Money Losers of 2007: Eddie Lampert's year in review

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Eddie Lampert So how does Eddie Lampert, chairman of Sears Holdings (NASDAQ: SHLD), with his stellar track record as a hedge fund manager, the man behind the 2005 merger of Sears Roebuck and Kmart merger -- how does he end up as a Money Loser of 2007?

Things looked bright at the beginning of the year as Lampert was hailed as the next Warren Buffett, and Sears Holdings was seen as developing in the mold of Berkshire Hathaway (NYSE: BRK.A). Lampert was a long-time favorite of Jim Cramer, who early in the year felt that Sears was a better investment than Wal-Mart (NYSE: WMT).

Investors and watchers waiting for the Lampert magic to happen were puzzled by his interest in Citigroup (NYSE:C), though that interest did benefit Citigroup at the time. But as Sears' first quarter results showed sales further slumping, investors grew impatient.

Even as Lampert called for $5 billion in cash in early summer, a visit to Sears stores showed an enterprise badly in need of a face-lift. Sears was lagging further behind other retailers, and the share price was sliding from a 52-week high in April. It grew increasingly clear that Lampert was neglecting the retail side of the business. Sears warned not to expect much in the second quarter.

Sears began buying back shares late in the summer, seeming to confirm that Sears, and Lampert, were struggling. Dismal second quarter results only added to that impression. In a head-to-head face-off between Eddie Lampert and Warren Buffett here on BloggingStocks, readers overwhelming voted for Buffett as the more money savvy. So much for the pupil besting the master.

As autumn rolled along, Lampert faced increasing pressure to sell real estate, which had been seen as the strength of the Sears-Kmart merger. Shares continued to fall, attracting the attention of some bargain hunters, and reached a new 52-week low. Meanwhile, Citigroup took a big hit due to the mortgage meltdown, and so did Lampert's stake in it. On top of that, Sears third quarter results showed a 99 percent drop in profits year over year.

Criticism has continued to build, and rumors of a breakup of Sears Holding have swirled. Jim Cramer now sees Sears as being on par with Wal-Mart as an investment to avoid. Lampert lashed out at critics, which did nothing to help his case, of course.

The question is, is Lampert's neglect of the retail side of the business to focus on Sears as an investment vehicle a failure on his part? Not everyone thinks so. Even now, Lampert has his supporters.

Be sure to check out other Money Losers of 2007.

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Last updated: February 09, 2010: 03:30 PM

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