If you've ever read Deadline Hollywood or the columns of Art Buchwald you've been exposed to the clients of Pierce O'Donnell. The high-profile Los Angeles lawyer has represented both Buchwald and Deadline editor Nikki Fink against heavy hitters including Paramount, Disney, and News Corp. He also ran for Congress in the Glendale-Burbank-Pasadena area, and co-wrote a book, Fatal Subtraction: The Inside Story of Buchwald V. Paramount, about his representation of Buchwald. More recently, he represented victims of Hurricane Katrina in a lawsuit against the U.S. government. Now, he's probably going to jail.

O'Donnell is known as a tenacious litigator who goes up against the big boys. In 1988, he sued Paramount Pictures for $5 million on Buchwald's behalf, claiming the studio had ripped off the idea for Coming to America, the Eddie Murphy hit, from a treatment Buchwald had pitched six years earlier. Paramount settled out of court. That launched his high-profile career, during which he represented The Wire creator David Simon as he and Barry Levinson accused Warner Brothers of stealing details from Homicide to make a show called Polish Hill.* Later, he represented Faye Dunaway when she sued Andrew Lloyd Webber for firing her from Sunset Boulevard. O'Donnell's Hollywood resume stretches on and on. And given the number of high-power players he's worked for and protected, he's not the kind of guy you would expect to end up going to jail over $20,000 in campaign donations.

But O'Donnell has pleaded guilty to two misdemeanor campaign finance fraud charges, and has agreed to take six months in jail should a judge sentence him on Nov. 7. The mystery is why such a savvy litigator got involved in a scam so simple and easy to catch. Here's what he did in 2004, according to Friday's Los Angeles Times:

In a plea agreement with prosecutors, O'Donnell admitted to asking 10 people, including employees of his law firm and at least one relative, to each make donations of $2,000. He then reimbursed them, thereby masking that he was the source of the funds. The attorney agreed to serve six months in federal prison for the "conduit contribution" charges, in addition to a $20,000 fine and 200 hours of community service.

Reimbursing people for their campaign donations is a big, obvious Campaign Finance Law 101 no-no. So which politician inspired such ardor that the savvy legal mind would risk jail time to push his electoral chances? None other than John Edwards, who would go on to get the vice presidential nomination

The unlawful Edwards bundling was not the first time O'Donnell was accused of dodgy campaign contributions. He was accused of "reimbursing 22 employees and others for $25,500 in contributions to the 2001 mayoral campaign of [Los Angeles mayor] James K. Hahn, in violation of a $1,000 per person limit," according to The New York Times. In fact, it was news of those allegations that led Edwards to return $44,000 from a 2003 fundraiser O'Donnell organized. 

O'Donnell hasn't offered comment on the charges, but the crux of his defense team's arguments hinged not on whether he had committed the campaign finance fraud, but rather he was being singled out for prosecution. A Los Angeles Times story from 2008 reported that his team had "presented prosecutors with nearly two dozen illegal campaign contribution cases that they say were handled administratively by the Federal Elections Commission, even though most involved larger amounts of money and more egregious conduct than is alleged in O'Donnell's case." 

And that argument may have actually worked. At Politico, Josh Gerstein noted prosecutors were originally seeking a plea bargain that included a felony conviction, which would entail O'Donnell's losing his law license permanently (it is currently suspended). O'Donnell's defense team characterized the case as a victory because he pleaded guilty only to a misdemeanor, . "From the outset of this case, we have been seeking to get the charges reduced to misdemeanors," his lawyer, Brian J. O'Neill, told the Orange County Weekly. The U.S. Attorney prosecuting the case, André Birotte Jr., was more smug. "As an experienced attorney and former candidate for the United States Congress, Pierce O’Donnell should have been well aware of federal election laws concerning campaign contributions," he said in a statement. And, now, unless a judge intervenes in November, O'Donnell is headed to jail.

*Correction: This story previously incorrectly said that David Simon once sued Warner Bros. The 1992 dispute Simon and director Barry Levinson had with Warner Bros. was resolved before going to court, so it was incorrect to refer to it as a lawsuit.