Spinning Letterman's Scandal

Pit bull defense attorney Gerald Shargel has represented John Gotti and Marc Dreier, and now David Letterman’s accused blackmailer. He talks to Lloyd Grove about why Dave’s not so innocent.

10.14.09 5:25 PM ET

David Letterman has his own television show, millions of fans, a fat bank account, the backing of CBS brass, and the protection of the Manhattan District Attorney’s Office. But Letterman’s accused blackmailer, suspended CBS News producer Robert Joel “Joe” Halderman, has Gerald Shargel.

By most accounts, Shargel is one of the nation’s best criminal-defense attorneys, having won not-guilty verdicts, or surprisingly lenient sentences, for a rogue’s gallery of scoundrels ranging from Mafia boss John Gotti to larcenous lawyer Marc Dreier over a four-decade career.

He’s also a maestro of media management—a potential advantage in a case that is being tried, for the moment anyway, in the Court of Shrieking Headlines. Thus the focus of his exclusive interview with The Daily Beast: Press Handling in Criminal Proceedings, Theory and Practice.

“Even though what Jerry tells you may indeed be advantageous to his client, it’s 99.9 percent of the time not bullshit.”

“Since Letterman is such a cultural icon and such a high-profile figure, maybe in this case it does matter,” Shargel, an adjunct professor at Brooklyn Law School, says when I ask if the tsunami of tabloid ink could influence the ultimate outcome.

The 51-year-old Halderman, a senior producer for the CBS magazine show 48 Hours Mystery, was indicted Oct. 2 on attempted grand larceny after allegedly demanding $2 million from Letterman while threatening to go public with the late-night star’s peccadilloes in the workplace—or at least that’s the version Letterman offered in a remarkable televised confessional the night of Halderman’s arrest.

“And I think for Letterman to get up there and say ‘I’m the innocent victim and I had some consensual sex’—and he actually said some interesting things: He used the word ‘creepy’—well, the last time I tried it, consensual sex wasn’t creepy,” Shargel adds with a smirk.

Trim and boyish, with a salt-and-pepper beard, he looks a decade younger than his 64 years as he holds forth in his den on the Upper East Side, dressed in Columbus Day casual with nerdy ankle-high aqua socks. He’s surrounded by photos of his six grandchildren, plus framed front pages of the Daily News, including his favorite headline: "MY LAWYERS ARE RATS"—one of the late Dapper Don’s angry outbursts caught on an FBI surveillance tape.

“Let me make this clear,” Shargel tells me before pausing to field a phone call from a producer at Good Morning America. “I don’t wish David Letterman any ill. I’m not sitting here waiting for his ratings to drop. I could care less. I don’t spend one moment thinking about the future of David Letterman. That’s not my business.”

In the two weeks since the cops handcuffed and hauled away his client on the sidewalk outside CBS News’ West 57th Street headquarters, Shargel’s business has been to foment public skepticism about the prosecutor’s claims, raise questions about Letterman’s personal conduct, suggest that Joe Halderman has his own story to tell, and otherwise work his contacts in the media to, as Shargel puts it, “level the playing field.” And, oh yes, he's also preparing trial motions to submit by the next court date, Nov. 10.

Shargel explains: “You’re doing whatever you can do to try and level the playing field—at least let the other side know that you’re not going to just lay down. And I hate platitudes like, ‘I can’t wait to go to court,’ that lawyers often give to the press. “We’re not going to try our case in the press.’? I’ve used that once or twice in connection with this case, especially with aggressive TV reporters who shall remain nameless but whose initials are Ann Curry.” Four days after Halderman’s arrest, Shargel seemingly squirmed on camera when the Today show’s Curry pressed him relentlessly to answer the prosecutor’s detailed charges. “All I’m asking you is to be patient—which you are seemingly not,” he told Curry, who kept right on pressing him. For Shargel, who seems instinctively to know what journalists want and how to give it to them, the Curry encounter was a rare instance of mixed signals.

“I’ve never had a publicist. There’s not a drop of ink that was ever spilled as a result of a publicist,” he confides. “I’ve never called a reporter and said ‘Could you insert this?’—whether it be Page Six or a substantive piece. However, I like journalists. If I had not been a criminal lawyer, I would have been a reporter or journalist of some type. From Day One, I became very friendly with the reporters who were covering the courthouse at 100 Center Street.”

Shargel regularly dines out with journalists and authors, CBS 60 Minutes star Steve Kroft and the late Peter Maas among them, and he likes to invite reporters to the periodic jazz concerts he and his wife Terry host in their 2,400-square-foot apartment on East 72nd Street. “Jimmy Breslin was here,” he says proudly. “Joyce Wadler was here.” He describes several journalists, including The New York Times’ Alan Feuer, as “close personal friends.”

