Conrad Black was CEO of Hollinger International, a media company. Black stacked his board with influential neo-conservatives like Henry Kissinger and used its cash to finance his personal life.

He is one of the most arrogant people I've never met. I heard a radio interview he did a few weeks ago in which he dismissed all the charges against him as completely unfounded and trivial. But the judge in his case did not agree -- sending Black to jail for six-and-a-half years and making him pay $6.1 million -- the amount he stole from Hollinger.

Interestingly, Black could have saved himself from jail. According to Sunday Herald, in 2003, he signed an agreement to pay $7.2 million to settle charges that he defrauded Hollinger. Without Hollinger board approval Black took non-compete payments then sold off newspapers to Horizon, his private company, using phoney valuations to pay off the $1.9 billion Hollinger owed in 1998.

It would not have surprised me if he had tried to use his ties to neoconservatives to get the government to back off from its prosecution. But given that government's unpopularity, it could not afford to be seen helping this pompous kleptocrat.

Be sure to check out other Money Losers of 2007.

And you thought that the 2006 Home Depot (NYSE: HD) annual meeting showed a lack of respect and contempt for shareholders. Jurors in the trial of disgraced former Hollinger International CEO Conrad Black heard some choice comments from that company's 2002 and 2003 annual meetings. He told one disgruntled shareholder that "We haven't been sitting here and feathering our nests." Well, that turned out to be true. They were extremely busy... looting the company and committing fraud.

In emails that Black wrote during 2002, he referred to the shareholder revolt as an "epidemic of shareholder idiocy" and said that he wanted to "blow their asses off."

It's interesting that one of the common threads among so many of the embattled former titans of industry is arrogance and a disdain for shareholders and critics -- Jeff Skilling called a hedge fund manager on a conference call an "a-hole" after the man raised eerily prescient questions about the company's balance sheet.

I think there's a reason for this pattern of behavior. When faced with tough questions, reasonable people who are right can simply explain the situation to investors and hopefully win them over with a logical argument. Of course, when your critics are right, you can't do that. You have no choice but to launch into personal attacks and other diversionary tactics.

The lesson here for shareholders is this: When a CEO is testy with shareholders who raise questions about the company or, even worse, blames short-sellers or hedge funds for their lagging performance, you may want to sell the stock.