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.)

Two Rocks and a (Could Have Been) $17 Billion Family Legacy

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.

A $75 Million Marital Mistake

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.)

A $54 Million Hand-Motion Markdown

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.)

Stop That $4 Million Cab!

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.

What?! Call That $2 Million Foul, Ref!

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.)

The $1.5 Million Ferrari Fiasco

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.
Related Articles
  1. Retirement

    How Are 401(k) Withdrawals Taxed for Nonresidents?

    As a U.S. nonresident, deciding what to do with your 401(k) after you return home comes down to which tax penalties, if any, you're willing to incur.
  2. Mutual Funds & ETFs

    Top 3 Japanese Bond ETFs

    Learn about the top three exchange-traded funds (ETFs) that invest in sovereign and corporate bonds issued by developed countries, including Japan.
  3. Taxes

    Here's How to Deduct Your Stock Losses From Your Tax Bill

    Learn the proper procedure for deducting stock investing losses, and get some tips on how to strategically take losses to lower your income tax bill.
  4. Mutual Funds & ETFs

    What Exactly Are Arbitrage Mutual Funds?

    Learn about arbitrage funds and how this type of investment generates profits by taking advantage of price differentials between the cash and futures markets.
  5. Savings

    Become Your Own Financial Advisor

    If you have some financial know-how, you don’t have to hire someone to advise you on investments. This tutorial will help you set goals – and get started.
  6. Retirement

    Why Some Celebs Say 'No Inheritance for My Kids'

    To some of the super rich, inherited wealth is not the ultimate gift, it's a burden. Here's how their children—as well as charities—stand to benefit.
  7. Stock Analysis

    3 Solar Stocks to Add to Your Portfolio

    Understand the growth and challenges of the renewable energy market and its success in 2015. Learn about the top three energy stocks to add to a portfolio.
  8. Professionals

    How to Sell Mutual Funds to Your Clients

    Learn about the various talking points you should cover when discussing mutual funds with clients and how explaining their benefits can help you close the sale.
  9. Mutual Funds & ETFs

    Top Three Transportation ETFs

    These three transportation funds attract the majority of sector volume.
  10. Investing Basics

    Statistical Proof That Buy-and-Hold Investing Pays Off

    Learn about how the data suggests that the buy-and-hold investment strategy still works, even after the huge declines of the Great Recession.

You May Also Like

Trading Center
You are using adblocking software

Want access to all of Investopedia? Add us to your “whitelist”
so you'll never miss a feature!