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The New Economy

Is Jeffrey Skilling the worst boss ever?

Jeffrey Skilling will get a Supreme Court hearing. Could any bosses be worse than the ex-Enron chief? Here's five.

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While A.I.G. Financial Products issued a kind of insurance on a growing mountain of toxic subprime mortgage securities that brought its parent company – and, some would say, the global financial system – to the brink of collapse, the unit's CEO, Joe Cassano, was bullying employees and exploding at any perceived criticism, according to a profile in Vanity Fair. "He entertained a notion of himself as the street-smart guy who had triumphed over his social betters—which of course implied that he wasn’t quite sure that he had," wrote author Michael Lewis, as he describes how Mr. Cassano's missteps and misjudgments led to the unit's huge losses. "Even by the standards of Wall Street villains, whose character flaws wind up being exaggerated to fit the crime, Cassano was a cartoon despot."

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4. Deceiving

Even if he's a tough guy in the poke, Bernie Madoff made his prison bed by conning stars like Steven Spielberg and New York Mets owner Fred Wilpon (among a host of others) with his financial background and low-key charm. If would-be investors pressed him about his system, he was not terribly forthcoming. But his apparent investing record – consistent annual returns of 12 percent or better – was so compelling that even careful financial experts who decided not to invest with him wondered if they'd made a big mistake. It turns out they were the smart ones.

5. Tyrannical

As CEO of Colonial Bank, Bobby Lowder clung to bad Florida mortgages until the bitter end, leading to a collapse that was the largest bank failure in 2009 and the sixth-biggest in US history. A domineering personality, he engineered one coaching coup and almost succeeding in another at his beloved Auburn University. He's not college sports' most powerful booster by accident. A profile this week from Fortune included this incident while Mr. Lowder headed Colonial:

In 2004, Montgomery got a new minor-league baseball team called the Biscuits. A Colonial marketing executive bought a few season tickets to use with clients. A few days later, while on a business trip, he got a call from his boss. She asked whether he'd bought Biscuits tickets, and when he said yes, she told him to return to Montgomery. "Will I have a job when I get there?" he asked. "No," was the response. Mr. Lowder, he was told later, didn't like the Biscuits.

David Grant is a Monitor contributor.

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