Horse Racing Urban Legends #1

This is the first in a series of examinations of horse racing-related urban legends and whether they are true or false. This week, discover if the term “upset” came from the world of horse racing, whether a side bet unintentionally led to the first horse to win the Triple Crown and whether Secretariat was acquired by a lost coss toss.

Let’s begin!

HORSE RACING URBAN LEGEND: The term “upset” to describe an underdog winning a sporting event was derived from a horse named Upset defeating the heavily favored Man o’ War in 1919.


There are certain sports stories that are just so good that you almost feel bad debunking them. This is one of those stories.

As you are all well aware, one of the meanings of the word “upset,” especially when applied to the world of sports (although politics, or really, anything involving competitions between people, has latched on to the word, as well), is to describe situations where a favored team/athlete/horse loses to an underdog opponent.

The origin of the term is thought to have derived from one of the biggest upsets in horse racing history. Man o’ War is one of the greatest Thoroughbred racehorses history (amusingly enough, with the 2011 Kentucky Derby just being run, Man o’ War never actually competed in the Kentucky Derby, so he never had the chance to win the Triple Crown), with a 20-1 record. Blood-Horse magazine named him the #1 Racehorse of the 20th Century. And yet, on August 12, 1919, Man o’ War lost its only race ever – to a horse that it had already defeated six times before! There are plenty of places that tell how this story led to the term “upset,” so I’ll just pick literally the first result that came up for me when I did a web search. Here, from the official Secretariat website, in an article about how Secretariat also lost to a severe underdog in 1973 is a description of Man o’ War’s loss:

It was at Saratoga, in 1919, that the word “upset” entered the American sports lexicon. That’s when a horse named Upset beat the mighty Man o’ War. It was the original Big Red’s only defeat.

In those days, the word upset had a more literal meaning, along the lines of tip over, or capsize. But it had no particular connection with sports.

Then came Upset’s victory over the seemingly invincible Man o’ War. So shocking was Upset’s triumph over Man o’ War, that sports scribes began to describe unexpected outcomes in other sports like football and basketball by saying so-and-so “pulled off an Upset.” Eventually, the capitalized “U” in Upset became lower case as upset became a part of regular usage, and a word we know well today.

So, is that true?

First off, a little bit about that race itself. You see, while Man o’ War DID lose the race, it was clearly the best horse in the race that day. What happened was that there was a mix-up at the start of the race. They did not have starting gates back then – the horses were just lined up behind a barrier and then told to go. Well, the horses on that day in August 1919 were not lined up well at all. As Fred Van Ness of the New York Times described it at the time:

For those who had hoped for a pretty race without anything to mar it, it was unfortunate that the acting starter, C.H. Pettingill, one of the placing judges, spent several minutes trying to get the horses lined up and then sent them away with only those near the rail ready for the start.

So when the race began, a bunch of horses had a wide lead on Man o’ War, with Upset being the best of that bunch. However, to the astonishment of the crowd, Man o’ War was so fast that the horse nearly caught up to Upset and clearly would have overtaken the lead horse if the course was twenty or so feet longer.

Now as to the origins of the word “upset.” The first problem with the idea that Upset originated the term is the fact that if you look at the meaning of the word, the usage of “upset” to mean “an overthrowing or overturn of ideas, plans, etc.” had long in use. So just keeping that in mind, it does not exactly take a lot of stretching to get that meaning applied to the world of sports. It is not like the horse was named, say, Mailbox and suddenly people were saying “that horse pulled a mailbox” or “The Braves really mailboxed the Phillies today.” A long accepted meaning of the word was quite similar to its usage in relation to sports.

However, the main evidence that the term did not originate from Upset’s upset of Man o’ War was discovered by researcher George Thompson. He found the following citation in a July 1877 edition of the New York Times referring to the horse racing that day:

The programme for to-day at Monmouth Park indicates a victory for the favorite in each of the four events, but racing is so uncertain that there may be a startling upset.

There, plainly stated, is the modern sports-related usage of the word “upset,” and it is is a newspaper a full forty years before Upset defeated Man o’ War.

Now, this does not mean that Upset’s defeat of Man o’ War did not popularize the term, but despite it being such a great story that you almost want to follow the advice of the newspaperman at the end of The Man Who Shot Liberty Valance (“when the legend becomes fact, print the legend”), it is not true.

Man o’ War and Upset raced again, by the way, and Man o’ War avenged his loss. Again, it was the only loss of his career.

