Win Willy, a 56-1 shot, handed Old Fashioned the first loss of his career when he outfought the heavy favorite in the final eighth of a mile to win the $300,000 Rebel Stakes at Oaklawn Park March 14.

Previously unbeaten Old Fashioned was a 2-5 shot as the nine-horse field entered the starting gate, and he appeared to be in control after easily passing Silver City on the second turn. Win Willy then came up on the outside, seemingly out of nowhere, and passed Old Fashioned with room to spare.

Win Willy, trained by McLean Robertson and with Cliff Berry aboard, paid $115.60 on a $2 win bet. Old Fashioned held on for second, and Poltergeist was third.

Old Fashioned might have been the overall favorite for the Kentucky Derby before this race. He hadn’t lost in four career starts, including the Southwest at Oaklawn last month. This race began almost exactly as that one had, with Silver City moving to the front and Old Fashioned chasing close behind. The first quarter-mile was over in 22.54 seconds, a quick pace which might have cost the initial leaders down the stretch.