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Home / Breeders Cup / Iconic Breeders’ Cup Classic Winners: Legends of the Dirt

Iconic Breeders’ Cup Classic Winners: Legends of the Dirt

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The Breeders’ Cup Classic, often hailed as the richest and most prestigious race in Thoroughbred racing, has crowned some of the sport’s most unforgettable champions since its inception in 1984. With a $7 million purse in 2025 and a history of dramatic finishes, international intrigue, and barrier-breaking performances, the Classic has produced icons that transcend the track. Drawing from expert rankings and historical highlights, here are ten of the most iconic winners, selected for their thrilling races, cultural impact, and lasting legacy.

  1. Ferdinand (1987)
    Jockey: Bill Shoemaker | Trainer: Charlie Whittingham
    In the inaugural Classic’s most heart-pounding photo finish at Hollywood Park, the 1986 Kentucky Derby winner edged out 1987 Derby hero Alysheba in a dead-heat duel that had the crowd roaring. Shoemaker’s masterful urging turned a formful field into racing folklore, marking the race’s explosive debut.
  2. Cigar (1995)
    Jockey: Jerry Bailey | Trainer: Bill Mott
    Undefeated in 10 straight starts, Cigar unleashed a sweeping, sustained rally on a sloppy Belmont track to claim Horse of the Year honors. Bailey’s tactical hold-and-explode ride against a star-studded field, including Tinners Way, delivered one of the most powerful performances in Classic history.
  3. Zenyatta (2009)
    Jockey: Mike Smith | Trainer: John Shirreffs
    The only filly to conquer the boys, Zenyatta extended her perfect record to 14-for-14 with a jaw-dropping, 20-horse-length surge in the stretch at Santa Anita. Her rhythmic, crowd-pleasing style and barrier-shattering win captured global hearts, though her heartbreaking 2010 defeat added to the legend.
  4. Sunday Silence (1989)
    Jockey: Pat Valenzuela | Trainer: Charlie Whittingham
    Avenging his Belmont Stakes loss to rival Easy Goer, Sunday Silence nosed out the East Coast star in a rivalry-fueled thriller at Gulfstream Park. The duel between these West vs. East warriors, trained by Hall of Famer Whittingham, epitomized the Classic’s epic confrontations.
  5. Alysheba (1988)
    Jockey: Chris McCarron | Trainer: Jack Van Berg
    Bouncing back from a narrow 1987 defeat, the 1987 Derby winner stormed home at Churchill Downs to become the world’s richest horse at the time. His unyielding grit in a loaded field solidified his status as a blue-blooded icon of the early Classics.
  6. Tiznow (2001)
    Jockey: Chris McCarron | Trainer: Jay Robbins
    In a post-9/11 emotional high, the 2000 winner repeated as the only horse to win back-to-back Classics, edging European invader Sakhee in a wide-open Belmont battle. McCarron’s fifth Classic triumph added a layer of Hollywood drama to this American triumph.
  7. Ghostzapper (2004)
    Jockey: Javier Castellano | Trainer: Robert Frankel
    Shocking the field with a wire-to-wire demolition at Lone Star Park, Ghostzapper earned the highest-ever Brisnet speed figure (116) while crushing Derby winner Funny Cide and repeat champ Pleasantly Perfect. His unexpected front-running dominance redefined “unbeatable.”
  8. Awesome Again (1998)
    Jockey: Pat Day | Trainer: Patrick Byrne
    In one of the deepest fields ever at Churchill Downs, Awesome Again powered through traffic to deny Silver Charm and Skip Away in a chaotic stretch run. The “MegaTron” finish, with Swain veering wildly, made this a benchmark for Classic chaos and class.
  9. Unbridled (1990)
    Jockey: Pat Day | Trainer: Carl Nafzger
    From post 14 in a 14-horse Belmont melee, the Kentucky Derby winner sliced through a shrinking hole for a rail-skimming victory. As one of just four horses to sweep the Derby and Classic in the same year, his improbable journey from wide post to wire cemented his heroic tale.
  10. Mucho Macho Man (2013)
    Jockey: Gary Stevens | Trainer: Kathy Ritvo
    The 55-1 longshot stalked the pace at Santa Anita before holding off Will Take Charge and Declaration of War in a three-horse thriller. Stevens’ comeback ride for trainer Ritvo, the first female trainer to win the Classic, turned underdog dreams into one of the most exhilarating finishes.

Beyond the Top 10: Other Timeless Standouts

While the above captures peak drama, no list is complete without modern immortals. American Pharoah (2015), ridden by Victor Espinoza and trained by Bob Baffert, achieved the first Grand Slam (Triple Crown + Classic) at Keeneland, ending a 37-year drought for U.S. racing fans. Justify (2018), under Mike Smith and Baffert, became only the second Grand Slam winner (and first undefeated), galloping to glory at Churchill Downs. Finally, Flightline (2022) demolished the field by 8¼ lengths at Keeneland, posting the fastest Classic time ever and retiring unbeaten in six starts—a performance some call the greatest in Breeders’ Cup history.

These winners not only hoisted trophies but shaped the sport, inspiring films, books, and a new generation of fans. As the 2025 Classic looms at Del Mar on November 1, who will join this pantheon?