The Biggest Gambling Scandals in History: Tales of Cheats and Con Artists

Many of the best movies on gambling scandals are about people who are, if not outright cheating, at least exploring gambling strategies that go against the house’s wishes. Some of these strategies fall into a category that prosecutors like to call “illegal.” Others will just result in a blanket blacklist from casinos all over the country.

Either way, it makes for good reading. In this article, we take a look at some famous tales of cheats and con artists.

The Black Sox Scandal

Most professional sports prohibit players from participating in betting. There are many practical reasons for this, such as players having too much insider information. Wagers could give them conflicting motives out on the field. It could even encourage them to cheat.

Such was the case with the “Black Sox” scandal of 1919, in which 8 White Sox players were accused of deliberately losing the World Series to rake in gambling money. Their alleged co-conspirator was an infamous gangster by the name of Arnold Rothstein.

The players were prosecuted and acquitted but forever banned from major league baseball.

The MIT Blackjack Team

The MIT Blackjack Team has been much discussed in popular culture thanks to a book called “Bringing Down the House,” by Ben Mezrich—a book which loosely translates actual events into a fictional narrative, and the film, “21,” which reinterprets the book. On the flip side, we have an interesting tale of 6 college students (more eventually joined) who went to Atlantic City to test their math skills at counting cards at blackjack.

Note that while casinos are not very fond of card counters, there is nothing illegal about the practice at all (though the aforementioned film suggests it’s a strategy that might result in a parking garage beat down).

Card counting helps players decide when to fold, when to do a blackjack double down, when to raise and so on.

The Roselli Brothers

The “Roselli brothers,” as they called themselves were scammers from the early 2000s, who stole people’s identities and used them to open up lines of credit at major casinos in Las Vegas, Atlantic City, and several other locations.

Once they got the money, they’d keep it for themselves and move on to the next con. This went on for years, during which time they stole an estimated $10 million.

Authorities later found out that the name “Roselli Brothers,” was actually a pseudonym. To this day, nothing is known about the perpetrators of this successful campaign of casino cheating.

Phil Ivey's Edge Sorting

Phil Ivey along with a partner took home more than $10 million at the card tables over the course of just a few visits. Even by [professional gambler] standards, that’s an overwhelmingly good haul.

He managed it by using a strategy known as “edge sorting.” The player scans the backs of cards looking for design imperfections that betray what the card being dealt is. It’s an imperfect art form that hinges on the idea that cards are printed with very minor flaws on the back checkered patterns that give something of their contents away.

Reading the back of cards is not illegal, though the technique necessary to do it is often considered questionable. The imperfections are usually only apparent when the card has been turned at a 180-degree angle. Players must ask the dealer at a live casino to reposition cards on the table, usually under the pretext that it will bring them good luck.

Of course, shuffling the cards will disrupt the orientation. Therefore, the player must also ask the dealer to use an automatic shuffler to keep the cards in the desired position. The longer the game is played, the more information the edge sorter is given.

Phil Ivey was eventually required to pay back a significant portion of his earnings—not because his strategy was illegal but because he kept coming back to casinos even after being asked not to return.

The Tran Organization The Tran Organization was a notorious card cheat gang of the early 2000s. Most participants of said gang belonged to a single family—the Trans—a husband and wife who used extended relatives and other connections to cheat casinos out of millions.

Unlike many of the scammers on our list, the Tran family didn’t worry about finding loopholes. They cheated brazenly. Microphones. Bribed dealers. Illegal software. Tables crammed with planted players. However, they didn’t target slot machines.

Their scams involved around 40 people in total, most of whom have since been prosecuted for their involvement.