We’ve been profiling famous people who have lost all their money for a while now. For this installment, we wanted to look at a celebrity who didn’t necessarily spend unwisely or lose all his money at once.

He’s known as “Mr. Las Vegas”. Wayne Newton practically invented the Las Vegas Review show that sparked the golden era of entertainment in “Sin City”. He got his start singing for other acts in Vegas; Lucille Ball, Bobby Darin, George Burns, etc. But in those days, a show in Vegas was a weekend affair, with the headliners usually driving up from Los Angeles and back home on Monday.

When Newton got his first chance at a headline act at the Flamingo Hotel, but instead of a weekend show every few months, he was a nightly fixture at the classic Vegas property. Critics practically laughed at him, saying he’d be playing to half-empty showrooms during the middle of the week. Turned out the opposite was actually the truth. Though he took Mondays off, Tuesdays through Thursdays, Newton played to packed houses of retirees and folks on vacation. He was a runaway hit, and the Flamingo was the only show in town during the middle of the week for quite a few months.

“Mr. Las Vegas” began investing his money, buying partial ownership of the Aladdin Hotel and helping to attract big name entertainment there, shrewdly scheduling those shows at off times in order not to compete with his own act. When other big names saw his success, they came to town for long term booking engagements as well; entertainers like Louis Prima, Liberace and the members of the Rat Pack (Frank Sinatra, Dean Martin, Sammy Davis Jr. and Joey Bishop).

And though Newton was a brilliant entertainer (and still is, he continues to play to sold out shows in Las Vegas to this day), he was not the best investor. He knew a good thing when he saw it, but when that thing turned bad, he would routinely invest more money instead of withdrawing from the deal. Gradually, more money began going out than coming in, and in his enthusiasm, Newton increased his investments, convinced he just needed to get the properties just right, or book just the right entertainment, and his investments would eventually pay off.

Then things took a turn for the worse. In 1980, Newton was profiled by NBC News as having ties to the mafia. While it was true that some mafia figures were invested in some of the same properties Newton had his own investments tied up in, it was never proven that he actually knew who the other investors were. Furious, he sued the NBC network for libel and the subsequent trial was long and very costly.

In 1992, Wayne Newton was forced to file for bankruptcy. In addition to the bad investments and worse publicity, Las Vegas had begun to change. The era of the “mega-casino” had arrived, and properties like the Aladdin and the Flamingo soon became antiquated in the new Vegas.

Wayne Newton has since recovered from his financial difficulties, and we are certainly happy for him. We think he’s an excellent example of how bankruptcy doesn’t necessarily happen overnight, and in fact can sometimes sneak up on you unawares.