What Conrad Black and Bernie Madoff have in common

June 27, 2011, 8:14 PM UTC

Clarification, December 1: This June 27, 2011 article on Fortune.com entitled “What Conrad Black and Bernie Madoff Have in Common” referred to recent court proceedings involving Mr. Black. In July 2007, Mr. Black was sentenced to 78 months in federal prison after being convicted in U.S. District Court of three counts of mail fraud and one count of obstruction. After Mr. Black served 29 months, an appellate court threw out two of the fraud convictions and in June of this year his earlier sentence was reduced to 42 months, including time served. At no time was Mr. Black charged with, or convicted of, theft. Fortune.com apologizes for any confusion.

FORTUNE — Conrad Black was sent back to jail for another year on Friday. He deserves it, if not more.

Conrad Black, back to jail.

I have always considered Conrad’s fall a great tragedy—an otherwise brilliant man undone by greed and a spendthrift wife. He was smart enough to be beyond petty thievery, but his sense of self-importance apparently got the best of him, and he decided that the media company Hollinger, a public company, was his to plunder. Black was originally sentenced to 42 months for fraud and obstruction of justice and served 29 months, which means he could serve up to 13 more months. His delusions haven’t faded with time in the slammer, either: He’s so arrogant that he thought it worth people’s time to go on about “corporate governance zealots” during his sentencing hearing. And he once again suggested that David Radler, his sidekick at Hollinger, was the real brains of the fraud. Conrad was duped, you see.

I ran into Black in Palm Beach a few years ago. I asked him how he was—he was on his way to jail—and he was remarkably gracious, considering how a 2004 piece I’d written in Vanity Fair had been pretty vicious. He later sent me an email decrying not only my poor journalistic skills but also the utter destruction of Hollinger in the wake of charges against him. The fault for that, he said, should not be laid at his own feet, but at those of Richard Breeden, the former chairman of the SEC, brought in to investigate Black and Radler. Breeden had been made advisor to a special committee of Hollinger’s board, and proceeded to empty the company’s treasury investigating its former chairman and CEO.

Breeden coined a memorable term in his main report—he referred to Hollinger as a “corporate kleptocracy” run for the benefit of Black and Radler and no one else. But you could look at it in another way, which was that the Breeden managed to run an investigation not for the public good but for his own benefit. Black says Breeden sucked the life (and money) out of the struggling newspaper company, a crime he sees as far bigger than his own inability to keep his hand out of the corporate till. And he may have a point: Black and Radler were helping themselves to corporate assets, but during Breeden’s tenure, Hollinger effectively fell apart. Breeden went on to use his enhanced reputation as a man hard on crime to raise $1 billion for a corporate governance-focused hedge fund. Breeden did not respond to a request for comment. (For more on the idea of the detective who is guiltier than the criminal himself, go read the work of Conrad Black apologist Mark Steyn on the subject.)

The Madoff mirror effect

On the same day that Black was resentenced, Irving Picard, the trustee liquidating Bernie Madoff’s bogus hedge fund, filed an updated claim against JPMorgan Chase accusing it of complicity in the Madoff fraud. Picard issued a press release upping his demands of disgorgement from the big bank from $5.4 billion to $19 billion. This is the same man who essentially forced the New York Mets into the hands of hedge funder David Einhorn by loudly and publicly accusing Mets owner Fred Wilpon of willful ignorance of Madoff’s fraud. Picard is accusing both Wilpon and JPMorgan Chase (JPM) of the same thing, which is allowing a fraud to continue because it was too profitable not to. He may be exactly right in both cases. On the other hand, his methods have taken on an overly dramatic aspect.

The two different stories share a common theme. While I am not one to suggest denying anything to the defrauded, shouldn’t there be more checks and balances of people in trustee/investigative positions? According to a recent filing, Picard’s billings in the Madoff debacle are fast approaching $200 million. That’s about the same Hollinger spent investigating itself via Breeden. Of course, Picard has already recovered billions of dollars for Madoff investors—including $7.2 billion from the estate of Jeffrey Picower alone. So dollars-for-dollars, he’s been worth many multiples of his expenses. The same cannot be said for Breeden in the case of Hollinger.

Picard is crafty – he doesn’t do a whole lot of on-the-record interviews, but most journalists take his accusations against people like Wilpon and JPMorgan Chase as gospel truth. Maybe the cheering in the press has gone to his head, and he’s somehow decided that over-the-top public accusation is a more effective strategy than pressure-and-persuade. This latest move by Picard didn’t get him any closer to a settlement with JPMorgan Chase, if that was even a possibility in the first place.

Could Picard have motives that aren’t as noble as making defrauded investors whole? Perhaps that he is milking this thing for all he can get? There’s nothing wrong with taking advantage of opportunity, but the common thread between Breeden and Picard is that both are, in effect, big beneficiaries of their own investigations.

It doesn’t have to be this way: Enron was the largest bankruptcy in American history at the time of its failure, but its unwinding didn’t waste a meaningful amount of money. But maybe Enron is the exception. The Lehman Brothers bankruptcy, for example, has turned into a sort of transatlantic legalistic orgy. Sure, some creditors get the shaft—that always happens when people are arguing over a pile of money smaller than it is supposed to be—but I honestly thought it was just a well-worn joke that the lawyers are the big winners in these situations. Is it actually true?

I recently wrote that Picard deserved a Pulitzer for the potboiler-like writing in his legal filings in the Madoff case. I’m thinking he might deserve an Oscar, too. It’s been one hell of a public performance.