Chad Brown has won the Eclipse Award as the nation's most Outstanding Trainer four times, and his horses have won more than 2,600 races in his career. But he has never won the Kentucky Derby. He arguably will have his best shot ever at the blanket of roses on Saturday with the late-running Sierra Leone, who has been a star since the moment he hit the ground.

2 Sierra Leone (3-1)

• Trainer Chad Brown
• Jockey Tyler Gaffalione
• Last race First in the Blue Grass Stakes by 1½ lengths
• Career record 4 starts: 3 wins, 1 second
• Career earnings $918,000
• Best career Beyer Speed Figure 98 (2024 Blue Grass Stakes)
• Sire Gun Runner

Below, we'll dig further into Sierra Leone as part of our series profiling all the horses competing in the 150th Kentucky Derby on Saturday, May 4. We'll look back into his past performances, what questions need to be answered on Saturday and analyze how the post draw affects his chances.

Kentucky Derby profiles: 1 Dornoch | 2 Sierra Leone | 3 Mystik Dan | 4 Catching Freedom | 5 Catalytic | 6 Just Steel | 7 Honor Marie | 8 Just a Touch | 9 Encino | 10 T O Password | 11 Forever Young | 12 Track Phantom | 13 West Saratoga | 14 Endlessly | 15 Domestic Product | 16 Grand Mo the First | 17 Fierceness | 18 Stronghold | 19 Resilience | 20 Society Man | 21 Epic Ride

Kentucky Derby picks: Michelle Yu | Bob Weir | Jody Demling | Exotics

So what key information could decide how Sierra Leone performs in the Kentucky Derby? And how does the post draw affect his chances? ... Join SportsLine now to get a full profile on Sierra Leone and every other horse in the Kentucky Derby!