Pittsburg Phil: ‘A Big Loser,’ 1897

Jul 13th 2012 11:00 am |

Pittsburg Phil, 1903

Pittsburg Phil has been a frequent subject at Colin’s Ghost since we founded the site in 2008. While doing research into horse racing history in newspapers from the 1890s, I frequently come across the name of the great gambler. The vast majority of reports or mentions of Phil in contemporary sources support the mythical elements of his story. In Pittsburg Phil’s appearances in newspaper accounts, he is distant, held in reverence by writers of his day.

The Racing Maxims and Methods of Pittsburg Phil, published after his death in 1905, fully formed and essentially finalized the legend that news writers started during his life. The Pittsburg Phil legend is of a near perfect horseplayer with a mind as sharp as a fine blade and the discipline of a monk. While accounts of his losses were not uncommon, stories of his success far exceeded those of failures. So, imagine my surprise when I came across an article in the Philadelphia Inquirer with one of the most intimate profiles of the great gambler that makes the legendary figure appear, well, human.

In the article, an unnamed writer claims to have visited Phil in his hotel in New York during a string of bad luck. Not only does Pittsburg Phil come clean about his losses and his string of undisciplined play, but the article described the “greatest bettor of the American turf” in all the detritus of the horseplayer’s life. Here is how the┬áreporter described the scene in the summer of 1897:

Phil told me all about his winnings and losses this season and last season at the Imperial Hotel yesterday. I met him in the reading room, where he was straightening out his accounts for his betting on Tuesday’s races.

“The table at which he sat was littered with paper – papers of two distinct kinds. One sort, betting slips and memoranda, represented in cold, relentless figures the amount of his losses on Tuesday at Sheepshead Bay race course, and all debits, all to be entered on the wrong side of ‘Phil’s’ ledger – vouchers for the great plunger’s ‘Black Tuesday.’

“Not a single credit slip in the lot; nothing to subtract from the sum total of his losses. All the bookkeeping was confined to the first and simplest rule in arithmetic, the mere addition of what he and his commissioners had returned to the source from which it had originally came.

The “commissioners” referred to are men Pittsburg Phil hired to place his bets. Knowing that his wagers had the power to significantly drop the odds on any horse he bet, he instructed proxies to make bets for him with explicit instructions on required odds on his picks. More on that from the man himself later, but back to the description of Phil in his room at the Imperial in 1897:

Phil on the same table were copies of all the local dailies, with more or less detailed accounts of how and why he had lost his money. There never was a betting man yet who was as omnivorous a reader of everything bearing on his favorite sport.

“But for all the enormously expensive nature of the work he was doing at that table Mr. Smith was as clean shaven, as pale – but no paler – and as imperturbable as ever, just as impassive as he is when a driving race is finishing that may mean scores of thousands for or against him.

What did it amount to after all? The ring had simply won back some of their own money, and ‘Pittsburg Phil,’ good loser, as he is a quiet winner, was quite ready to talk calmly and impartially about the most disastrous day’s racing he had known in many a long season, he played five races and failed to win a bet. His losses on the day footed up $40,000.”

After describing the scene, the reporter then quoted Pittsburg Phil at length, in one of the few in-depth quotes from the man himself taken during his lifetime. Gone is the bravado found in Maxims when his words were channeled through journalist Edward Cole long after his death. His words offer insight into the pitfalls of high-stakes betting in the days of the bookmaker. More importantly, it is Phil the horseplayer, with all of the honest self-critique common in anyone who is good at their craft:

“‘Many persons seem to think,’ said Phil, ‘that every time I bet I win, but I am sorry to say that it is not so. Since the season opened I have battled with more or less success against the books…

“‘Tuesday was the first time in my life that I ever overbet myself, and the big prices laid against the horses I fancied, and the eagerness of the bookmakers to take all the money I gave them was responsible in a great measure for my losses…’

“‘For instance, in the race which Song and Dance won I told my commissioners to keep on backing Souffle as long as they could get 2 to 1 to win and 4 to 5 to place. After they had gone some time I realized that I had failed to limit my commission, and I went looking around the ring in the hope that I would be able to see some of them and tell them to stop playing the mare; but I couldn’t find them, and when I figured out the money I had bet on the receipt was over $16,000. That is only one of many instances in which I overplayed myself on Tuesday….’

“‘I was betting recklessly, and winning at the odds I was getting on my money would have made me a great winner. Betting big money on a races is frightful strain on a man’s system. I have frequently gone to the race track with the determination not to bet more than $500 on a race, but I tell you, I find out when I get in the betting ring that resolutions are all well enough in their way, but the temptation to bet is too strong, and I soon find myself playing as high as and sometimes higher, than I ever played before in my life.’

“‘The habit seems to grow on a man, and he can’t stop. I would give a lot of money to be able to go to the race track and only bet $500 on a race.”

I have bought into a long-standing myth about the ability to beat the races in the era before the widespread dissemination of past performance data. As this account proves, even a gambling legend could get burned by the same mistakes that horseplayers make today.

Pittsburg Phil will forever be remembered as the founding father of the modern horseplayer but it’s important to remember that even his life, where he fully dedicated himself to beating the game, ultimately ended in failure. Less than eight years after this account, he was dead at the young age of 42. Those who knew him said, in the end “his nervous system [had] been shattered because of the intense strain and worry caused by his extensive operations on the turf.”


“A Big Loser Talks Calmly on Betting,” Philadelphia Inquirer, 29 August 1897

Read all posts about Pittsburg Phil from Colin’s Ghost

Sorry to say i’m going to be out of town for this year’s Delaware Oaks and Delaware Handicap…

Thanks for reading and good luck!

Filed in thoroughbred racing history

2 Responses to “Pittsburg Phil: ‘A Big Loser,’ 1897”

  1. Owen says:

    As I work on finishing “Three For the Money, A Brief History of Thoroughbred Racing in Windsor (ON,)” articles such as this help me explain the colourful past of the Windsor Jockey club at the turn of the 19/20 C. Thanks.

  2. Tim Peterson says:

    Very nice tribute to Pittsburg Phil on day of the 150th anniversary of his birth! He led an extraordinary life rising from working in a cork factory in Pittsburgh to competing with the titans of the day on the turf in New York. If horse racing ever gets around to starting a Horseplayers Hall of Fame, Pittsburg Phil would be an automatic inaugural class inductee.