6 Biggest Millionaire Flops

Portfolio losses got you down? That's understandable. The dramatic 2008 market drop-off caused the S&P 500 Index to tumble 37%, wiping out more than $4 trillion in workers' retirement plan savings alone.

If you lost money, you're not alone, but at least you can put some blame on the market. Major errors of judgment have cost some of the world's richest people more than just a pretty penny - and these are people who have a lot to lose. Console yourself with these famous financial flops. (Want to be a millionaire yourself? Read Getting A Millionaire's Mindset.)

In 1883, Dr. William Howey went to check on crews building the Canadian Pacific Railway. While searching for a lost worker, he found some interesting copper-colored rocks and pocketed them. Upon returning home he sent them to the director of the Geological Survey of Canada. The verdict? The stones were deemed worthless, and Howey threw them away.

A contractor picked them up, and a year later decided to check out the site where they were found. It turned out those "rocks" were copper and the contractor - Thomas Murray - had discovered one of the world's largest copper deposit, producing millions of dollars of ore.

Madonna may have a knack for putting out hit records, but her most recent divorce to film director Guy Ritchie will hit the "material girl" where it really counts - the wallet. Why? No prenuptial agreement. The 25-time gold record winner will pay her ex-better half $75 million as part of their divorce settlement. That equates to just a little less than $10 million for each year of their eight-year marriage. Don't feel too bad for the pop and rock icon, however - she's still worth more than $400 million. (Don't make this mistake. Read Marriage, Divorce And The Dotted Line to learn how to set up your own prenup.)

Vegas casino owner and art collector Steve Wynn was entertaining a small group of friends in the fall of 2006 when he decided to show them his prized Picasso "Le Reve," ("The Dream"). He had recently agreed to sell the piece for $139 million to fellow collector and hedge fund director Steve Cohen.

But Wynn's "dream" turned into a nightmare when, with one seemingly harmless hand motion while hosting a party at his home, he put his elbow through the famous painting of Picasso's mistress. It cost Wynn $90 million ($5 million more than it was now worth) for restoration work. (A sound insurance policy could have saved the day. Read The importance Of Property Insurance.)

In 2008, Russian violinist Philippe Quint left a $4 million 1723 Antonio Stardivari violin in the back of a taxi after a ride home from Newark Airport. There are fewer than 700 of the handmade, highly-prized instruments worldwide.

Six frantic hours after reporting the loss, Quint got a call from the port authority that driver Mohamad Khalil had returned to the station with his instrument. When the two met, Quint fell to his knees in thanks; to demonstrate the depth of his gratitude Quint later treated Khalil and 200 of his cabbie-driving comrades to a 30-minute private concert at the airport.

Wimbledon champion and TV commentator John McEnroe wouldn't let an opponent get away with anything on the tennis court, but a high-flying rare art salesman got away with $2 million of McEnroe's fortune. Lawrence Salander, a New York art dealer, defrauded McEnroe through an elaborate scam by selling him half-shares in painter Arshile Gorky's pieces "Pirate I" and "Pirate II." One slight detail the dealer forgot to divulge: he didn't own the paintings. (Want to try your hand at investing in collectibles? See Fine Art Can Be A Fine Investment.)

Actor Eddie Griffin had the best of intentions when he signed up to drive a $1.5 million Enzo Ferrari for a charity benefit and to promote his 2007 movie "Redline," in the process. Just moments after taking the wheel, Griffin took a corner a little too tight, clipped a cone and locked the wheels of the prized car, slamming it into a concrete barrier. Although he walked away unharmed, the rare car was declared a total loss.

Could it get any worse? Actually, yes. The car was owned by Griffin's boss, "Redline" executive producer Daniel Sadek.