1. Terry Watanabe: This high roller reportedly lost around $204 million playing various casino games in 2007.
2. Harry Kakavas: He lost an estimated $164 million in a little over a year at the Crown Casino in Melbourne, Australia.
3. Akio Kashiwagi: A Japanese businessman known for his large bets, he lost around $10 million in a single baccarat game in 1992, and his total losses have been estimated to exceed $100 million.
4. Charles Barkley: The former NBA player has admitted to losing over $10 million through gambling over the years.
5. Archie Karas: Although initially famous for turning $50 into over $40 million, he later went on a losing streak and eventually lost it all.
6. Robert Maxwell: The British media tycoon lost an estimated £1.5 billion ($2.3 billion) at the casinos in a short timespan before his mysterious death in 1991.
7. Kerry Packer: The Australian billionaire lost around $20 million in a single session playing baccarat in 1999.
8. Zhenil Ye Gon: A Mexican businessman who lost an estimated $127 million playing baccarat in a Las Vegas casino.
9. Maureen O’Connor: The former mayor of San Diego lost over $1 billion through gambling over a nine-year period.
10. Frank Sarakakis: A Greek businessman who reportedly lost around €20 million ($23 million) in a casino in London.
Please note that the specific amounts and details may vary, as some losses are based on reported estimates, and in some cases, individuals may have lost amounts higher than those mentioned.