Feuer, who got to know Shargel a decade ago covering the murder and racketeering trial of Bonanno family crime boss Anthony Spero, says that the lawyer enjoys a reservoir of goodwill among members of the Fourth Estate. “What Jerry brings to the table is a level of integrity and trust that you, as a reporter, understand—that even though what he tells you may indeed be advantageous to his client, it’s 99.9 percent of the time not bullshit,” Feuer says. “Many if not most lawyers are afraid to engage the press for obvious reasons. Jerry is not. The press is notoriously single-minded in its pursuit of its interests, and clearly uncontrollable. But Jerry is comfortable and competent engaging the press.” Not that skillful press management trumps the facts and the law. Despite Shargel’s best efforts, Spero was convicted.

Kroft, who met Shargel while working on a 60 Minutes piece on the homicidal Hell’s Kitchen crime syndicate known as The Westies, came away impressed by his lawyering skills. “I don't know the facts of the case," Kroft says, "but the difference between Jerry Shargel and a public defender could be the difference between Halderman doing six months and doing 10 years.”

Columbia University Law School Professor Daniel Richman offers a cautionary note. “There are a great many lawyers, particularly on the white-collar side, who believe that shutting up is the best strategy. The case, if it ever comes to trial, will be tried in front of a select jury and a judge, not the public and the press. And those lawyers manage to even up the playing field just fine.”

Shargel argues otherwise. “Why do I talk to reporters as much as I do?” he asks. “I think it’s important for a case. I think the worst thing that a lawyer could say is ‘no comment.’” Shargel recalls that last December, he did come close to terse non-responsiveness when he was retained by the guilty-as-sin attorney-turned-con man, Marc Dreier. He told the media mob: “’The facts of this case are beyond the reach of a sound bite.’ And that was my sound bite. That’s as close to a ‘no comment’ as you’re ever going to hear from me.”

Which is more than can be said of Team Letterman and Manhattan DA Robert Morgenthau; they are close-mouthed on the subject of Shargel. (Dreier, meanwhile, could have been slapped with a 145-year sentence, and Shargel counts it as a victory that his client got 20 years.)

Shargel didn’t take on Letterman’s alleged blackmailer as a client until he received a phone call from a mutual acquaintance the morning after Halderman’s arrest and Letterman’s sensational account to viewers. The producer was one journalist Shargel didn’t know; he first met Halderman that Friday afternoon in a holding pen at the courthouse—after Morgenthau had already issued a press release and staged a full-dress news conference, implying among other things that Halderman had made a veiled threat on Letterman’s young son and declaring: “The message of this indictment should be clear. New York City will not tolerate the coercion or extortion of anyone, be the victim rich or poor, famous or anonymous.”

Shargel, who says he first heard about the DA’s claims hours later from reporter-friends, felt he had to respond in kind. “As Billy Joel said, I didn’t start the fire,” he tells me. “Morgenthau’s press conference and his actual press statement were a little over the top. ‘This indictment should send a message?’ ‘We won’t tolerate conduct’? What? I mean, indictments don’t send a message! Indictments are accusatory instruments that have no evidentiary weight at all. So I felt obligated to respond, and I had an opening. Certainly I had every media outlet in creation on the phone with me. I had to get up there and say something.”

In a series of media print interviews over the next week, Shargel gave a bravura performance. He stoutly maintained his client’s innocence, boasted of Halderman’s sterling professional reputation and even his Emmy awards, hinted at mitigating factors and complications yet to be revealed, darkly suggested that there was much more about Letterman’s private behavior than the talk-show host would like the public to know, and expressed his eagerness to cross-examine the star. Coincidentally or not, seamy stories began appearing in the New York tabloids about Letterman’s workplace “love nest” and his sexual relationship with a former personal assistant who also happened to be Halderman’s live-in girlfriend.

Coincidentally or not, the damaging stories perfectly fit Shargel’s media strategy of shifting the focus from Halderman to Letterman. Did the lawyer leak them? “I’d like to take credit for all that, and I’m not saying I’ve never done it, but many of the things you’re talking about did not come from me and did not come from my client,” he says. “Ordinarily that’s not my style. When I have something to say, I say it for attribution ordinarily.”

Such as: “I think there is more—I know there is more—to the story than what Letterman has said. If the case goes to trial one day, it may be that David Letterman is not the same David Letterman that everyone knows. Plain and simple. It’s like the woman who finds out her husband is cheating on her—it’s the famous words of dialogue in plays and movies—‘I never knew you. I didn’t know who you are.’”

Lloyd Grove is editor at large for The Daily Beast. He is also a frequent contributor to New York magazine and was a contributing editor for Condé Nast Portfolio. He wrote a gossip column for the New York Daily News from 2003 to 2006. Prior to that, he wrote the Reliable Source column for the Washington Post, where he spent 23 years covering politics, the media, and other subjects.