There have been many notorious casino high rollers and many are characters, some are even infamous for not meeting their casino bills; amongst these casino shirkers, amongst these we find Syrian businessman Fouad al-Zayat. Due to unpaid casino bills in London where he lost $46 million and wrote a bad cheque for $4 million; he also lost all of his assets including a Boeing 747.

Perhaps not a shirker, but Allan Iverson gambled his way through most of the $200 million he made during his NBA career, he still plays as a pro ball play, however he has been tainted by the gamblers tar brush, particularly in light of the fact that he was banned from many Las Vegas and Atlantic City casinos.

The late Stu Unger; Gin Rummy and poker player extraordinaire – said to have more natural talent in Texas Hold 'em than any other player ever, living or dead! Gambled and lost his way through more than one fortune, he died with no assets to his name, spent his way through $30 ,million and poker playing friends raised a collection to pay for his funeral services. He was continually running from gambling debt, even at the young age of 18.

One of the most well known high rollers of all time was the richest man in Australia – the late Kerry Packer and none of the aforementioned gamblers were in his league. Mr. Packer did not however leave his casino bills unpaid; he had the money to more than indulge his vice for gambling and sports, and according to Forbes had amassed a fortune of AU$4.2 billion in the year before he passed away, which has left his family quite comfortably off.

Kerry Packer always did things in a larger than life way; his gambling was the same. It is reputed that during one 1999 losing streak in London, he lost almost $28 million. This took him only three weeks and in total it is said he lost $40 million during a 10 month stint with bad luck, but this hardly made a dent in his resources.

There is one instance in which a Texas oilman bragged to Terry Packer that he was worth $100 (the amount varies) he pretended to be suitably impressed and said "Really..$100million?", "yes I am, sir" said the oilman, never one to shirk confrontation, Packer replied, "I'll Toss You for It!" The Texas oilman went away; Terry Packer became world renowned for this quip and "I'll Toss You for It!" became the title of one of his motivational books. His Vegas antics, drool with drama like this and in one winning streak at Caesars Palace he won $9 million. This represented half of that quarters' profits, they reported a very poor quarter indeed.

All gamblers are keen on proposition bets and there have been some real doozies made over the years, perhaps the best, or should we say worst of them was when Brian Zembic was wagered he would not get a boob job, and wear these for a year. He did it and won $100000!