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Countdown: The five WORST CEOs working today

Eddie Lampert, Sears Holdings (SHLD)

As you know, Eddie Lampert was a successful hedge fund manager, and he might still be one today, had not decided that, being successful, he must be brilliant, and being brilliant at hedge fund managing—which is, you know, complicated—he must necessarily be brilliant at managing a chain of retain stores, because that’s obviously simple. The spectacular downfall of Sears and Kmart, punctuated only by the selling off of assets and slowed only by loans from Lampert’s hedge fund, has been one of the most bizarre stories of the decade. I have been following the story closely, reporting, from time to time, on the occasionally hilarious slow-motion disintegration of my own neighborhood K-Mart, but that, alas, is over, for my neighborhood K-Mart, a landmark in my home town since my childhood, is now shuttered and boarded up. Thanks a lot, Eddie.

And I promised you dorky, so here’s yet another facet of the story. Eddie Lampert is said to have run K-Mart and Sears in keeping with his interpretation of the writings of Ayn Rand. Rand’s books often create a comical effect in readers, as they separate the world into the mass of people—mere sheep, and the special elect few few great souls upon whom everything depends. The comedy comes in because Rand’s works seem to whisper to everyone who reads them, Mr. Rogers style, that they are the ones who are special. To see someone adopt the view the he or she is a great soul and everyone else is a sheep… well, it’s tedious but forgivable in a college kid, but in a CEO?

Apparently nowhere in the work of Ayn Rand does it suggest that great souls out to know what-the-**** they are doing before they try to do it, though I suppose if it had, it wouldn’t have been nearly so inspiring to a man like Eddie Lampert.

SHLD

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Julian Close

Julian Close became a stockbroker in 1995. In his 20 years of market experience, he has seen all market conditions and written about every aspect of investing. Julian has also written extensively on corporate best practices and even written reports for the United Nations. He graduated from Davidson College in 1993 and received a Master of Arts in Teaching from Mary Baldwin College in 2011. You can see closing trades for all Julian's long and short positions and track his long term performance via twitter: @JulianClose_MIC.