What It's Like to be Ben Brafman: Confessions from NY's Most Famous Criminal Defense Lawyer

The prosecutors these days are younger than Ben Brafman's children, and the criminal defense lawyers who have operated in his orbit for the last four decades are all retired or dead. But don't expect Brafman, 69, to leave the limelight. Why? "It’s kind of too late in my life to start a second career," he said during an interview in his midtown office on Manhattan's East Side, proving once and for all that he doesn't understand the concept of retirement. Surrounded by framed newspaper clippings of some of his proudest moments, Brafman recounted the victories that prompted Jeffrey Toobin of The New Yorker to call him "The Last of the Big-Time Defense Lawyers." But, he said, he still agonizes over the defeats. What was it like to be Brafman on March 9, the day that pharmaceutical executive Martin Shkreli was sentenced to seven years for stock fraud? "It was a very draining day, both emotionally and physically and for several days coming into today, I had virtually no sleep as my mind and heart kept racing with anxiety," he said that night in an email. "When the guidelines are 27 years and the government is insisting on 15 years, a seven-year sentence might look good to some. To me, it was terribly disappointing. I have come to like Martin and believe him to have great potential. The thought of him spending several years in a federal prison honestly breaks my heart. To be candid, I hated everything about today. In truth, I think Martin took his sentence better than I did. I believe I gave Martin everything I had and feel very proud of my effort, yet right now, I feel very sad." Shkreli, dubbed the "most hated man in America" for raising the price of a lifesaving drug used to treat HIV to $750 a pill, is only the latest of Brafman's high-profile clients. The other names are familiar to most members of New York's legal community, but for the uninitiated, they include Harvey Weinstein, Jay Z, 50 Cent, Michael Jackson, Dominique Strauss Kahn, Genovese crime family boss Vincent Gigante, Bonano crime family boss Vincent Basciano, Cameron Douglas, Plaxico Burress and Puff Diddy. Despite the celebrity cache, the job isn't all that glamorous, Brafman insists. "People ask how I spend my days." he said. "They think I’m clubbing with Puff Diddy or throwing passes to Plaxico Burress in my backyard. I’m not. Sometimes I’m on my hands and knees before some very young prosecutors begging to get an ounce of future for some soul whose whole life is on my shoulders.” While Brafman, an observant Jew, doesn't socialize with his clients, he does spend time at dinners and dances on the charity circuit. He has been an emcee or keynote speaker for some 100 events over the last five years and is a major supporter of Jewish organizations. "When I was growing up, it was hard for a Jewish person to get a job in some of the firms on Wall Street," he said. "Today they have Kosher sections and so we’ve come full circle. I’m delighted by it and I’d like to think someone like me had something to do with the increased tolerance." But while there's been progress in Brafman's own world, he is pained by the hatred beyond his sphere of influence. Brafman, whose maternal grandparents, aunt, uncle and cousin were murdered at Auschwitz, bemoans "this world of indiscriminate violence and mass murder that is essentially just out there. It terrifies me that this is the world I’m going to be leaving my children and grandchildren." His aversion to terrorists is so strong that he won't defend anyone accused of such a crime although he does, on occasion, represent murderers. He acknowledges they deserve the best representation possible but said he is unable to provide that.