Sierra Leone rallied from last to overtake Just A Touch down the stretch and win the $1 million Blue Grass Stakes by 1 1/2 lengths at Keeneland.
With Tyler Gaffalione aboard, Sierra Leone covered 1 1/8 miles in 1:50.08 and paid $5.32 to win.
The 8-5 favorite, one of three Chad Brown-trained entries in the 10-horse field, overcame several challenges.
Sierra Leone didn't want to enter the starting gate and after multiple attempts went into the No. 10 hole. He lagged behind for much of the race as 15-1 long shot Top Conor, another Brown pupil, and Just A Touch set the pace.
Brown said Gaffalione told him the colt got stirred up being in the far outside post next to the large crowd.
"He's still polishing off his experience and his skills," Brown said. "I just think a mile-and-a-quarter (in the Kentucky Derby) won't be a problem going forward. We're looking forward to it."
The bay colt surged through the final turn to catch the leaders and earn 100 points on the Kentucky Derby leaderboard. Epic Ride was third.