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    By Brandon Quick
    Cover Photo by Adam Mescan

    All 142 Kentucky Derby winners are special. But not all are equal. Here’s my take on the 10 best of all time, plus eight not-so-great horses who won the roses and the five best who never made the Derby starting gate but should have.


    10. Gallant Fox (1930)
    This colt was the second horse to win the Triple Crown, a term that didn’t exist until a New York Times writer used it to coin Gallant Fox’s accomplishment. The horse further stands out among racing’s 12 Triple Crown winners because he became the only Triple Crown winner to sire a Triple Crown winner: Omaha, who swept the trio of races in 1935.

    9. Whirlaway (1941)
    Racing’s fifth Triple Crown winner, Whirlaway (great name, by the way) holds the record for margin of victory in the Kentucky Derby, obliterating the field by eight lengths. He was also nicknamed “Mr. Longtail,” which is pretty cool in its own right.

    Image: Whirlaway

    8. Count Fleet (1943) 
    They don’t make ponies like they used to, and this old war horse represents a bygone era, bouncing back to win the 1943 Triple Crown just weeks after injuring a hind leg in the Wood Memorial. The colt was shipped to Churchill by train with legendary jockey Johnny Longden holding icepacks to the afflicted limb. Count Fleet won the Derby by three lengths, the Preakness by eight and the Belmont by 25 — the second-largest margin of victory behind Secretariat’s 31. Unlike Big Red, however, Count Fleet won the Withers Stakes before the Belmont and also sired a Derby winner, 1951 hero Count Turf. 

    7. Northern Dancer (1964)
    Certainly one of the best-looking Derby horses of all time, Northern Dancer proved more than just a bay-colored Adonis. The powerful colt won 14 of 18 starts and never finished off the board, while winning the Derby in then-record time and taking the Preakness two weeks later. He would go on to become arguably the best and most influential stallion in the sport’s history, siring, grand-siring and broodmare-siring the best horses in the United States and Europe for decades. 

    6. Barbaro (2006)
    Perhaps a sentimental choice to be included this high on the list, but the horse who captured hearts around the world after his catastrophic injury in the Preakness was also a serious runner who won the Derby by six-and-a-half lengths without any urging. Barbaro finished his career undefeated in six starts and is the ultimate “what could have been?” Derby winner. The Barbaro statue outside the main gate at Churchill Downs is a fitting tribute. 

    5. American Pharoah (2015)
    Just when people were beginning to doubt whether there would be another Triple Crown winner, along came the brilliant horse with the misspelled name. The Derby, Preakness, Belmont Stakes and Breeders’ Cup Classic winner deserved better, but his legacy is firmly cemented — the Jockey Club has reserved both American Pharoah and the correctly spelled “Pharaoh” so that no future horse can bear the same name.

    Image: American Pharoah / Mike Lizzie

    4. Seattle Slew (1977)
    One of the most popular names and the best rags-to-riches story in racing history, Slew, a $17,500 purchase as a yearling, became the 10th Triple Crown winner and the only horse to accomplish the feat while undefeated. Seattle Slew is also the only Triple Crown winner to defeat another Triple Crown winner, which he did in 1978 by beating Affirmed in Belmont Park’s Marlboro Cup.

    3. Citation (1948)
    There’s a valid argument that the eighth Triple Crown winner was the best of all time, and the numbers don’t lie. “The Big Cy” raced an astounding 29 times as a three-year-old and won 27. He is one of just three Thoroughbreds to win at least 16 consecutive races at the graded-stakes level and was the first horse to eclipse $1 million in career earnings. 

    2. Spectacular Bid (1979)
    This steel-gray colt, affectionately called “the Bid,” was destined to be the fourth Triple Crown winner of the 1970s, but a poorly timed ride in the Belmont coupled with the fact the colt stepped on a safety pin the morning of the race prevented a normal effort. Still, Spectacular Bid won 26 of 30 career starts and was a champion at two, three and four years of age. 

    1. Secretariat (1973)
    No surprise here. The horse that transcended racing and inspired a Disney movie was the fastest horse in Kentucky Derby history, completing the mile and a quarter in 1:59.40. Big Red also owns the fastest times in the Preakness and Belmont Stakes — the latter a 31-length score that smashed the track record and seems sure to stand as long as the race is held. The book titled The Horse God Built pretty much sums it up.

    Image: Secretariat winning the Belmont Stakes / Charles LeBlanc



    Winning the Kentucky Derby does not automatically make you a great horse. Consider this fact among recent winners: In their 24 post-Derby starts, Giacomo (2005), Mine That Bird (2009), Super Saver (2010) and Orb (2013)had just a single win between them. Hardly the mark of greatness.

    8. Super Saver (2010)
    With just the Derby win to his credit in five starts as a three-year-old, Super Saver got a big assist from a muddy track and a patented rail-skimming trip from jockey Calvin Borel. Come to think of it, those exact same words could be said about Mine That Bird a year earlier — a true testament to the fearlessness of Cajun-born “Bo-rail.” 

    7. Giacomo (2005)
    He was really nothing more than a late-running type who benefited from a pace meltdown. Champion Afleet Alex came back to smoke Giacomo in the Preakness and Belmont, and Giacomo won just three of 16 career starts, including one for eight after the Derby. 

