Investors have sometimes been compared to gamblers, with both risking money on an expected outcome in hopes of increasing their wealth. Now a losing gambler is taking a page from investors whose nest eggs have vanished: He's suing to recoup hundreds of millions in losses.

Syrian billionaire Fouad al-Zayat lost $350 million gambling over the last 15 years and has sued six major British casinos to get a large chunk of that back.

Al-Zayat is no stranger to trouble, or getting out of it. Earlier this month a judge cleared the businessman, who made his fortune in aviation, construction, investment, and oil, of having to pay an eight-year-old $4 million gambling debt to Aspinalls of Mayfair, a London casino.

England's High Court ruled that Aspinall's broke the 1968 Gaming Act by agreeing not to cash al-Zayat's check for 12 months -- as he asked them to -- while he continued gambling.

The judge equated this with issuing credit; British law forbids casinos to do extend credit, to prevent them from encouraging people to gamble with money they don't have.

But how else does a proprietor reward such a good customer?

According to case documents, al-Zayat visited Aspinall's 600 times in 12 years, betting $161 million and losing $40 million. Al-Zayat is a fixture on London's exclusive gambling tables, having played next to Tom Cruise, members of the Saudi and British royal families, the Sultan of Brunei, and the arms dealer Adnan Khashoggi.

He earned the nickname "Fat Man" from casino staff for his girth, which matched his generosity -- he often tipped thousands of dollars a pop.

Now he claims the casinos owe him money -- around $118 million, the same amount he claims he was given in illegal credit from 1989 to 2003.

"The casinos woo you, they make it their business to become your friends," he told the Guardian. "I have been called by them on birthdays, and relatives' birthdays; they try to become part of your life. When you go to them, you are offered the best hotel rooms and anything you may want, in order to get you to continue gambling. If that means giving you credit, and breaking the law, they will do it."

Al-Zayat knows about how to make important friends. U.S. court documents cite him as having given disgraced Congressman Robert Ney tens of thousands of dollars in gambling chips. Ney, Republican of Ohio, was sentenced to 30 months in jail in 2006 on conspiracy and perjury charges in relation to the Jack Abramoff scandal.

Fresh off his victory of winning an appeal over Aspinall's, al-Zayat may be able to, again, beat the house.

by Andrea Chalupa