6 Times These Big Investors Probably Said 'Whoops!'

Not even the wealthiest, most successful investors are immune from trading blunders. Some of the most famous fund managers and investing gurus have dropped the ball and mistimed their buys and sells.

Here’s a look at six times top investors probably thought, "Whoops!"

1. Ackman And Valeant

Pershing Square Capital’s Bill Ackman has had a roller-coaster of success and failures in recent years. Perhaps no failure has been as highly publicized as his stake in Valeant Pharmaceuticals, which is now Bausch Health Companies Inc BHC.

Ackman reportedly first took his massive stake in Valeant back in 2015 at an average price of around $196 per share. He then defended the company as the share price tanked over the next two years before finally unloading his position in March 2017 at a price of around $11 per share. Ackman reportedly took a $3-billion loss on Valeant.

2. Einhorn's Miss

Geenlight Capital value investor David Einhorn disclosed a 27.1-million-share stake in solar power company SunEdison in January 2016 when the stock was trading at around $2.70. By the time Einhorn dumped 75% of his SunEdison stake in early 2016, the stock was trading at 32 cents pending a bankruptcy filing and delisting from the NYSE.

3. Buffett’s Kraft Blunder

Berkshire Hathaway, Inc. (NYSE: BRK-A) (NYSE: BRK-B) CEO Warren Buffett is, in the eyes of many, the greatest investor of all time. Yet even Buffett isn't immune to being blindsided by the market.

Earlier this year, Buffett’s stake in Kraft Heinz Co KHC dropped by $4.4 billion when the food giant reported disappointing fourth-quarter earnings, slashed its dividend and disclosed an SEC accounting investigation.

Buffett’s 2019 losses come after the value of his Kraft stake dropped by $11.3 billion in 2018 as well. Despite the losses, so far Buffett has said he's sticking to his long-term holding strategy with Kraft Heinz.

4. Cuban’s Wild Netflix Ride

Billionaire investor, entrepreneur and "Shark Tank" personality Mark Cuban took a huge hit on Netflix, Inc. NFLX back in July 2016 when the company reported a big subscriber miss and the stock tanked 15% in a single day.

At the time, Cuban told Benzinga he wasn't concerned about the long-term outlook for the company.

"I'm not worried about quarter-to-quarter fluctuations," Cuban said at the time. "They continue to dominate the content and consumer delivery for over the top."

Cuban was ultimately proven correct, however, when the stock rallied 279% over the next two years.

5. Oop!

Earlier this year, Oprah Winfrey took a $46-million one-day hit to her Weight Watchers International, Inc. WW holdings when the company’s weak fourth-quarter report triggered a 30% sell-off.

Despite the big hit, Winfrey’s overall position is still significantly positive. Winfrey reportedly acquired 6.4 million shares of Weight Watchers back in 2015 at a price of $6.79. Weight Watchers shares trade around $19.28 as of July 1.

6. Dorsey's Double Dip

In the past three years, Twitter, Inc. TWTR shares are up 112% and Square Inc SQ shares are up 707%, generating obscene profits for the companies’ CEO Jack Dorsey.

But it hasn’t always been smooth sailing for Dorsey’s investments. During a two-week stretch back in 2016, Dorsey took a $355-million hit when both Square and Twitter reported disappointing earnings in the same quarter.

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