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If corporate raider Carl Icahn ever had any hope of convincing major Yahoo shareholders like Legg Mason's Bill Miller to back his alternative slate against the Yahoo board in a proxy fight, he needed a plan B in case a sale to Microsoft didn't work out. As Kara Swisher puts it, he needed "a solid management team and a cogent plan." For two reasons: One, because without an alternative to a merger with Microsoft, Microsoft would own all the chips in any merger negotiations. Two, by not naming a replacement Yahoo management team, Icahn left major shareholders with the impression that he himself would control the company after winning a proxy fight. Shareholders are unhappy with Yang & Co., but they tell Swisher that "taking such a major step as dumping them and leaving the company in Icahn’s hands — even for a short time he will be there — is decidedly more risky." So if it was so important that he do so, why didn't Icahn ever name a nominee for Yang's job? Because he was caught in a classic Catch-22.

Why would respectable Web industry executives like former Yahoo COO Dan Rosensweig, former Fox Interactive boss Ross Levinsohn, or Levinsohn's partner at Velocity Interactive, ex-AOL CEO Jon Miller — the kind of names shareholders would trust — sign up with Icahn just in time to get replaced by Microsoft's Kevin Johnson? And why would they jinx their chances at a getting named to the plum job by Yang itself — a far more comfortable coronation? That's why those names never showed up in an Icahn press release. It's also why Icahn's board slate is filled by a bunch of no-names and Mark Cuban, whose feud with Yahoo is now nearing a decade in age.

So, what did Carl Icahn really do wrong? Buy his first share of Yahoo.

(Photoillustration by Jackson West; photo of Icahn by AP/Mark Lennihan)