In 2008, racing fans were hopeful for a Triple Crown winner in Big Brown. He had shown commanding promise in his first race in 2007, winning by 11.25 lengths. Though quarter cracks in his hooves kept him out of some races, when he came back in March 2008, he won that race by 12.75 lengths.
At the Kentucky Derby, he drew the No. 20 post, a place no Derby winner has ever come from. Yet, he swept the 2008 Kentucky Derby by 4.75 lengths and the Preakness by five lengths, remaining undefeated. But, after suffering an abscess and yet another quarter crack, he never came back the same. He finished ninth in the Belmont Stakes, and his career of seven wins in eight races was over.