Harry Kakavas may not be the biggest loser, but he has made a point of being a repetitive loser. He could be sentenced to 28 years in prison if he fails to pay up. Today, Watanabe has covered almost his entire debt except for $15 million for which he faced four felony charges back in 2009 and again in 2020.
He tried suing the casinos, but ultimately lost and was ordered to pay off his debt. So far as famous gamblers who lost it all go, Watanabe’s losing streak is believed to be the biggest Las Vegas has ever seen. Whether he was bored or wanted to try something new, Watanabe’s gambling habits pushed him into more extreme scenarios year after year and in 2007 he incurred $127 million in losses at Caesar’s Palace and The Rio after gambling over $825 million. Watanabe inherited Oriental Trading Company in 1977 which he later sold in 2000. But if anything, Terrance Watanabe is truly one of the gamblers who lost it all, or at least a very substantial part of what he owned.
As it turns out, a lot of people who came into money, or made a fortune one way or another, have felt inclined to gamble rather foolhardily at one time or another. When we discuss the biggest gambling losers in history there is always a bit of a rivalry.
