Bob Baffert Kentucky Derby wins timeline: How controversial trainer can make history at 2026 race

Bob Baffert Kentucky Derby wins timeline: How controversial trainer can make history at 2026 race originally appeared on The Sporting News . Add The Sporting News as a Preferred Source by clicking here . The path to a Kentucky Derby win is monumentally difficult under any circumstances, but the presence of legendary trainer Bob Baffert adds one more major challenge for the rest of the field in 2026.

Baffert became eligible to enter horses again in 2025 after a suspension kept him out of the Kentucky Derby for three consecutive years. While he didn't win in his return, Baffert remains one win away from becoming the winningest trainer in the iconic race's history. Baffert already held that title — only briefly.

The disqualification of Medina Spirit in 2021 temporarily derailed Baffert's career, but with Potente and Litmus Test in the field in 2026, he's hoping to claim what he believes is rightfully his. Here's a look back at Baffert's Kentucky Derby wins and how many Triple Crowns he has won. MORE: What to know about Churchill Downs Bob Baffert Kentucky Derby wins Silver Charm, 1997 A younger Baffert picked up his first Kentucky Derby win with Silver Charm in 1997.

Silver Charm was jockeyed by Gary Stevens, who previously won the Kentucky Derby in 1988 and 1995. Finishing with a time of 2:02. 44, Silver Charm took the lead over Captain Bodgit right near the end.