Six of The Most Notable Wins in Gambling History – MoneyMade

Despite the difficulty of winning big, some gamblers are popular for beating incredible odds for substantial earnings. In no particular order, the following are some of the biggest gambling wins in history.
 

• Kerry Packer – The Billionaire Gambler ($40 Million): Considered one of the world’s greatest gamblers, Kerry Packer was an Australian media mogul and billionaire popular for high-stakes gambling. He was well known as a big spender, with several stories of Packer tipping casino staff hundreds of thousands of dollars after securing big wins. According to reports, casino workers in top establishments never called in sick or skipped work whenever the billionaire mogul was in town. Packer was known for his willingness to bet millions on the average game of Baccarat or Blackjack.

Packer also lost big a few times. Some stories have it that Packer once lost £19 million in one night. However, he returned and recovered all of it, plus an extra £7 million. One of his largest wins was in the early 1990s, when he gambled at the MGM Grand in Las Vegas and won up to $40 million in one night.
 

• Archie Karas – The Run ($40 Million): In less than three years, Anargyros Karabourniotis, aka Archie Karas, successfully earned $40 million, leading to “The Run,” a colloquial name given to his gambling streak. Karas moved to Las Vegas with only $50 in 1992 and later borrowed $10,000 to play high-stakes poker. At the end of the night, Karas had doubled the money. 

Interestingly, Karas consistently won several games, which allowed him to accumulate funds. Unfortunately, he ended up losing all of the money he made. The skilled gambler was arrested at least five times in Nevada and California and also ended up in jail for over 2 months. He was eventually banned from Vegas casinos for several alleged gambling scandals and currently remains on the gambling blacklist maintained by the Nevada Gaming Commission and the Nevada Gaming Control Board. 
 

• Elmer Sherwin – Megabucks Jackpots ($25 Million): Sherwin’s story highlights the possibility of exceptional luck contributing to a gambler’s likelihood of winning. Erwin Sherwin had tried his hands on Megabucks for several weeks, spending $100 on each try. One day, he tried again and lost, but took $20 from his wife instead of quitting, which changed his luck. Sherwin’s first win was a $4.6 million jackpot in 1989 at The Mirage in Las Vegas, when he was 76. Interestingly, Sherwin hit another Megabucks jackpot 16 years later at 92, winning $21.1 million at the Cannery Casino & Hotel in Vegas. Unlike many other big winners, Sherwin donated largely, spending extensive amounts on charity, as well as efforts towards Hurricane Katrina relief. Reportedly, Sherwin continued to live a modest life, even opting for periodic payments instead of accepting the lump sum. 
   
• Anonymous Las Vegas Engineer ($39.7 Million): A software engineer from Los Angeles visited Las Vegas in 2003. The 25-year-old engineer heard from his uncle about the IGT Megabucks machine at the Excalibur Hotel-Casino on the Las Vegas Strip and visited the hotel on March 31, betting $100 on the machine.

According to the engineer, he only looked away for a second after wagering the money, and saw the winning symbols all lined up when he looked back. He won $39,713,982.25, and set the record for the largest Megabucks win in Slot history. 
 

• Gloria MacKenzie – The Powerball Jackpot ($590.5 Million): Gloria MacKenzie was 84 years old in May 2013 when she won what was once the largest single-ticket lottery jackpot in US history. At the time, she won the $590.5 Million Powerball prize and decided to take a lump-sum payment of $370.9 million. 

The Florida resident entrusted most of the money to her son, Scott MacKenzie, who was allegedly misspending the money. Years later, she sued Scott, stating that her son and his investment manager poorly invested the funds and lived lavishly instead. The 40-page lawsuit accused her son of negligence, breach of fiduciary duty, and conspiracy to misrepresent, claiming she suffered damages worth more than $10 million. Unfortunately, Gloria died in February 2021 before the case could be finalized. She was 92 years old at the time of her death.
 

• Cynthia Jay-Brennan ($34.9 Million): Cynthia’s win is interesting because she was simply trying her luck at the former Desert Inn Hotel and Casino. While out with her boyfriend Terry Brennan, she decided to spend $100 on the Megabucks slot machine at the casino. Her final spin ended with the Megabucks symbols lined up on the screen, earning her $34.9 million.

Following her win, the cocktail waitress submitted a two-week notice and married Brennan. After a few weeks, she realized her life had changed significantly, and she could no longer be out in public without being approached. Unfortunately, an alleged drunk driver slammed into Cynthia’s car in March 2000, instantly killing her sister, Lela Jay, and paralyzing Cynthia.