If you have a few minutes its well worth the time to read the in depth article on George E. Smith, better known as “Pittsburg Phil”. [Link below] While he died young in 1905, he was one of the pioneer handicappers in the sport. He amassed an amazing fortune in race wagering in an era well before the parimutual system became the standard in 1940 with US racing.
His earnings didn’t come from a scam or con and shouldn’t confused with such stings as Gay Future then 1970’s runner using a switch. Rather he simply employed observation skills like none other.
Per the article his fortune (almost all from race wagers) upon his death at 43 was nearly $2M USD which in 2010 dollars is around $46,500,000 per that inflation calculator. This from a guy who rose from utterly nothing. He had been a cutter in a Pittsburgh cork factory since he was 12, began betting on his own game chickens at 14, and at 16 entered a poolroom where serious gambling was done.
Phil was alone among the spectacular bettors of his time – a headline-grabbing era of high-rollers, sporting owners, and larger-than-life match races – in that he never went broke or lost his nerve betting ungodly sums of money. His scores put a dozen or more bookmakers out of business.
The story link from The Daily Racing Form (June 24, 2011)
Smith listened and thought about the races for a year before he made his first bet, in the fall of 1879 – a winning one on a horse named Gabriel at the Brighton Beach course. He quit his job, ran his bankroll from $500 to $5,000 in two years, then destroyed the Pittsburgh poolrooms for $100,000 before he ever walked into a racetrack. That introduction came at the 1885 Kentucky Derby, an experience that encouraged him to move his tack to Chicago, where he was unknown. At Silver Bill Riley’s poolroom he gained his nickname – there were too many Smiths in the room, so when Smith told Riley where he was from, Riley, thinking of Pittsburgh and Philadelphia in the same note, christened him Pittsburg Phil.
Phil also took in the races at Washington Park and the West Side Driving Park, and using his binoculars he could now compile more accurate charts. His gift for observation was forged here. He’d watch all of the horses, and not just the one carrying his money, their trips, how their jockeys rode them, how they pulled up after the race, if they were in distress or barely fatigued. He’d hurry to the finish line after the race to watch the condition of the horses as they were unsaddled. These were curious methods then.
He owned horses, placed wagers via straw men to throw off the bookies, and he did lose huge sums of money along the way too - but that often was just a way to gear up for a big score. Example:
By the fall of 1891, Phil was knee-deep in one of his few bad seasons. Yet he knew the time was right for one colossal bet. King Cadmus had been training well, and Phil believed his speed and class were underestimated against other juveniles he felt he had accurately gauged. He ran King Cadmus three times, twice against better horses, including in the celebrated Futurity Stakes, as a way to get him in shape and hide his ability. The next week, Phil entered King Cadmus in the Sapphire Stakes and planned to bet more than he ever had before.
Phil’s trustworthy friends were called upon as betting commissioners and orders sent out to poolrooms all over the country. As McGill remembered, “Phil read one line in a New York morning paper with a smile: 'The recent bad luck of the young Smoky City plunger, ‘Pittsburg Phil,’ persists. He hasn’t won a good bet in several weeks, and the bookmakers now take his money as readily as that of the veriest tyro.” King Cadmus would be a price.
King Cadmus won the race and with it a true fortune for Phil:
[His crew] counted their winnings as slightly more than $143,000. It was the biggest score the turf had seen.
Soon after, Phil took the bookmakers again at Sheepshead Bay – for almost $75,000 – on a mud-loving filly named Reckon at 12-1. His two-race gain of more than $200,000 would have been $2 million in the Roaring Twenties, McGill said, which means, adjusted for inflation, Phil’s score equates to more than $22 million today.
Amazing stuff of course near the very end the sport was changing, publications like the DRF gave the bettors much of the info Phil culled himself and the bookies became far more wise as dozens were put out of business by Phil. However during those glory years it was one heck of a ride!
This link has some some sampled headlines from back in the day with Phil in the media:
The website Colins Ghost has covered ‘Phil’ before too with great nuggets as well:
http://colinsghost.org/2008/05/obituary-of-pittsburg-phil-1905.html
http://colinsghost.org/2009/01/what-killed-pittsburg-phil-1905.html