1. Archie Karas – 1992 – After losing around $2 million during high stakes poker games in Los Angeles, Archie did what few people would do with their last $50… He went to Las Vegas. At Binion’s Horseshoe Casino, he stumbled into a close friend who lent Archie $10,000 to play some high stakes poker games. In a game called Razz, where the lowest accumulative hand wins, he quickly returned the $10,000 he was leant with 50% interest, and was still on a roll. This wasn’t just a one hit wonder of a night, Archie’s streak was just getting started.

He simply did not lose for about three years, and was continually building his wealth. In total, Archie won around $40 million in three years. However, like so many gamblers, he eventually blew it. He lost around $11 million by playing craps over a three week span. He then tried to reverse his luck with baccarat, but he ended up losing $17 million more. And then managed to gamble away the rest of his lucky fortune. He is known as one of the streakiest gamblers of all time. His real name is Anargyros Karabourniotis.

2. Sean Connery – 1963 – Sean Connery was known to be no stranger to gambling, as his father was an avid gambler. Connery followed in his footsteps and was known to occasionally enjoy a stop at the casino. On one particular trip in 1963 to an Italian casino located in the Alps, Connery went on a magical run in the game of roulette. After a few losing rolls with his money on 17, he then won, and then won again, and once again. At odds of 50,000 to 1, Connery won over 17 million lire. Till this day, many roulette croupiers say the the commonly played number is “17.”

3. MIT Students – 1992 – A devoted team of MIT students employed the tactic of card counting to swindle millions from unsuspecting casinos across the globe. Mainly in the United States, these MIT students were often treated like royalty at these casinos that they had established themselves as high rollers at. They were often given executive suites and VIP treatment throughout their successful run. As the team grew, some members got into trouble. For example two team members which were a married couple, both were caught counting cards in the Bahamas and thrown in jail while their money was confiscated. They never played for the team of players again. Over 20 years later, a movie was produced roughly based on their achievement of the greatest card counting scam in history. This movie was called “21” and featured Kevin Spacey.

4. Don Johnson – 2011 – An avid gambler, Don Johnson made history as he won a total of $15 million spread out from three different casinos in only six months. He did this, in part, by seeking out the casinos with the most player-friendly rules, and played at particular tables where they were using an optimal number of card decks. This along with some other strict criteria for the style of dealer at the table enabled Don to really put the odds in his favor. Another huge piece was that he personally negotiated a 20% payback, where as some casinos offered a standard 10% payback, if any at all, for the purpose of luring in new customers. Through this tactic, Don ended up accumulating his $15 million fortune without counting cards or any cheating.

5. Charles Deville Wells – 1891 – “Bankrupting the Bank” is the term used when a player in a poker game wins ever chip at the table, and it’s considered an extremely impressive task. Charles Deville Wells did just that in 1891 at the Monte Carlo casino as he won around one million francs. Wells was commonly known to be a cheater and a scam-artist, but managed to pull off such a great feat in a game of luck over an 11 hour period. It helped gain him worldwide fame from his accomplishment, even though like so many gambling stories, he eventually lost it all back at Monte Carlo a little while after.

6. Fred Smith – This is the Fed-ex Blackjack story that is the sole reason for federal expresses existence to this day. Fred Smith the Yale graduate who came up with the idea for premium delivery services was down to his last $5,000 and had a $24.000 fuel bill due for Fedex in the early days. So Fred went to Las Vegas, Nevada and bet it all on Blackjack as recounted below:

““I asked Fred where the funds had come from, and he responded, ‘The meeting with the General Dynamics board was a bust and I knew we needed money for Monday, so I took a plane to Las Vegas and won $27,000.’ I said, ‘You mean you took our last $5,000– how could you do that?’ He shrugged his shoulders and said, ‘What difference does it make? Without the funds for the fuel companies, we couldn’t have flown anyway.’ Fred’s luck held again. It was not much, but it came at a critical time and kept us in business for another week.”

The result of that lucky Vegas trip is a Memphis, Tennessee company that today is valued at 46.33 Billion dollars and Smiths net worth hovers around $3 billion himself.

7. Jon Price Sports Information Traders – There are touts that you see on CNBC shows like Steve Stevens and then there are legends that fly under the radar while making millions of dollars betting on sports. With a knack for analytical research and numbers Price is known for running his sports advisory operation at Sports Information Traders like a hedge fund while cashing in for millions of dollars consistently year over year. Recently he made headlines for making over a million dollars wagering on Floyd Mayweather over Manny Pacqauio despite the public betting heavily on Pac-Man. In the hall of fame of sports betting Jon Price certainly ranks at the top.