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.

Jeffrey Skilling was the poster boy for corporate deceit before poster boys for corporate deceit were in vogue.

Now the Supreme Court is going to reconsider his 2006 conviction on charges that fraud by him and other top executives destroyed the world’s then-largest energy trader, wiping out pensions and employees’ life savings in the process.

Mr. Skilling has long alleged that he didn't know about Enron's shoddy accounting practices and risky business deals. He claims he didn't dump his shares of Enron stock and step down days before the company's collapse because he wanted to get out while the getting was good.

The scale of Enron's losses would seem to guarantee Skilling a place in the pantheon of bad bosses. Sadly, he has a lot of company. Here are five qualities that make a bad boss — and real-world examples of what to avoid.

1. Looking Out For No. 1

After rocketing to the mayor's seat in Detroit at the age of 31, Kwame Kilpatrick allegedly threw raucous parties at the mayor's mansion, charged thousands to city credit cards, and was accused of blocking a murder investigation. He really got into hot water in a salacious text messaging scandal. Ultimately, the mayor's legal missteps cost the city $9 million. Now, after 99 days in jail, the man once known as the hip-hop mayor told a Detroit judge that he had only $6 per month to pay back the $1 million in restitution he was ordered to pay due to the text message scandal. Then he moved into a rented million-dollar mansion in Southlake, Texas.

Honorable Mention: Enron's Skilling and Andrew Fastow.

2. No sense of limits

Wallace Souza, a Brazilian TV personality, disappeared last week after a warrant was issued for his arrest. Authorities say they believe he and his son used contract killers to commit grisly murders in order to boost ratings for his TV show about crime victims. Mr. Souza denied the charges before disappearing. His son is in custody on homicide and other charges.

3. Profoundly insecure

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."

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.