    Image: Giacomo

    6. Gato Del Sol (1982)
    Every dog has his day, and so, too, did the cat of the sun. This horse was a plodder who beat one of the weakest Kentucky Derby fields of the modern era. 

    5. Dust Commander (1970)
    At the 1970 Derby, Hunter S. Thompson was etching ideas for his famous essay, “The Kentucky Derby Is Decadent and Depraved,” when Dust Commander became the only horse born in Illinois to win the big one, despite a career otherwise lacking in significant accomplishments (eight wins in 42 starts). 

    4. Donerail (1913)
    The answer to a trivia question, Donerail is the biggest longshot to wear the roses, returning $184.90 on a $2 bet — and, no, you won’t find anything close to those odds this Derby Day. As for Donerail, he was not only a Derby winner, but also a patriot, finishing his days siring horses for the U.S. Army Remount Service. 

    Image: Donerail

    3. Mine That Bird (2009)
    At his best, he was pretty good, but it’s just that he wasn’t very good for very long. The second-biggest longshot to win the Derby looked much slower than his rivals on paper prior to springing the upset. He ran a respectable second in the Preakness and third in the Belmont, but his 0-for-9 record after the Derby speaks loudly. 

    2. Apollo (1882)
    It’s hard to pick on a horse born 14 years after the conclusion of the Civil War, but Apollo shows no other major wins in his 52-race career. By age five, he was a retired saddle horse for a friend of the owner’s wife. 

    1. Stone Street (1908)
    This poor guy recorded the slowest time — by far — in Kentucky Derby history at just a tick over 2:15 and never won a major race other than the Derby despite 92 career starts. The annals show the track was quite muddy on the first Saturday in May of 1908, but mathematically speaking, Stone Street would have finished almost 80 lengths behind Secretariat. 

    Image: Stone Street / Louisville Magazine



    Not all great American dirt horses run in the Derby. In fact, there’s an exhaustive list — and many recent examples — of horses with Hall of Fame credentials who never entered the Derby starting gate. 

    5.  Arrogate (Derby Eligible in 2016)
    If the ’70s proved anything, it’s that Triple Crown winners and freakish equine talent can come in bunches. Just a year removed from American Pharoah, trainer Bob Baffert certainly has another runner of similar ability in his barn, but greatness can’t be rushed. Arrogate, who is the only currently active runner on this list, was kicked in the teeth by another horse as a yearling, and while the boot to the chompers didn’t cause the horse’s slower development, he did not make his career debut until April 17 last year, finishing third in a maiden event at Los Alamitos in California. In other words, while Nyquist was winning the 2016 Derby, Arrogate was an unknown maiden. Now clearly the best of his generation, Arrogate’s meteoric rise to success includes six consecutive wins, marked by a track record in the historic Grade 1 Travers, a thrilling defeat of 2014 Derby winner California Chrome in the Breeders’ Cup Classic and an easy victory in the newly created $12 million Pegasus World Cup, where he again defeated Chrome. Well on pace to becoming the richest racehorse in Thoroughbred history, Arrogate has earned more than $11 million in seven starts and will be the heavy favorite in the March 25 Dubai World Cup worth $10 million.

    Image: Arrogate (#10) overtook California Chrome (#4) in the final yards of the race to win the Breeders' Cup Classic

    4. Zenyatta (Derby Eligible 2007)
    The Queen of Racing won 19 of 20 races, her lone loss by a head in the last start of her career, the 2010 Breeders’ Cup Classic. Zenyatta won the 2008 Breeders’ Cup Distaff and in 2009 became the first and only female to win the Breeders’ Cup Classic. 

    3. Rachel Alexandra (Derby Eligible 2009)
    Like Secretariat at the Belmont Stakes, Rachel was running only against herself while winning the 2009 Kentucky Oaks by a record 20¼ lengths. Most thought she instead should have been running in the Kentucky Derby the next day — a sentiment reinforced when she came back two weeks later to beat 2009 Derby winner Mine That Bird in the Preakness, becoming the first filly to win that race in 84 years.

    Image: Rachel Alexandra winning the 2009 Woodward Stakes / Scott Serio

    2. Ghostzapper (Derby Eligible 2003)
    Highly regarded as a sprinter, Ghostzapper, already known to be one of the fastest horses since the advent of Beyer Speed Figures, further cemented his legacy by handling the classic mile-and-a-quarter distance with a front-running destruction of the 2004 Breeders’ Cup Classic field. 

    1. Cigar (Derby Eligible 1993)
    Cigar did not race as a two-year-old and was primarily a middling turf horse at three. It wasn’t until he was switched to the dirt and the care of Hall of Fame trainer Bill Mott that the real Cigar emerged, winning 16 consecutive races at the graded-stakes level, including the 1995 Breeders’ Cup Classic. A statue in the paddock of Gulfstream Park in Florida memorializes this great champ, who lived out his retirement years at the Kentucky Horse Park until his death in 2014. 

    This originally appeared in the April 2017 issue of Louisville Magazine. To subscribe to Louisville Magazine, click here. To find your very own copy of Louisville Magazine, click here. 

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