Ranking the 10 Most Memorable Races in Kentucky Derby History

Brendan O'Meara@@BrendanOMearaFeatured ColumnistApril 29, 2014

Ranking the 10 Most Memorable Races in Kentucky Derby History

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    A statue of the great Secretariat is a prominent feature at Belmont Park. He ran the fastest Kentucky Derby in the race's history.
    A statue of the great Secretariat is a prominent feature at Belmont Park. He ran the fastest Kentucky Derby in the race's history.CHARLES KRUPA

    Come Saturday there will 140 runnings of the Kentucky Derby. That's 140 immortal horses. Every race is different. There's simply no way to tell how it will unfold from year to year. Each new running brings a new crop of horses with their own styles and personalities. The weather in Louisville can be 85 degrees and dry as gin, or it can be 55 degrees and raining so hard you'll want to wrangle up animals two by two.

    Over the 139 previous runnings of the Derby, a few stand out. The criteria for the following races may be with the extenuating story as in Brokers Tip in 1933, Forward Pass from 1968 and Affirmed in 1978. Others were chosen based on the pure physicality of the athlete and the performance at hand. 

    Picking 10 races was tough because this race is so iconic, special and diverse, but the following list aims to illustrate the cream of an amazing crop. Read on and let the debating commence.

10. Brokers Tip, 1933

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    The early Derbies are hard to quantify, but that's not the case with 59th running of the Kentucky Derby. Brokers Tip, the eventual winner, comes up the rail to challenge Head Play. The battle the horses underwent played second fiddle to the jockeys in this race.

    Don Meade, aboard Brokers Tip, and Herb Fisher, riding Head Play, tangle with each other by grabbing arms and whips. It's amazing they remained in the saddle. They were promptly removed from the saddle for 30 days following their tussle, but it was their war down the homestretch that made this renewal of the Kentucky Derby a most memorable race.

9. Lawrin, 1938

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    Lawrin's win in the 64th Kentucky Derby wasn't a memorable run per se but memorable in that it was Eddie Arcaro's first Derby win. Arcaro is tied with Bill Hartack for the most Derby wins by a jockey with five.

    Arcaro went on to win the most Triple Crown races of any jockey and remains the only jockey to win the Triple Crown twice, a record that will never be broken. Those horses were Whirlaway in 1941 and Citation in 1948.

    It was Lawrin's win, like Michael Jordan's winning jumper in the 1982 NCAA final, that ignited a clutch career of big wins for Arcaro, culminating with a plaque in the Hall of Fame.

8. Forward Pass, 1968

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    Dancer's Image is the only horse to have been disqualified after winning the Kentucky Derby.
    Dancer's Image is the only horse to have been disqualified after winning the Kentucky Derby.Anonymous

    The commemorative Kentucky Derby mint julep glasses show Forward Pass as the 1968 Kentucky Derby winner, but he actually didn't physically win the race. He finished second to Dancer's Image, who clearly was the best horse in the race.

    When Dancer's Image was drug tested after the race, officials found traces of phenylbutazone in his urine—a banned substance at Churchill Downs at the time—and he was disqualified and placed to 14th, dead last in the field.

    He remains the only Kentucky Derby winner to be disqualified. As a result, Forward Pass became the official winner of the Derby in 1968.

7. Sea Hero, 1993

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    For those in sports who answer to a higher power, there's Sea Hero. The Derby often goes to the luckiest horse, and Sea Hero benefited from just a superb amount of racing luck.

    Prarie Bayou was the heavy favorite at 4-1 when the sea (pardon the pun) parted for Sea Hero. Just a few lengths back, a path opened up for Sea Hero and his jockey Jerry Bailey. They rode that path to the fence and hit the wire first.

    Sea Hero hadn't won a race in six months, so Bailey suggested that Sea Hero lose the blinkers—equipment that blocks the peripheral vision of a horse—for the biggest race of his career. It worked. Bailey told the Los Angeles Times:

    He was wearing blinkers in the beginning because he was green. But then with the blinkers on, he was getting too aggressive too early. The idea (about removing the blinkers) was to get him to relax. If you're getting ready to run a mile and a quarter, you don't want to have a horse who's fighting you.

    That, coupled with some racing luck, drove them home.

6. Monarchos, 2001

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    One word describes this renewal: fast. Vin Diesel would approve.

    A record half-mile fraction was set in 44.86 seconds, so anyone watching knew the final time might be something special.

    All eyes were on Point Given (who would lose the Derby, but win the Preakness and Belmont), but it was Monarchos who came charging down the center of the track. When he hit the wire, racecaller Tom Durkin said it best, "And the final time was 1:59 and 4/5 seconds! He was as fast as Secretariat!"

