something different about Mike Repole this time around. The self-made billionaire from Queens, known as much for his unfiltered opinions as his neon blue-and-orange silks, is back at Churchill Downs with the Kentucky Derby favorite—a horse named Renegade. And if you know Repole, you know that name fits perfectly.

For 15 years, Repole has chased the Derby dream with spectacular near-misses and gut-wrenching luck. But this year feels different. His 80-something parents are making the trip. He's partnered with longtime horse folks Robert and Lawana Low, who bred Renegade and jumped at Repole's offer to buy back half the horse. Jockey Irad Ortiz, one of the sport's all-time greats, is in the saddle. And that No. 1 post position—the one that hasn't produced a winner in 40 years? Repole sees it as karmic, not cursed.

"Maybe there's something meant to be about this race and this horse," Repole said Thursday, standing outside Todd Pletcher's barn on the backstretch.

Repole is no stranger to shaking things up. He calls himself "The Commissioner"—a jab at a sport he believes lacks leadership. He's the kind of owner who shows up at the Derby handing out tickets to United Football League games (yes, he's remaking that league too) and then casually mentions he's planning to file a lawsuit against The Jockey Club, the century-old organization he says is blocking progress in horse racing.

Love him or hate him, Repole brings energy to a sport that often plays it safe. And if Renegade crosses the finish line first on Saturday, it won't just be a win for the horse. It'll be a win for every outsider who ever dared to take on the establishment.