Thanks to for the quote, thanks to Fred Van Ness and the New York Times for the story of the 1919 race and thanks to George Thompson and the New York Times for the evidence of the term’s 19th Century usage.

HORSE RACING URBAN LEGEND: A side bet inadvertently led to the first American Triple Crown winner in horse racing history.


Due to his being a character on the popular HBO program, Boardwalk Empire, early 20th Century mobster Arnold Rothstein has become a well-known name again (not that he ever was obscure, of course). However known or unknown he was by the general public, though, he has always been a bit of a legend in the world of sports gambling. For decades (nearly a century now!) people have debated over exactly what role he played in the infamous 1919 Black Sox scandal. At the very least, he knew that a group of Chicago White Sox players had been paid to throw the 1919 World Series against the Cincinnati Reds and he profited greatly from that information. At most, he financed the entire operation. I tend to believe that the latter assertion is closer to the truth of the matter. In any event, while his involvement in baseball gambling will likely be his sports gambling legacy, Rothstein was actually far more interested in horse racing.

Not just gambling on horse racing, though (which he did plenty of) or fixing horse races (which he also did plenty of), but Rothstein just plain ol’ enjoyed horse racing period. He would often attend races with his wife, Carolyn, especially at Belmont Park (as Rothstein “worked” in New YorK). While he would bet remotely if he couldn’t be at the track, he preferred being there for the live events. Over time, he began to fancy himself a bit of an expert on horses. And what better way to express this expertise than by gambling? This led an amazing bet between Rothstein and a horse owner, John Kenneth Leveson (JKL) Ross, which inadvertently set the stage for the first horse to win the American Triple Crown.

JKL Ross was born to one of the co-founders of the Canadian Pacific Railway, so when Ross’ father passed away in 1913, Ross inherited sixteen million dollars! Two years later, Ross entered the world of Thoroughbred ownership and breeding. He hired jockeys Earl Sande, Carroll Shilling and John Loftus as well as trainer H. Guy Bedwell. All four of those men are currently enshrined in the United States Racing Hall of Fame, so Ross definitely knew how to pick his employees. He also seemed to know how to pick horses, as one of the first horses he ever bought, Damrosch, won the 1916 Preakness Stakes!

Thus we come to early 1919 and the months leading up to the forty-fifth running of the Kentucky Derby in May of that year. Ross was eating dinner in a Manhattan restaurant one day when he was approached by another gentleman. He wanted to make a bet with Ross on the upcoming Derby. Ross later recalled that he expected the bet to be for $100 or something like that. Instead, the bet was for $50,000 (I’ve seen the story told differently – some say $20,000 and some say $50,000 – the $50,000 version appears to be more common – it’s hard to say which one is more accurate). It was right around this point that Ross realized that he was dealing with Arnold Rothstein.

The bet was this – Rothstein would bet that Eternal, a horse owned by James W. McClelland, would finish higher than Ross’ horse, Billy Kelly. The catch was that the winning horse would have to place in the race (finish first, second or third). So, entering the race, Ross had a clear strategy. He had two horses running in the race. Jockey Earl Sande was given the choice of which one to ride. He chose Billy Kelly, leaving the other horse, Sir Barton, for fellow Ross jockey Johnny Loftus. The strategy was that Sir Barton would be the “rabbit” – he would run strong early to dictate a fast pace, wearing out the other horses and then fall back at the end to allow his fellow horse, Billy Kelly, to win the race.

However, all Ross really needed was for Billy Kelly to finish ahead of Eternal and to place. Eternal had a tough go at it that day (some folks believe that the wet track was his undoing) so he was quickly out of it. So it soon became apparent that it was going to be either Sir Barton or Billy Kelly. Interestingly, Sir Barton’s trainer, the aforementioned Bedwell, had bet on Sir Barton to win. Whether that was just an informed guess or whether he knew what was about to happen, Bedwell’s bet proved prescient, as Sir Barton did not slow down as originally planned. Loftus would later recall, “I stood up in the stirrups and looked around to see where Sande and Billy Kelly were” and that “[s]seeing nothing of Billy Kelly, I gave Sir Barton a cut of the whip and he jumped off as if it were the start. Then I rode him the rest of the way, figuring to hell with Bedwell, Sande and Billy Kelly.” Since Billy Kelly was close behind Sir Barton most of the way, Loftus’ story seems a bit suspicious, as it seems he more likely just decided “to hell with them” and went to win it. Of course, little did he know that Bedwell had bet on his horse to win (maybe Bedwell knew Loftus’ personality that well?).

