It started out lucky, then it stumbled and had no chance. Then, out of the blue, a regional horse race in May, run with ordinary horses and staged a really long way from the big-money stables, suddenly became the most important horse race in America.
How do you explain that?
And while we're at it, how did that race become even bigger than a horse race? How did it get to be an event that is not just a horse race but a spring rite, an American holiday and a party excuse?
Was it money? Luck? Geography? Hype? A confluence of stupid choices by some men and smart ones by others? Was it destiny?
A heap of yesses and a maybe.
Mostly, though, it was a man with the improbably promising name of Winn, who rode in on a horse named Regret.
In the beginning
The first time it was run, the Kentucky Derby wasn't even the main event at the track that day. But if beginner's luck means anything, it had that.
On May 17 in 1875, a Monday afternoon, Kentucky Derby winner Aristides ran the then-11/2-mile race in 2:373/4, a world-record time for a 3-year-old. The New York Sun noted the next day that Louisville's inaugural event was "extraordinarily successful." Of course, it didn't turn a profit for 29 years, and that feat was accomplished by a man who was in the infield on that first Derby day, standing in the seat of his father's grocery truck so he could see: 14-year-old Martin Joseph Winn.
For the first quarter-century of the Derby, Churchill Downs was run by Col. Lewis Clark, who built the track to face the afternoon sun; who thought sportswriters shouldn't bet on races; and who, in 1886, banned bookmakers, which so angered owners such as James Ben Ali Haggin, owner of the great Ben Ali, that they took to boycotting the track.
These were not Derby builders. In 1902, desperate to keep the track alive, a group of investors approached Winn, now called Matt, to buy in. Winn set about offering his friends good seats to the 1903 Derby, then offered them memberships at $200 apiece to an exclusive clubhouse at the Downs. He simultaneously placed ads in the New York papers extolling the Kentucky Derby as the greatest race ever run.
"What he had that no one before him did," says Andrew Plattner, author of The Kentucky Derby Vault: A History of the Run for the Roses, "was, he really understood what the Derby could be."
Winn was a dreamer, but he also was pragmatic. He promptly turned the grandstands around. He became a partner with the Empire City Race Track in Yonkers, outside of New York City. It was his calculated move to get closer to the Eastern racing establishment, and it helped him become close with all the New York sportswriters. When May rolled around, he paid all the sportswriters' expenses to Louisville so they feel the river breeze and drink the commonwealth's bourbon.
The sportswriters, duly impressed, drunk or paid well, did their part.
'It's the horses'
The city of Louisville almost ruined the whole thing by passing anti-gambling legislation just before Derby Day 1908. Winn, one step ahead of everyone else, managed to hold off enforcement of the law until after the Derby. Then he got the courts to take a closer look, only to find that parimutuel betting was excluded.
In 1910, Winn opened the infield to free admittance, bumping attendance to 40,000.
In 1911, when the state of New York outlawed wagering at its racetracks, Winn lowered the minimum bet at Churchill from $5 to $2.
In later years, Winn would be credited with all kinds of innovations that appealed to a radio and TV generation: the tradition of hats and finery, the emotional singing of My Old Kentucky Home, the silver julep cups sprigged with fresh mint, the thick and rich blanket of hundreds of roses hanging on the slick neck of the newest horse immortal.
That's all well and good, says Allan Carter, historian for the National Museum of Racing and Hall of Fame in Saratoga Springs, N.Y. But "it's the horses" that made the Derby the Derby, and it was the horses' stories that kept the public's attention until it was.
In 1913, 91-1 shot Donerail paid $184.90 for a $2 ticket, the biggest payout for a Derby winner ever or since. In 1914, the finest Thoroughbred of his day, Lexington-bred Old Rosebud, the top 2-year-old the year before with bloodlines back to Eclipse, did Winn a favor by winning by 8 lengths. For the first time, real horsemen sat up and took notice.
Then came 1915, the year that Winn persuaded multi millionaire New Yorker Harry Payne Whitney, a man with Lexington ties, to bring his unbeaten filly, Regret, to the race. Trained by James Rowe, a man who had 34 previous champions, Regret was out of a daughter of Hamburg by Broomstick. She'd won three races in 14 straight days at Saratoga, yet there were plenty of owners of colts who thought they could beat her in Kentucky.
They were wrong.
"I do not care if she never wins another race, or if she never starts in another race," Whitney told reporters. "She has won the greatest race in America, and I am satisfied."
"Behind Regret trailed the greatest field that had ever worn silk in this premier turf event," one reporter wrote.
Many who tell the story of the Derby point to that race as the moment that the Derby evolved because men of wealth and importance were set on a course to go after it, Plattner says.
"The object of their desires are, for better or worse, taken on by the rest of us as significant."
It is the American way.
Second to baseball
The horses started coming and, although not all were great, they tended to come with great stories. In 1918, Exterminator, a horse whose owner needed convincing to let him run, took the race and went on to be one of the century's greatest racehorses. A horse named Black Gold won the Derby in 1924, a race foreseen in a dream by his poor Native American owner, whose subsequent oil strike allowed his widow to buy the horse.
Proof that the Derby had not quite made its mark can be found in one man's decision not to bother his horse with the race in 1920. Samuel Riddle thought it was too early to bring Man o' War from Lexington to Louisville for the race. The magnificent Thoroughbred, considered by many the best of the century, went on to win the Belmont and the Preakness that year.
In 1925, when horse racing was second only to baseball in national popularity, Louisville radio station WHAS aired the first Derby broadcast across the country. With 5.5 million people listening, New York Journal-American writer Bill Corum called it, for the first time, "the run for the roses."
It's a measure of the growth of the Derby that in just 12 years, even the unimpressible were awed.
Whitney, upon winning his second Derby in 1927 with Whiskery, noted that the stands held 80,000 people. He was heard to ask above the din: "Are there always this many people here?"
'It's our day'
Since Winn took over, the previously unprofitable Churchill Downs had never lost money.
But that is business. What of his ability to move the racetrack's most popular race from mere horse race to American event?
Author Plattner says the first real step in that direction came in the 1930s and '40s, when Gallant Fox, War Admiral, Whirlaway and Citation raced, that the Derby started to go "on autopilot." That is, the racing world relented and acknowledged the Derby's supremacy. And all of the 40-plus races for 3-year-olds preceding the Kentucky Derby are now known simply as Derby prep races. It's also when Winn had celebrities flocking to this race. There was Babe Ruth, Knute Rockne, the Duke and Duchess of Windsor, John Wayne, Irene Dunne, Don Ameche, Bob Hope and Jerry Lewis.
Even presidents started to show up.
Still, in the end, with all Winn did, says Katherine Veitschegger, curator of collections at the Kentucky Derby Museum, no one can take away the one-day wonder of blue-skied-state-pride that works in person and on television.
"It looks as good on TV as it does when you're here," Veitschegger says. "It's our day. The horses just gleam. The roses, the hats, the track, it's seductive."
Longtime Atlanta Journal-Constitution sportswriter Furman Bisher will give you that. His 96-year-old sister just bought a new flat-screen TV so he can watch it this year and feel as if he's there. But he has seen 60 Derbys in person. His first was in 1960. His last was in 2007. He is 92.
Bisher says the Derby became the Derby because it's in Kentucky, with all its tradition.
You watch the Masters golf tournament in Augusta, Ga., for that reason. Ditto for the great car race in Indianapolis.
For America's greatest horse race, you go to "Kentucky, the heartbeat of the Thoroughbred industry, because no other race comes close in terms of quality and tradition."
The question posed, it seems, is now circuitous, and answers itself.