Known only as a 25-year-old from Los Angeles, this man’s lucky dollar netted him a win of $38.7 million. In 2003, an anonymous software engineer decided to try his luck at the Excalibur hotel’s casino by popping one dollar into a Megabucks Jackpot machine. 3 Know your limits The Winners Archie Karasīetween 19, Greek American, Archie Karas, became a legend on the Las Vegas strip after a winning streak left him in profit to the tune of a whopping $40 million – not bad for somebody who started with an initial bet of just $50.