In any event, Billy Kelly placed second (the first time the same stable had the top two finishing horses) and Ross collected $20,825 for Sir Barton winning the race, $2,500 for Billy Kelly finishing second and $50,000 for Billy Kelly defeating Eternal.

This story is, in and of itself, pretty cool, but what makes it even cooler is that Sir Barton then went on to win the Preakness Stakes, the Withers Stakes and, to complete the first American Triple Crown (before the term even existed), the Belmont Stakes. Had he not served as a rabbit in the Kentucky Derby, there is a very good chance that the horse would not have won the Derby and thus, would not have won the Triple Crown. So his success really did appear to be owed to, of all things, a side bet between his owner and a mobster.

Thanks to Jim Bolus’ Remembering the Derby and Kentucky Derby Stories, Dorothy Oars’ Man o’ War: A Legend Like Lightning and David Pietrusza’s Rothstein: The Life, Times, and Murder of the Criminal Genius Who Fixed the 1919 World Series for the information on this story! Thanks to reader Terry Crow for suggesting that I feature this legend!

HORSE RACING URBAN LEGEND: Christopher Chenery ended up acquiring Secretariat by LOSING a coin toss!

STATUS: True (with a sizble cavaet)

One of the key ways that a famous male horse racing champion horse can create revenue for its owner is by selling the right for other owners to have their female horses (mares) mate with the famous horse, with the intention of giving birth to a horse that could be a legitimate horse racing champion in the future itself. Such “stud fees” nowadays can get into six figures for particularly impressive horses.

That was the situation that Ogden Phipps had with his famous stallion, Bold Ruler, who had finished fourth in the 1957 Kentucky Derby. A strong and durable racehorse, Bold Ruler was a much-desired stallion for breeding purposes. A problem, of sorts, for Phipps and “Bull” Hancock (owner of Claiborne Farms, where Bold Ruler had retired to – so Hancock had an interest in the horse, even though the Phipps family still controlled him) was that they did not have access to the best mares to mate with Bold Ruler for their own breeding purposes. They certainly could sell the right for other horse owners to have their mares breed with Bold Ruler, but the progeny would be owned by the other horse owners.

Thus, Phipps and Hancock came upon an idea – they would offer a proposition to the owners of the great mares out there. They would waive the stud fee and in return, they would get half of the horses that were born as a result of the studding. This is similar to arrangements that go on today, except they had a twist back then – a coin toss would determine who would get first pick among the horses born.

Here is where it gets a bit tricky. Christopher Chenery, a horse owner who had a nice variety of prize mares, agreed to the deal. He brought two of his finest mares to breed with Bold Ruler – Hasty Matilda and Somethingroyal. They each were impregnanted by Bold Ruler in 1968. The following year, Hasty Matilda was replaced by another mare named Cicada. In 1969. Somethingroyal got pregnant again, but Cicada proved to be barren. That’s the tricky part – the terms of the coin toss were that the winner of the toss got first pick of the horses born in the first year and then second pick in the second year. Well, obviously, there WAS no second horse the second year. So whoever “won” the coin toss would get one horse while the “loser” would get two. However, the winner would still get to determine which horse they would get, and since Phipps and Hancock were specifically looking for mares, when they won, they gladly took the filly (the term for female horses under the age of three) born of Somethingroyal, leaving the young colt (male horse under age three) from Hasty Matilda to Chenery and whatever Somethingroyal gave birth to (Somethingroyal was due in early 1970 – the agreement involved the assumption that Somethingroyal WOULD give birth – if something went wrong, she likely would have been bred a second time with Bold Ruler at no extra cost).

Naturally enough, that unborn horse turned out to be Secretariat, one of the most famous race horses of all time.

The other colt turned out to be pretty much unsound and was eventually sold for $50,000 just because of its lineage. The filly was named The Bride and while she turned out to be quite slow (which was funny, considering she was the sister of Secretariat, for crying out loud!), she turned out to be a valuable breeding horse, giving birth to two notable race horses herself (genetics are quite important in horse breeding!).

So while it is not simply a case of, “Oh man, we lost – oops, we won!,” it is still a very interesting case of a bet going into interesting directions (Phipps never did the beet system again – even before Secretariat was born he decided he did not like the idea).

Okay, that’s it for this week!

Feel free (heck, I implore you!) to write in with your suggestions for future installments! My e-mail address is

-Brian Cronin

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