    Monarchos is the only other horse, besides Secretariat, to run a sub 2:00 Derby.

5. Affirmed, 1978

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    The Affirmed story has a lot of layers. Steve Cauthen, Affirmed's jockey, was the youngest ever to win the race at the age of 18.

    This was also another chapter in the long, brutal rivalry between Affirmed and Alydar. Alydar was runner-up to Affirmed in the Derby, then the Preakness, then the Belmont.

    Their rivalry dated back to their two-year-old season. In the end, Affirmed bested Alydar more than not, but their Kentucky Derby sparked an unprecedented battle that lasted through the entire Triple Crown. Their connection continued late into their lives as stallions. Shane Ryan of Grantland writes:

    Ironically, (Alydar’s) old rival, Affirmed, was also at Calumet in 1990, leased by the farm to be one of its stallions. When the two chestnut-colored horses were out in their paddocks, they would stare at each another, their manes flicking in the breeze. Occasionally, Affirmed would start running on his side of the fence, and Alydar would take off after him on the other side. Even then, twelve years after their races, they remained competitors.

    The Derby was just a brick in the wall in racing's greatest rivalry.

4. The Three Fillies, 1915, 1980, 1988

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    Saturday will mark the 140th running of the Kentucky Derby. In all that time only three, count 'em, three fillies have won the Derby. 

    Fillies, by rule, are a few lengths slower than their male counterparts. Colts tend to be bigger, stronger and faster, but occasionally along comes a filly that is every bit as fast. Regret was the first filly to beat the boys in 1915 during The War to End All Wars that subsequently didn't end war at all.

    It took 65 years for another filly to rise up, this one Genuine Risk, and smoke the boys. Eight years later, Winning Colors did it

    When the girls take on the boys, it galvanizes the public. The filly represents something greater than the race. She transcends the race and becomes a symbol for those who wish to defy convention. And sometimes, that filly wins. 

3. Mine That Bird, 2009

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    It's not only that Mine That Bird was the second-longest price in the history that ranks his Kentucky Derby win so high, it's the fearless ride Calvin Borel executed that vaults the performance up the list.

    Check this out, and you'll agree. You've heard of race car drivers trading paint. In this you'll see Borel rub some of his boot polish on the fence as he slips past Join In The Dance. The best part? Tom Durkin, the race caller, completely misses Mine That Bird. He stumbles over his usually loquacious linguistics and has to re-gather his composure. He was as shocked as everybody that day.

    Mine That Bird never won another race, but this performance is still talked about. There was even a movie inspired by his run. America loves a long shot, and there may be no shot longer than Mine That Bird to ever win the Kentucky Derby again.

2. Secretariat, 1973

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    Secretariat is considered the greatest racehorse of all time. As told by William Nack in his wonderful book Secretariat, Secretariat's breeding rights were sold in his two-year-old year based on the pretense that he would win the Triple Crown.

    Say what?

    It had been 25 years since a horse had won the Triple Crown. The year was 1948, and the horse was Citation. Triple Crowns weren't exactly the type of accomplishments a breeder could sell. They just didn't happen, only eight times prior to Big Red.

    Secretariat's Derby doesn't look particularly stunning, but his final running time, 1:59.40, is the fastest in 139 races. He drew away from Sham, the unluckiest horse having been born the same year as Secretariat. Sham's second-place effort would have broken the previous Derby time record.  

    For many who focus solely on the clock, Secretariat's Derby is No. 1. But there's one final horse who did something every bit as impressive.

1. Big Brown, 2008

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    Big Brown is the only horse to break from Post 20 (in the modern starting-gate era) and win the Derby. Post 20 is the far outside of the auxiliary gate. By breaking from the far outside, Big Brown and jockey Kent Desormeaux had to clear the entire field to save ground.

    Big Brown ran a giant quarter-mile diagonal to the clubhouse turn and was only five-wide heading into the turn. Post 20 is usually a death knell for any horse forced to break from there, but Rick Dutrow, Big Brown's trainer, liked the draw. At the time, Dutrow had his choice of 1, 2, 18, 19 and 20. Dutrow went with 20

    If we took 18 or 19, maybe he doesn't break so good and horses come over on him. Outside, he can get away clean. We felt like we took our best shot. He should be able to pop right out there and get a good position.

    That's exactly what happened. Big Brown angled in beautifully and coasted along until the 3/8ths pole when Desormeaux let Big Brown loose where he kicked clear to win by five lengths.


    Follow Brendan O'Meara on Twitter @BrendanOMeara.