Famous Chicago Gamblers

September 16th, 2011 | by Frank | No Comments »

Famous Chicago Gamblers

With the potential onslaught of casino action to come in Illinois, the land of Lincoln may eventually become known as the land of the slot machine. Rivers Casino is the next in what is an increasingly long line of new gambling options in Illinois.

Chicago already has a long, celebrated history of gambling. Who are some of the most famous—and infamous gamblers in Chicago history?


The Chicago Black Sox in 1919 are part of one of the most notorious chapters in Chicago gambling history.

Eight members of the Chicago White Sox were banned for life from baseball for intentionally losing to the Cinncinati Reds in the World Series. For Cub fans, not getting to the World Series might be seen as a badge of honor in light of such a disgraceful act.

One of the instigators of the 1919 scandal was White Sox first baseman Arnold “Chick” Gandil. Gandil was in cohorts with Joseph “Sport” Sullivan, a professional gambler. Together they put in the fix that would forever change Chicago baseball.

Charles Comiskey, who many of the players hated for his misery and spiteful ways, was a prime motivator for the fix. Some members of the team felt Comisky had deliberately shorted them on performance bonuses on their contracts.

Starting pitchers Eddie Cicotte and Claude “Lefty” Williams, outfielder Oscar “Happy” Felsch, and shortstop Charles “Swede” Risberg were all in on the fix.

Third baseman Buck Weaver was asked to participate, but did not. Nevertheless, Weaver was later banned with the others for knowing of the fix but not reporting it. Although he hardly played in the series, utility infielder Fred McMullin got word of the fix and threatened to report the others unless he was in on the payoff.

With dishonor of that order, this team was truly in a class by itself.

Star outfielder “Shoeless” Joe Jackson was also mentioned as a participant, though his involvement is disputed.

In Jackson’s own words, he was innocent: “When I walked out of Judge Dever’s courtroom in Chicago in 1921, I turned my back completely on the World Series of 1919, the Chicago White Sox, and the major leagues. I had been acquitted by a twelve-man jury in a civil court of all charges and I was an innocent man in the records. I have never made any request to be reinstated in baseball, and I have never made any campaign to have my name cleared in the baseball records….

If I had been the kind of fellow who brooded when things went wrong, I probably would have gone out of my mind when Judge Landis ruled me out of baseball. I would have lived in regret. I would have been bitter and resentful because I felt I had been wronged.

But I haven’t been resentful at all. I thought when my trial was over that Judge Landis might have restored me to good standing. But he never did. And until he died I had never gone before him, sent a representative before him, or placed before him any written matter pleading my case. I gave baseball my best and if the game didn’t care enough to see me get a square deal, then I wouldn’t go out of my way to get back in it.”


The percentage of pro athletes who gamble on sports is greater than the percentage of the general public that does. Pro athletes have high levels of energy, unreasonable expectation, very competitive personalities, distorted optimism, and high IQs, either street smart or book smart.”

Arnie Wexler

Perhaps the greatest competitor in Chicago sports history, Michael Jordan, is also one of our city’s most renowned gamblers. As Jordan has said, “I’ve gotten myself into [gambling] situations where I would not walk away and I’ve pushed the envelope.”

“It’s very embarrassing … one of the things you totally regret. So you look at yourself in the mirror and say, ‘I was stupid.’ ”

As a college player at North Carolina, Jordan bet teammates on how many free throws he could make, and on games of “Horse.” As a pro, Jordan enjoyed playing poker when the team travelled.

While facing the Knicks in the playoffs in 1993, the New York tabloids learned that Jordan had gone down to Atlantic City to play the tables the night before a game. Although athletes gamble in their off hours all the time, for some reason it was “news” that Jordan was off playing cards during the playoffs. Shades of Broadway Joe, I guess.

Gambling on golf is Jordan’s true passion. It is said that millions of dollars have changed hands between Jordan and fellow linksmen.

“I want people to understand, gambling is not a bad thing if you do it within the framework of what it’s meant to be, which is fun and entertaining,” Jordan has said.


James Butler Hickok was born on May 27, 1837 in Homer, Illinois. “Wild Bill,” was a lawman, gunslinger and a very good poker player.

Early on, Wild Bill was a stage coach driver who spent many a night after work in saloons drinking and watching his back, lest some poor loser try to take him out from behind for beating him at poker.

Wild Bill followed the herd of men seeking instant riches via the gold rush.

Hickok died in 1876, at the hands of a bitter gambler who pretended he wanted to look at the hand Wild Bill was playing. The coward shot him in the head. The hand that Wild Bill Hickok was holding at the time was two aces and two eights. Thereafter that hand became known as a “dead man’s hand.”


The house doesn’t beat the player. It just gives him the opportunity to beat himself. ~Nick Dandalos

Legendary gambler Nick “The Greek” Dandolos lived in Chicago, and also spent time in Montreal, Vegas and elsewhere. In 1949, Dandalos sat at a Vegas table with fellow card shark Johnny Moss. Dandolos played Poker for five months, stopping only for sleep. Although Dandalos won $500,000 in one hand, he ended up giving it back and then some, losing $2,000.000 by the time he the last hand was dealt. The game was set up by Benny Binion as a tourist attraction, and is the inspiration for the modern day World Series of Poker.

Dandolos was known throughout his life for winning and losing large sums of money. After winning over $500,000 on horse racing, he moved back to Chicago where he lost it all on card and dice games.

Nick the Greek gambled with many mob bosses, including Al Capone, Dutch Schultz and “Legs” Diamond.

One urban legend claims that Dandolos once had the opportunity to escort Albert Einstein around Las Vegas. Thinking that his gambling friends may not be familiar with him, Dandolos allegedly introduced Einstein as “Little Al from Princeton” and stated that he “controlled a lot of the numbers action around.”


One of the most legendary Chicago gamblers in the 1870s was Mike McDonald. McDonald was a political boss who helped build the infamous Chicago “Machine.”

During this period, police often looked the other way and allowed gambling on card games, checkers, backgammon, horse races, and prize fights. They played policy, a lottery-like game. By the 1850s rowdy crowds gathered and gambled at rat and cock fights.

Gambling became a major business. By 1850, entrepreneurs established hundreds of gambling houses, along with saloons, especially downtown. By 1866, “pool rooms” accommodated racing fans away from the track. Gambling payrolls, rents, and customers’ purchases in adjacent businesses were important to the city’s economy.

“King” Mike elected mayors, hung with presidents, and racked up serious winnings. He was integral to the start of organized crime in Chicago.

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