Over 40 years, attorney Brendan V. Sullivan Jr. has had a career most of his peers would envy, representing the likes of Iran-Contra operative Oliver North, Alaska Sen. Ted Stevens, and the Duke lacrosse players accused of rape. And then there’s the one resume item none of his colleagues can match: Sullivan’s starring role in a 1992 pop song.

“He’s a prophet, he’s not just a lawyer,” Minneapolis band Beat the Clock croons on the eponymous “Brendan V,” a tribute to Sullivan’s talent at helping white-collar defendants dodge prison. “He’s a criminal, too.”

With thinning hair and tortoise-shell glasses, the 71-year-old Sullivan makes an unlikely rock muse. Now, as the attorney for embattled District mega-donor and alleged mayoral shadow campaign financier Jeffrey Thompson, Sullivan sits at the center of the federal investigation into the District’s politics.

That investigation may be taking U.S. Attorney Ron Machen a while, but he’s scored only wins so far in his drive to clean up the District. He’s bagged three former councilmembers and secured guilty pleas from people around Thompson, a former Medicaid contractor for the city. In the last three weeks alone, two former employees of Thompson’s and former At-Large Councilmember Michael Brown have signed statements implicating a man whose description matches Thompson (though he’s not named in the court papers) in campaign finance violations.

But despite Machen’s streak, Sullivan represents a serious threat, and not just to the U.S. attorney’s reputation. That’s because Sullivan goes after prosecutors as hard as they go after his clients. Attorneys who have tangled with him have lost cases, their licenses to practice law, and their freedom.

Sullivan developed his distaste for prosecutorial overreach while stationed in San Francisco during the Vietnam War. Even though Sullivan was in the Army as a supply officer, his law degree attracted attention from inmates at the Presidio stockade, who asked him to represent them in a protest of overcrowding. Sullivan won them an unlikely victory—and earned a transfer to Vietnam for his efforts. Though the Army canceled Sullivan’s move after public outcry, it left him distrustful of authority. Sullivan abandoned his dreams of running a Fortune 500 company and opted instead for law.

After he was discharged, a Georgetown law school professor introduced him to Edward Bennett Williams, a prominent defense attorney whose clients included Jimmy Hoffa and Joe McCarthy. Sullivan joined Williams’ tony Williams & Connolly law firm. At the firm, Sullivan would entice his new mentor to visit his office by offering Williams his beloved peanut butter crackers, according to a 2012 interview in Washingtonian.

Sullivan soon earned a reputation as a tough opponent. Representing a Maryland company on charges of tax evasions, he caught IRS agents backdating documents, a revelation that inspired a judge to call the government’s actions “patently egregious.” But Sullivan wasn’t above some tricks of his own—a 1987 Washington Post profile describes him posting an anti-smoking sign from the American Cancer Society around his office to unnerve witnesses who smoked during depositions.

Sullivan shot to national prominence in 1987, when he represented North in televised congressional hearings over the Iran-Contra scandal. When one senator asked him to stop interrupting North, Sullivan remarked that he wouldn’t be a “potted plant” in the proceedings. The rest of Sullivan’s representation was equally combative—at one point, he shouted down a question he felt violated attorney-client privilege: “That’s none of your business either!” (Sullivan’s actions in the North hearings were the inspiration for the song about him.)

From Iran-Contra, Sullivan went on to more prominent cases—and racked up a series of punishments for prosecutors. Sullivan represented three of the Duke lacrosse players accused of raping a stripper in 2006. He turned the case back on prosecutor Mike Nifong, who had held back DNA evidence that would have weakened his case. Nifong served a day in jail for contempt of court and was disbarred, and Sullivan’s clients were acquitted.

But Sullivan’s most prominent win against the government—and the one that must loom largest for the U.S. Attorney’s Office—came in another public corruption investigation. In 2008, a grand jury indicted Alaska Sen. Ted Stevens, a Republican, on charges of failing to report gifts. Stevens hired Sullivan to represent him but was nevertheless found guilty months later.

In 2009, though, an FBI agent revealed that prosecutors had held back information that would have contradicted one government witness. A judge held the prosecutors in contempt of court, calling their withholding “outrageous.” One, Nicholas A. Marsh, killed himself in 2010 during the investigation. Two others were suspended, although their punishments were overturned last April after a judge decided the punishments violated Justice Department procedures.

It’s hard to tell what accounts for Sullivan’s bruising record with prosecutors. Sullivan rarely talks to reporters, and he didn’t make an exception for LL. But in 2012, Sullivan explained his theory about the government to PBS interviewers for a special on overzealous prosecution, claiming that “the heat of battle” makes ordinarily honest prosecutors abandon their ethics. “Prosecutors see almost everyone they deal with as a law violator,” Sullivan said. “I call it the Al Capone mentality.”

While Thompson hasn’t been charged with any crimes, Sullivan is skilled enough with handling pending charges that he wrote the book on them—literally, with 1983’s Techniques for Dealing With Pending Criminal Charges or Criminal Investigations.

So far, Sullivan’s work on the Thompson case has taken place out of the public eye, in closed courtrooms and from his perch at Williams & Connolly. The FBI raided Thompson’s home and offices in March 2012, but Sullivan managed to file motions that tied up the 23 million pages worth of seized records for an entire year. An appeals court eventually ruled that the government could review the records, but Sullivan’s motions set the investigation back months. Even now, Machen won’t say publicly whether investigators have access to Thompson’s files.

Sullivan’s work likely doesn’t come cheap for Thompson. In 2010, Washingtonian estimated that the average Williams & Connolly partner made $1.18 million a year. “Who makes more?” the magazine asked rhetorically, responding with just one name. “Brendan Sullivan.”

Over the past year, Thompson has been engaged in a property sell-off that could be aimed, at least partly, at paying off whatever Sullivan’s “more” adds up to. Thompson has sold his Medicaid contracting firm and his shares in his accounting firm. Last year, Thompson put his million-dollar Crestwood home up for sale, along with properties in Columbia Heights and Poplar Point. A realtor who handled the sale of one of Thompson’s properties noted that he was looking for a cash transaction. Last September, Thompson put a downtown office building he owns on the market, looking for a “sale as fast as possible,” the realtor told Washington City Paper at the time.

In a 2011 commencement address for law students at Georgetown, Sullivan urged them to be on the lookout for injustice—not just for the poor, but for the wealthy, too. (LL wonders how much that particular bit of encouragement was needed.)

“When all is said and done, this whole system is only about one man’s freedom,” Sullivan told them. When Sullivan’s involved, though, there’s much more at stake than that.

Got a tip for LL? Send suggestions to lips@washingtoncitypaper.com. Or call (202) 650-6925.

Photo by PBS