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One of the epicenters of local political news this year has been the E. Barrett Prettyman Federal Court House, a squat shrine to justice a short drive down Pennsylvania Avenue from the Wilson Building. It was at Prettyman where former Ward 5 Councilmember Harry Thomas Jr. admitted to stealing city funds and later was sentenced to more than three years in prison. It was where two campaign aides to Mayor Vince Gray pleaded guilty to covering up payments they made to fringe candidate Sulaimon Brown. And it was where former D.C. Council Chairman Kwame “Fully Loaded” Brown choked up as he said goodbye to District politics.

Since there are several signs that the federal investigation into Gray’s campaign is far from over, there’s a good chance that Prettyman could be the site of plenty more local political drama to come. If it does, Bill Hennessy will be there with pencils and pads to record the moment for posterity, or at least for a few seconds on local TV news broadcasts.

Hennessy is one of the last local practitioners of a dying art: the courtroom sketch. And if you’re a boldfaced name in local politics and Hennessy is staring at you from the front row or the jury box, you know you’re in deep trouble.

He got his start 30 years ago, when he was a fine arts graduate student at American University. One of the local TV news stations needed a sub for its courtroom sketch artist and called the art department. Hennessy volunteered to give it a shot. For the next three decades, the sketching work put Hennessy in the front row of history more often than Forrest Gump.

The back of his business card bears witness: “Major cases:” it says, with a list that includes: “Impeachment of Pres. Clinton,” “Moussaoui/20th Hijacker,” “Marv Albert,” and D.C.’s own “Marion Barry.”

Hennessy was there during Barry’s drug trial in 1990. On his website, Hennessy has posted a few sketches from the trial. One shows Barry listening intently as Rasheeda Moore—better known as the, um, bitch who set Barry up—testifies. In the background is Barry’s then-wife, Effi Barry, who sat in the front row throughout the trial.

Another shows a stern-looking Barry leaning back in a chair watching a TV play the grainy FBI footage of himself taking a drag off a crack pipe.

The trick to a good sketch, Hennessy says, is capturing the day’s most dramatic and poignant moments in a single frame. “I consider myself a journalist as much as an artist,” Hennessy says.

(Hennessy sells copies of his Barry art and other sketches for up to $1,500, by the way. He’s also got a book of his work, called All Rise.)

All that time covering Barry left an impression. In one of Barry’s subsequent returns to court (for taxes or drugs, Hennessy can’t remember which), Hennessy says he found himself in a tight anteroom with the former mayor-for-life before a court hearing started. “Hey, I know you,” Barry said.

In a way, Hennessy is like the Norman Rockwell of a dystopian District. The description of his archived sketches include “Clown selling drugs to children” and “Lit ex-girlfriend on fire.” Other standouts from Hennessy’s 30 years in D.C. courts include a sketch of a defendant punching his attorney (complete with glasses flying off the poor schlub’s face) and another defendant sprinting down the escalators at D.C. Superior Court in a failed escape attempt.

“He has a knack for being in the right place at the right time,” says Bill Miller, the spokesman for the U.S. Attorney’s Office, who has known Hennessy since the mid-’90s.

But just how much longer Hennessy, or anyone, will be in the right place is an open question. Hennessy says he hasn’t met a greenhorn sketch artist in more than a decade. When people ask him about getting into the business, he recommends against it, saying it’s just too unpredictable a field.

The last few years have been especially tight, as the market for his work has shrunk along with the budgets of local news organizations. (To make ends meet, Hennessy, a father of seven, works as a realtor and is in the process of making his 22-acre spread in Loudoun County a site for weddings.) The Washington Post used to buy his sketches about three times a week, he says, but they haven’t purchased his work in about three years. His sketches used to appear on local TV news almost every day, he says; now it’s only a few times a month. A typical work week used to be 40 to 60 hours; now it’s about 6 to 8.

Hennessey won’t say how much his work costs—“not as much as you think,” he says. (Though someone familiar with the pricing tells LL they aren’t cheap.)

Besides the economics of the news business, though, there’s also the public’s changing tastes. In a world where everyone has a camera on their phone, people expect pictures of their news, not drawings—antiquated court rules on photos and video be damned. When Harry Thomas Jr. showed up at court, LL saw news cameras stationed at all three of Prettyman’s public exits, as no one wanted to miss out on the shot of Thomas making a mad dash to a waiting car. Judges are starting to bend to the public’s appetite for real reality TV. Maryland and Virginia sometimes allow cameras in their courts; D.C. and all federal courts do not.

Maybe one day they will. Maybe one day courtroom sketch art will be as quaint and irrelevant as the printing press. But for now, Hennessy says he’s got no plans to quit: “As long as there’s a call for it, I’ll go.”

Photo by Darrow Montgomery

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