Bob Bennett stands in his office, with his fish mounted on the wall. (Bill O'Leary/Washington Post)

Look at my fish,” Bob Bennett grumbles, waving his meaty arm toward the back of the room. “Stand up and look under its mouth. It says it all.”

A speckled brown trout, wrestled from the Missouri River in the mid-1980s, hangs mounted in the D.C. superlawyer’s office. Below its agape mouth, a lament: “If I kept my mouth shut, I wouldn’t be here.”

Bennett’s clients have included presidents, secretaries of defense and star journalists. Framed photographs of their beaming faces make up a cluttered trophy shelf of their own. And now, he’s tasked with keeping D.C. Mayor Vincent C. Gray (D) from having to see the inside of a jail cell, or perhaps even the inside of a courtroom. Step One may be getting him to learn from the fish.

“One of the more difficult things in representing high-profile clients is that they’ve gotten where they are because they are great communicators who convince people of whatever they want to convince them of,” Bennett says. “And very often, I want to tell these folks that they are now in a place where that doesn’t necessarily work.”

This week, federal prosecutors said in court that Gray knew about an illegal fundraising operation that helped him win the 2010 election. Using testimony from businessman Jeffrey E. Thompson — who may have conspired to pump more than $660,000 in illegal donations to the campaign — prosecutors pointed to an alleged plan in which the mayor would use the code name “Uncle Earl” when communicating with Thompson.

After Thompson’s testimony, Gray went on a barnstorming media tour, chatting with such news organizations as The Washington Post, NPR and CNN to call the accusations lies and to say he would not be resigning. This is not ideal for Bennett, who might rather his clients avoid speaking altogether, but he’s diplomatic about it.

“I understand elected officials have a constituency and they feel like they have to answer some questions,” he says. “I have to be a little bit flexible but still manage the best you can what they say and what they don’t say.”

In the real world, not all fixers look like Olivia Pope on the TV show “Scandal.” This one is a squat man in his mid-70s with white hair and shoulders that hunch up to his ears when he sits at his desk. His job description, too, is essentially a frumpier version of the fictional one: work the city he knows best to try to keep his clients from having to go to court but spend countless hours preparing for the day he won’t be able to avoid it.

“Preparation — that’s the Bob Bennett approach,” says Billy Martin, a D.C. lawyer who has represented Monica Lewinsky’s mother, basketball star Allen Iverson, and NFL quarterback Michael Vick. “If you want to know what Bob is going to do, it’s discredit any witness who tells a story different than the one his client wants to tell.”

That starts with the testimony from Thompson.

“The agreed deal — you’d think he pled guilty to possessing a few marijuana cigarettes,” Bennett says. “Such a generous deal, and you have to question his motivations.” Thompson faced up to five years in prison; he was able to lop that to a six-month maximum sentence by cooperating and talking with prosecutors.

It’s a tricky situation for the mayor, having to balance what is best for him legally with what is best for him politically. Talking can get you in legal trouble; not talking allows a story of possible corruption to go unanswered just weeks away from a contentious primary. But he does have one thing going for him: Bennett is “viewed as one of the top trial lawyers, and I think the mayor is fortunate to have him as his lead counsel,” says Martin, who has known Bennett since the late 1980s.

Gray’s fortune in this regard has its roots as far back as 2001, when his daughter, Jonice Gray Tucker, in her first week as a lawyer at Skadden Arps, was assigned to work with Bennett on a case. Bennett said he met the mayor at a fundraiser Tucker had thrown for him and that when Gray approached him some three years ago for legal help, he agreed.

It’s not surprising that Bennett would have some kind of connection to Gray; his job is to know everyone in the city. This is what happens after you’ve helped President Bill Clinton navigate the Paula Jones scandal (even if the Supreme Court did rule unanimously against him in that case), after you’ve gotten Judith Miller out of jail for her involvement in the Valerie Plame CIA leak story, and after you’ve worked for both Clark Clifford and Caspar Weinberger, Democratic and Republican secretaries of defense, respectively. He’s also very familiar with former education secretary and conservative pundit Bill Bennett. They’re brothers.

Bennett likes to point out, however, that he was not born into this role. Growing up in Brooklyn (you can hear the nasal accent still today), he always thought he wanted to be a doctor. But as he got older, he said he found himself hanging around courtrooms. “They were free, and they were one of the greatest shows around,” he said. So, after getting a bachelor’s degree at Georgetown, he stuck around to get a law degree there (picking up moving and janitorial jobs to pay his tuition) before heading to Harvard for more legal education.

But he has more than found a home in the nation’s capital, working for politicians on both sides of the aisle, and working big corporate cases such as the Enron scandal. He’s even written a book, “In the Ring: The Trials of a Washington Lawyer.”

“I think it is always a benefit if [lawyers] understand Washington,” he says. “It’s a benefit to know the players and the music of the town.”

And for Bennett, the real beauty in the music are the notes not played. Even when talking about his own downtime, Bennett knows when it’s best to not be available to comment. Take, for example, the monthly poker game Bennett has reportedly been holding for decades. Chief Justice John G. Roberts Jr. is said to attend, and so is Justice Antonin Scalia.

But ask Bennett about the game, and he glances fleetingly at his mounted fish before saying: “I’m going to be off the record. Stop the tape.”


A jury of his peers: There’s no shortage of verdicts on Bob Bennett’s handling of the president’s case.

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