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Ranking the Kentucky Derby's Most Unlikely Winners of All Time

Brendan O'MearaFeatured Columnist IIIJanuary 13, 2017

Ranking the Kentucky Derby's Most Unlikely Winners of All Time

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    It could be as easy as looking at the longest shots of all time, ranking them in order and calling it a day.

    Their odds give you an idea of how unlikely the betting public thought they’d perform. Again, a solid indicator.

    In all of the cases, the odds are longer than the line at the DMV, but I’m going to lean on some horses whose odds might not be as long, but had absolutely no business winning the Derby.

    These horses will certainly give you something to think about before post time on Saturday. Louisville in early May can be 80 degrees and sunny one second, then 60 degrees with torrential rain 20 minutes later.

    All of which can be a recipe for an unlikely winner.

Mine That Bird: Even the Race Caller Missed Him

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    Tom Durkin is the best race caller in the business and not even he saw Calvin Borel slip Mine That Bird through on the fence.

    The track that day back in 2009 was sticky and muddy. Many of the big, brawny horses with regal bloodlines sunk into the track. Mine That Bird was like Rocky, a tight, tiny ball of muscle, and he skipped over the mud like a bug on water.

    He went off at odds of 50-1 and trailed the entire field by 20 lengths heading into the clubhouse turn. Durkin missed him twice, actually. Mine That Bird was so far back after the clubhouse turn that Durkin neglected to call him. Then, as Durkin’s trained his glasses on the favorites dueling it out, Mine That Bird squeezed through on the rail to win by 6 ¾ lengths.

    Though he’d lose a gutsy race to Rachel Alexandra in the Preakness two weeks later (thus validating that he was a decent little horse), he never won another race, making him the most unlikely winner of the Derby.

Donerail: The Longest Shot of Them All

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    Donerail won the Kentucky Derby in 1913 at odds of 91-1 with jockey Roscoe Goose in the irons. Perhaps the race recap shows sums it up best from the Kentucky Derby's website:

    DONERAIL, showing startling improvement over his Lexington form, was restrained to the stretch turn, where he moved up with a rush, and, under punishment, drew away in the last sixteenth.

    Any time you show “startling improvement,” that’s every bit the reflection of a horse who had no business winning. Also, there were only seven horses in the entire field. Seven horses make it a lot easier on the favorites. There are less moving parts, less can go wrong.

    With 20-horse fields, there’s so much chaos that luck becomes the favorite, even over the field.

    So 91-1 in a seven-horse field, that’s about as unlikely as they come. And unlike Mine That Bird, he went on to win again later in his career.

Giacomo: The Pace Melteth Down

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    The day was hot and the pace was hotter. There to lap up the tiring front-runners was Giacomo storming down the middle of the track.

    What made it all the more unlikely was that a Bellamy Road was in this field. Bellamy Road, owned by George Steinbrenner, had won the Wood Memorial four weeks earlier by 17 1/2 lengths. He was so dominant that the Derby was practically handed to him. Well, if not him, then his trainer, Nick Zito.

    Zito saddled five Derby starters in the 2005—25 percent of the entire field. With numbers like that in a trainer’s favor, it’s amazing he didn’t even hit the board. Bellamy Road finished sixth.

    To give you an idea of how badly the pace melted down, Giacomo won at 50-1 and Closing Argument got up for second at 72-1. That’s an exacta (first and second place) that paid $9,814.80.

    Honey, Taco Bell's on me.

Gallahadion: "A Great Horse and a Smart Jockey"

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    Gallahadion won the Kentucky Derby in 1940 at odds of 35-1, an unlikely winner in an eight-horse field.

    I like looking at the year. 1940, Hitler was starting his blitz across Europe and the Japanese were, no doubt, planning an attack in little over a year’s time on Pearl Harbor. But watching Gallahadion march around that Churchill Downs oval while the rest of the world readied for a blood bath was about as good as it got for some time.

    Gallahadion's odds were long, but it was who Gallahadion defeated that makes his win so impressive. Bemelech was the heavy, heavy favorite who then went on to win the Preakness and Belmont Stakes. Gallahadion won six races in his 36-race career, including the San Vicente Handicap, so he wasn’t a one-shot wonder.

    His sire was Sir Gallahad, which never ceases to conjure fond memories of watching Monty Python and The Quest for the Holy Grail.

Charismatic: Held on for Dear Life

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    Charismatic was D. Wayne Lukas’s fourth career Derby win and one of the longest shots on the board at 31-1.

    Charismatic got a beautiful trip and beautiful ride from Chris Antley. Charismatic would go on to win the Preakness Stakes and had a shot at winning the Triple Crown at Belmont Park on June's first Saturday.

    He finished a gallant third in the Belmont while breaking his leg shortly before the wire. Antley quickly dismounted and cradled the broken leg, which many think saved Charismatic’s life.

    He would never have had a shot the Triple Crown were it not for his shocking Kentucky Derby, and he would never have had a shot a decent retirement were it not for Antley’s quick thinking and first aid in the clubhouse turn at Belmont Park.

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