Dan TreacyWed, April 29, 2026 at 8:08 PM UTC·6 min readBob 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.
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. Silver Charm would go on to win the Preakness as well, but his Triple Crown chase ended with a second-place finish in the Belmont Stakes.
The win came in Baffert's second Kentucky Derby appearance, and it marked his first win in an American Classic race.
Baffert went back-to-back with Kentucky Derby wins when Real Quiet won in 1998. The derby also marked the first career win for jockey Kent Desormeaux, who would go on to win two more times.
Real Quiet finished the race in 2:02.38, edging out Victory Gallop, and he also won the Preakness Stakes before finishing second at the Belmont Stakes and narrowly missing the Triple Crown.
Baffert won his third Kentucky Derby with War Emblem, who won by four lengths over Proud Citizen. War Emblem was jockeyed by Victor Espinoza, who went on to win the Derby two more times.
Baffert only started training War Emblem about one month before the race and said a Kentucky Derby win would make it "the best and shortest training job ever." Despite fairly distant odds, War Emblem won comfortably.
War Emblem gave Baffert a third try at the Triple Crown after winning the Preakness Stakes, but he didn't come as close in the Belmont as Silver Charm or Real Quiet, instead finishing eighth.
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Baffert finally got his Triple Crown in 2015, and it started at the Kentucky Derby with a win from American Pharoah. Baffert's first Kentucky Derby win in 13 years came via the same jockey who won in 2002 — Victor Espinoza — and pre-race favorite American Pharoah prevailed over Firing Line by one length to start what would be a journey to the first Triple Crown by any horse since 1978.
Justify was likewise no Cinderella Story at Churchill Downs, as he entered as the odds-on favorite and won by two-and-a-half lengths to give Baffert his fifth Kentucky Derby win. Mike Smith became the fourth jockey to win the Derby with a horse trained by Baffert, picking up his second win in the iconic race.
Justify went on to win the Triple Crown, matching American Pharoah's dominance and giving Baffert two Triple Crowns in four years after no one had won in 37 years.
A year before Medina Spirit won and was subsequently disqualified, Baffert tied the all-time record with his sixth Kentucky Derby win. Authentic upset the heavily favored Tiz the Law in an unprecedented September race, which was moved due to the COVID-19 pandemic.
The postponement changed the order of the Triple Crown races, as the Belmont Stakes was run in June. Authentic wasn't in that field, so this Kentucky Derby win didn't give Baffert a chance at a third Triple Crown. It did, however, deny Tiz the Law what many believed was a legitimate chance to win all three races.
Baffert is tied for the most Kentucky Derby wins of any trainer with six, matching Ben Jones' mark of six. Baffert is the only trainer to win the Kentucky Derby at least three times in the 21st century.