At 5'3", Desormeaux has said his natural weight would be about 135 pounds, and that he has occasionally had trouble keeping at a riding weight of around 115 pounds. "All jockeys think about food all the time," he stated once. And his fall in 1992 left him with a permanent hearing deficit in one ear. But above all, he had a long struggle with alcohol use, for which the racing industry maintains a low raceday tolerance due to the high risk of the sport. Desormeaux failed breathalyzer tests in 2010 at Woodbine, and in 2012 at Belmont Park, the latter costing him mounts in the Preakness and Belmont that year. The alcohol issues led many trainers to shy away from using him. "It was a tough decision on the personal level because we're friends. But it wasn't a tough decision on the business level", explained trainer Dale Romans. "When the good Kent shows up, he is the best rider in the country and one of the best of all time. That's what the shame of it is." On August 31, 2011, Desormeaux was arrested when he tapped a NYRA security guard with his car at Saratoga Race Course. Charged with second degree reckless endangerment, he later pleaded guilty to a reduced charge of disorderly conduct. His opportunities continued to dry up, causing his rank by North American earnings to drop from 15th in 2010 to 99th in 2013. In 2014, he failed to crack the top 100 for the first time in his career. In the summer of 2014, Keith Desormeaux helped bring Kent back into the limelight by offering the ride on a promising colt named Texas Red. Although Texas Red was third behind American Pharoah when the two met in the FrontRunner Stakes, Texas Red would win the Breeders' Cup Juvenile when American Pharoah was withdrawn due to injury. It was Keith's first Breeders' Cup win and Kent's fifth, and the first time brothers had combined to win a Breeders' Cup race. Unfortunately, Texas Red missed most of the 2015 racing season due to injury. When he finally did get his second chance at American Pharoah in the Travers Stakes, they both lost to Keen Ice, a colt that had previously been Desormeaux's mount. The brothers next teamed up with another colt, Exaggerator. After an encouraging two-year-old campaign in 2015, Desormeaux rode the colt to an impressive come-from-behind victory in the 2016 Santa Anita Derby that made the colt the second betting choice for the 2016 Kentucky Derby.