If your investment returns in 2014 tracked the stock market, you’d be up a respectable 8% for the year so far. If you bet big on one of several high-flying IPOs, such as Alibaba (BABA), GoPro (GPRO) or Lending Club (LC), you did a lot better.

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But big personalities tend to take big risks, and sometimes they end up a lot worse off than the average Joe. Here are 10 people who lost big in 2014:

Harold Hamm

This former wildcatter is one of the fracking leaders guiding the United States toward energy independence -- yet the markets have punished Hamm lately. The oil glut has pushed shares of Hamm's firm, Continental Resources (CLR), down 44% this year, and since Hamm owns 253 million shares, or about 69% of the firm, the value of his stake has fallen by some $6.2 billion. In November, a judge also ordered Hamm to pay his ex-wife Sue Ann $1 billion in a divorce settlement. That leaves Hamm down $7 billion or so.

Jeff Bezos

He may have saved a storied outpost of journalism by purchasing The Washington Post earlier this year, but the source of Bezos' wealth -- Amazon.com (AMZN) -- suffered a steep 23% drop in its stock price in 2014. Amazon is still a leader in online retail, but big chains such as Walmart (WMT) and Target (TGT) are catching up, and Amazon's Fire phone was a flop. Since Bezos owns about 84 million shares of Amazon, roughly 18% of the company, the stock's slide cost him more than $7.5 billion. But don't worry: Bezos still has at least $25 billion.

Vince McMahon

World Wrestling Entertainment (WWE), which McMahon founded and leads as CEO, has been on and off the mat this year, with the stock surging early in 2014 on big hopes for a new streaming network, then plunging as the streaming plan and other TV deals turned out to be disappointing. The brash McMahon, who owns nearly half of all WWE shares, briefly became a Forbes billionaire in January, but lost $500 million or more as the shares plunged a few months later.

Ray Rice

The former star running back for the Baltimore Ravens lost about $10 million in pay for the next three years when the NFL banned him indefinitely following the release of a videotape showing him hitting his wife in a hotel elevator. Rice has now been reinstated, and he's free to sign with another team for whatever he can get. But his two corporate sponsors, EA Sports and Nike, both canceled their contracts with him, thought to cost Rice about $1.6 million per year. He may never regain stardom or attract another corporate sponsor.

Mark Karpeles

The former CEO of Mt. Gox achieved digital infamy in February when the bitcoin exchange went bankrupt and roughly 850,000 bitcoin belonging to depositors—equivalent to about $450 million—vanished. Karpeles owned 88% of Mt. Gox, which lost around 100,000 of its own bitcoin, or more than $50 million. Investigators in Japan, where Mt. Gox was based, are still trying to determine if the cause of the losses was fraud, theft, mismanagement or something else. Whatever it turns out to be, bitcoin was a terrible investment in 2014 even if you kept all your holdings, with the value falling by 54% since the start of the year.

Mikhail Prokhorov

The owner of the Brooklyn Nets may be the most nonchalant money loser of 2014. "It's not a big deal," he explained when asked about the $144 million his NBA team reportedly lost during the playing season that concluded last spring. Prokhorov spent lavishly to attract top players, even paying an $82 million luxury tax to the NBA for exceeding payroll caps. The result: An unsatisfying departure in the second round of the 2014 playoffs. But there's more where that came from. Prokhorov, a Russian investor, is worth around $9 billion, according to Forbes.

Vladimir Putin

Russia's leader is probably one of the world's wealthiest men, but he's taking a pounding as the Russian ruble plummets and the economy he manages rapidly deteriorates. As a huge oil producer, Russia is reeling from the 45% drop in crude prices since the summer. Western sanctions leveled against Russia for its role in Ukraine's civil war are compounding the pain. Putin can surely withstand the financial losses, which are hard to measure since his holdings are secret. The bigger question is whether he can maintain his usually airtight grip on political power.

Steve Wynn

A sweeping Chinese anti-corruption probe has sent Wynn Resorts' (WYNN) stock into a swoon, with shares down 25% so far this year. The casino operator earns much of its revenue from Macau -- the Las Vegas of China -- where gambling revenues have tumbled as high rollers stay home and authorities guard against the outbreak of Hong Kong-style democracy protests. Since company co-founder and CEO Wynn owns about 10% of the stock, his net worth has fallen by around $500 million this year. His ex-wife Elaine owns nearly as many shares and therefore has lost nearly as much.

John Mackey

The Whole Foods (WFM) CEO earns just $1 per year in salary, plus a bonus, if it applies. This year, it may not. The grocery chain's stock is down 16%, which hurts Mackey along with other shareholders. He owns nearly 1 million shares of Whole Foods, more than any other individual, with the value of his stake down by an estimated $10 million this year.

Courtney Love

The grunge rocker confessed this year that she lost roughly $27 million following the 1994 death of her husband Kurt Cobain, frontman for Nirvana. Most of the money evaporated amid legal battles. But life goes on. "I know that's a lifetime of money to most people, but it's rock 'n' roll,” Love explained. "I had to let it go."

Rick Newman’s latest book is Rebounders: How Winners Pivot From Setback To Success. Follow him on Twitter: @rickjnewman.

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