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I-Cahn’t Quit You (Without Losing a Bundle in Yahoo Shares)

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Champagne wishes and caviar dreams are now but a memory for billionaire shareholder-activist Carl Icahn, who lost about $125 million today by selling off 16 percent of his ever-losing stake in Yahoo.

The sale of 12.7 million shares at just under $15 a piece is a far cry from the hopes that the famously prickly Icahn had when he started his quest to bring about change and riches for himself by investing in the stock of the turmoil-plagued Internet giant in 2008.

Icahn went far in waging a proxy fight for control of the Yahoo (YHOO) board.

He got on the board all right, along with nabbing two other seats, but that’s about all he got.

No $40-billion-plus sale to Microsoft (MSFT), a much lesser search deal and yet another troubled investment for Icahn in a year of troubled investments.

As it turned out, he came to Silicon Valley, he saw, he did not conquer.

Nonetheless, Icahn still has a 4.5 percent stake in Yahoo, or about 63 million shares.

In a filing with the Securities and Exchange Commission, Icahn said the move was to balance his portfolio, but that he still was bullish on Yahoo, its recent search deal with Microsoft and Yahoo CEO Carol Bartz.

Which is also rich, given that she just dissed him again publicly in a piece in Forbes, tossing off a saucy insult:

“Icahn is just another shareholder. What’s he going to do, fire me?”

Well, in a tiny little step today, he kind of did that to Yahoo.

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  • david vanvoorhis
    It is certainly hard to believe that the Yahoo management thinks this was really such a great "deal" seeing how they dumped their stock as it was being negotiated. Most investors including Icahn expected a sale to form a strategic partnership against google and then Yahoo was given away for free.
  • I think every one forgot about when he purchased 6,778,804 shares average at $9.92 from November 24th through 26th last year http://online.barrons.com/article/SB12277445996... I don't think he lost the amount of money that we think he lost
  • A:

    He has to hold those shares longer to get the tax benefit. True, he bought some at a lower price, but Icahn has had a bath in Yahoo in general.
  • D:

    I think Icahn, as a board member, was fully informed as to the deal and signed off on it.
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Kara Swisher started covering digital issues for The Wall Street Journal's San Francisco bureau in 1997 and also wrote the BoomTown column about the sector. With Walt Mossberg, she co-produces and co-hosts D: All Things Digital, a major high-tech and media conference. Read more »

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