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The Globe and Mail

Steve Ballmer's best blunders at Microsoft

EMMANUEL DUNAND/The Globe and Mail

Why is Microsoft CEO Steve Ballmer on the hot seat? Maybe it's the meandering trail of missteps that got him there.

Let's consider the humble Windows Vista fiasco, the failed Yahoo takeover, maybe the recent Skype Hail Mary, and who can forget the Windows Mobile massacre?

The stock tells the story well. After reaching a high of $35.55 (U.S.) a decade ago, Microsoft shares have been dead money. For one of the most widely held and heavily traded stocks in the market, investors have been unusually patient with the dismal performance.

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But the cry for new leadership at Microsoft is starting to get louder now that stakeholder Greenlight Capital's David Einhorn has placed a bull's-eye on Mr. Ballmer's back. Mr. Einhorn's famous "Lehman is doomed" prophecy makes him a highly qualified heckler, but since Lehman, Mr. Einhorn has had a mixed record on predictions -- Sprint has done well; the jury is out on the Mets, but Yahoo has been a bust recently.

Mr. Einhorn, however, is the loudest voice yet calling for Mr. Ballmer's ouster, and barring some radical change of fortune for Microsoft, the chorus will get louder.

To be sure, Microsoft has had victories during Mr. Ballmer's 11-year run as CEO -- Windows 7 and Xbox to mention two -- but it's the spectacular failures that stand out at times like these.

No. 1: Windows Mobile

Under the heading of the big one that got away, Microsoft's Windows Mobile was one of the leading smart phone operating systems of the past decade. It was a natural but way too bulky extension of the Windows PC franchise and the key to Microsoft's expansion beyond desktops.

But along came Apple and Google's Android, and without an immediate answer, the Windows Mobile opportunity slammed shut. Windows Phone 7 has had a very difficult time making up for the lost ground in smart phones so far.

No. 2: Windows Vista

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Apple owes a good part of its great fortune to Microsoft, if for no other reason than the Vista PC operating system. Computer buyers were faced with a decision to buy a Vista machine or convert to Apple. It was a no-brainer for many who abandoned Microsoft and never looked back.

No. 3: Yahoo

Merger negotiations have rarely been as awful and acrimonious as the run or runs that Microsoft made at Yahoo.

Mr. Ballmer couldn't hide his contempt for Yahoo even as he upped his bid to acquire the company. And Yahoo, ignoring its big shareholders like Carl Ichan, found Microsoft so distasteful it preferred to stay on its own road to ruin.

No. 4: Skype

Microsoft sits on $50-billion in cash and investments -- that's shareholders' money as much as Microsoft's. So when Microsoft, out of sheer desperation, decided it would write an $8-billion check for the Net-calling shop Skype earlier this month, investors may have had enough.

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The merits of the Skype move are sound, a working Internet business model that Microsoft has had great difficulty creating on its own. But it may prove to be too far afield from the software giant's core strength and yet another distraction.

And it may go down as Mr. Ballmer's last big move.

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