LOUISVILLE — With the Kentucky Derby just a couple of days away, it is worth revisiting the word “upset.” it is worth revisiting because just yesterday I heard someone here in Louisville repeat the myth of how the word “upset” actually goes back to a horse named Upset, a thoroughbred who on a magical day in 1919 beat the great Man o’ War. This is a stubborn legend, one that sounds too good and too sensible not to be true. Unfortunately, it’s not true, it’s not close to being true, and while the story is harmless enough, I think often of the line in the underrated movie Avalon: “Jules,” the old man said, “if you stop remembering you forget.”
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Many people still believe that Man o’ War was the greatest American racehorse of them all, greater even than Secretariat or Seattle Slew or Affirmed or any of the other great horses that followed. Man o’ War won 20 of the 21 races he entered. He did not win the Kentucky Derby because his owner, Samuel D. Riddle., did not enter him. Why not? Some say it’s because he didn’t like racing in Kentucky. Some say he did not think Man o’ War was ready for the distance. Some say that because nobody called the Kentucky Derby-Preakness-Belmont series the “Triple Crown,” it simply wasn’t a big deal to skip the Derby.
Nobody knows for sure. But believe it or not, the word “riddle” does not go back to Riddle’s decision.
Riddle did enter Man O’ War in the Preakness, and the thoroughbred set a track record. He did enter Man o’ War in the Belmont Stakes and the thoroughbred won by 20 lengths. Man o’ War also won the Withers, the Dwyer, the Miller …
Man o’ War was so dominant that — and if you want a nice legendary story, choose this one because it is true — nobody even wanted to enter their horse against him. Man O’ War was entered into the Lawrence Realization Stakes at Belmont in September of 1920. A few weeks before the race, there was a pleading article in the New York Times that seemed to be BEGGING other owners to enter their thoroughbred into the race. “It is expected to attract 10 or or a dozen of the greatest three year old colts and fillies,” the Times reported hopefully, and then listed off a bunch of them (“Five or six of the best of these brilliant colts would make a field worthy of the best traditions of the Realization,” the report continued in desperation).
Well, the Lawrence Realization Stakes didn’t get 10 or 12 horses. It didn’t get five or six. Exactly one challenger — the excellently named Sea Mint — entered into the race. And to no one’s surprise, shortly before the race, Sea Mint scratched. It looked like Man o’ War would win in a walkover and the race would not even be run.
Then, something rather extraordinary happened. Samuel Riddle’s niece, Sarah Jeffords, entered a horse called Hoodwink just so the race would be run. Well, that was not the extraordinary part. Hoodwink was so unexceptional a horse that even the Times’ beseeching story did not name him among the possible contenders. Man o’ War went off at 1-100 odds. No, that’s right, 1-100. You had to bet $100 on Man o’ War to win $1. The New York Times reported that there were some bets made on Man ‘o War — probably just for souvenir purposes — but there were also at least a couple of bets made on Hoodwink, proving that some people simply cannot resist a long shot. (“On the other hand,” the TImes correspondent wrote, “a few wagers were made on Hoodwink, perhaps with the thought that Man o’ War might jump over the fence or break a few legs”).
No, the extraordinary part was that Man o’ War put on a one-horse show for the ages. In front of a large crowd, the two horses started relatively close and were close for the first furlong. Then Man o’ War took off. With no competition — running just for the crowd and the joy of speed — Man o’ War ran faster than any horse ever timed. He did not just break the world record for a mile and five furlongs (roughly 1.6 miles), he shattered it by almost two seconds. And, as numerous people pointed out, he broke the record carrying a rather staggering 126 pounds. War Mint, who had set the record a decade earlier, was carrying only 78. Man o’ War was so dominant that day, reporters literally did not know how to calculate his margin of victory. Some reporters calculated him winning by 100 lengths. Others said it was a quarter-of-a-mile.
The Times writer put it most poetically: “He got so far ahead of Hoodwinked after the first 100 yards that no comparison could be made.”
So, that was the dominance of Man O’ War — which is why the Upset Story seems so plausible that is just HAS to be true. In 1919, at the Sanford Memorial in Saratoga Springs, Man O’ War was beaten by a half-length by Upset. That’s the part everyone seems to know. But there are things people miss.
One, the sports term “Upset” was so common in sports and horse racing, that the Washington Post reporter after the Sanford Memorial felt it necessary to write in his first paragraph, “One might make all sorts of puns about it being an upset.”
Two, it was not an especially big or compelling upset. Yes, Man O’ War went off as a 1-2 favorite, but he was still a two-year-old colt, still more promise than legend. There was still an argument then whether Man o’ War or another thoroughbred named Golden Broom was the best of the class. Upset, despite his name, was a good horse and the third choice.
Even more to the point, though, was that nobody who was at the event was shocked after the race that Man o’ War lost. Instead, people were shocked that Man o’ War made it as close as he did. In 1919 — and for more than a decade after — there were no starting gates at horse races. Because of this, starts could be nightmares, and this one was for Man o’ War. The usual starter, Mars Cassidy (grandfather of longtime New York Racing Association announcer by the same name) was sick. So he was replaced by a Charles Pettingill, who apparently had been a great starter in his younger days. Unfortunately, it was his MUCH younger days, and it is fair to say that he sort of seemed past his prime.
Again, there are different accounts — everyone seems to agree that before the start, Man o’ War was ready to roll, and he broke early more than once. Pettingill warned jockey Johnny Loftus that he would disqualify Man o’ War. Because of this,Loftus circled his horse around and while circling it, the race began. How bad was the start? One account had him a length and a half BEHIND the starting line when the race began. Another had him facing almost entirely the wrong way. Another more sinister account had Loftus starting poorly on purpose, a nasty and baseless little charge that almost 50 years later Loftus was still fighting.
“I’ve explained that race hundreds of times,” Loftus told Sports Illustrated. “I was the goat. That’s all there was to it. It could happen to anyone. … Heck, if a ballplayer makes an error, it’s forgotten. Why can’t they forget that race?”
The bad start was only part of the problem for Man o’ War. He also was held by by a poor strategy devised by the owner to stay back through the early part of the race. This meant that Man o’ War got blocked on more than one occasion. In the backstretch, Man o’ War took off and gained ground on the leaders, Upset and Golden Broom. He gained so fast on Golden Broom, in fact, that he almost ran into the back of the horse. “I had to check Man o’ War and go to the outside,” Loftus said. “It cost me the race.”
Sadly, after Man o’ War destroyed Upset in the Grand Union Hotel Stakes just three weeks later, there were rumors that Loftus had thrown the race — rumors that would haunt him for the rest of his life. One year later, he was not granted a riding license, and though no official reason was ever given, he and everyone else knew why. Willie Knapp, who was on Upset that day (and also would have his license pulled), would say that Loftus would not have taken even $100,000 to throw that race. He had run into bad racing luck. And it happens.
“Any other day,” Knapp told reporters, “he’d have beaten me carrying a piano.”
In any case, the Upset victory was not the beginning of the phrase “upset victory.” Not at all. The phrase had been around for probably 50 years, and it was so mainstream by the late 1910s that, well, a horseman named Henry Payne Whitney was searching for a name of a new colt by Whiskbroom II and Pankhurst. He could not help but think this horse might surprise a few people in the years ahead. And so, he named the horse “Upset.”