5. Bruce's Promised Land
No, not the medical device company! We're talking about St. Jude, the patron saint of lost causes, because that's what his investment in the Florida land bank is starting to look like.
St. Joe announced last Friday that it's reached an agreement allowing its largest shareholder, Berkowitz's Fairholme Capital, to buy up to 50% of its shares, sending the stock up more than 6% as a result. Fairholme currently owns about 29% of the company's stock and Berkowitz is St. Joe's chairman, a title he nabbed in March after ousting the company's board over its spending habits.Judging by Berkowitz's recent tendency to throw good money after his own bad bets, he clearly has a spending problem of his own. Shares of St. Joe have lost 17% year-to-date, and more than 25% since hedge fund assassin David Einhorn -- yes, he who called Lehman's demise but recently struck out trying to buy the equally hapless New York Mets -- named the company as his favorite short in a skewering presentation last October. Nevertheless, Berkowitz has continued to gobble up more and more shares of this turkey even as it dives lower and lower. To be honest, we're starting to wonder if he wants to quit his job as a stock picker and start a new career as a full-time real estate developer. And it's not just St. Joe where Berkowitz is throwing Hail Mary passes. He's using the same go-for-broke strategy with other broken-down stocks such as Bank of America (BAC - Get Report), AIG (AIG - Get Report) and Sears Holdings (SHLD). As a result, Berkowitz, who was hailed as Morningstar's equity fund manager of the decade in 2010, has seen billions in outflows from his $11 billion Fairholme Fund (FAIRX), now down over 24% for the year, putting it in the 99th percentile for large value funds tracked by Morningstar. Over the past decade, however, the fund has returned an annual average of more than 8%, which puts it in the top 1% for the time period. And it's that long-term track record which makes us want to write off Berkowitz's knife-catching spree as a bout of temporary insanity and not a full on death wish. That said, if he continues down this path and keeps raising his interest in St. Joe, where the value of its 574,000 Northern Florida acres is hotly disputed, it will get harder and harder to view Berkowitz as a brilliant value manager having a bad year, rather than a false prophet leading his followers into a money-losing heaven.