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 fade from 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 Manhattan office, proving once and for all that he doesn't understand the concept of retirement.

Surrounded by framed newspaper clippings of his proudest achievements, Brafman recounted the victories that prompted The New Yorker to call him “The Last of the Big-Time Defense Attorneys.” But, he said, he still agonizes over the defeats and still struggles with the public humiliation that accompanies losses in high-profile cases.

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 in an email that night. “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.

“To be candid, I hated everything about today. In truth, I think Martin took his sentence better than I did.”

To explain what the public humiliation is like, Brafman tells the story of an encounter with a well-known oncologist at a charity event. The oncologist said he had always wanted to meet Brafman because they have a lot in common. “What do we have in common?” Brafman asked quizzically.

“Oncologists don't generally deal with humiliation,” he told the doctor. “When you get sick, everyone who loves you becomes closer and supports you. When I deal with someone who is prominent and if their criminal case becomes a matter of public discussion, there's an added dimension of humiliation, which is sometimes the most difficult part of my job.”

In the Shkreli case, Brafman saw his client vilified because the pharmaceutical executive had raised the price of a lifesaving drug for treating HIV to $750 a pill. While the sentence was a disappointment, the verdict wasn't a complete loss.

“In our view, he was acquitted of the most important count, which accused him of intentionally trying to steal other people's money. Given what we had to overcome, I think we did a very good job in that case and I'm very proud of the result,” he said.

Beyond Skhreli, Brafman's client list is familiar to 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, Bonanno crime family boss Vincent Basciano, Cameron Douglas, nightclub owner Peter Gatien, Conservative Party pundit Dinesh D'Souza, former New York State Assemblyman Carl Kruger, former Suffolk County political boss John Powell, Plaxico Burress and Puff Daddy.

Despite the celebrity cache, Brafman insists the work isn't glamorous.

“People ask how I spend my days,” Brafman said. “They think I'm clubbing with Puff Daddy 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.”

Interacting With Prosecutors

Preet Bharara, who was considered by some to be the most powerful prosecutor in America when he was the U.S. attorney for the Southern District of New York, was so impressed with Brafman that he invited him to speak to the staff. Previous guests included four Supreme Court justices, two FBI directors and former New York City Mayor David Dinkins and so Brafman was in good company.

“He was in a position to impart a lot of wisdom that you can't get from a book,” Bharara said in an interview. “Ben Brafman is an old-school guy and I mean that as the highest compliment. We don't have enough of that. When he comes in the room, people don't immediately have their back up. Being disarming and friendly is not weakness. It shows tremendous strength and confidence actually.”

“I think he's one of the most able, if not the most able, criminal defense lawyer in New York and one of the reasons I think Ben is a breed apart is because he fights for his clients fair and square,” Bharara said.

In 1980, when Brafman launched Brafman & Associates, prosecutors and criminal defense lawyers spent more time together because more cases went to trial. Brafman was on trial nonstop for 15 years, sleeping only two hours straight most nights.

“If not for the fact I observe the Sabbath, I think I'd be dead,” said Brafman, an Orthodox Jew who prays, rests and recharges from sundown Friday to sundown Saturday. “I think God knew exactly what he was doing.”

One of the most notorious trials involved the acquittal of Gatien. Gatien was dubbed the “King of Clubs” because he owned prominent nightclubs at which the government was alleging a series of drug deals took place.

U.S. District Judge Frederic Block of the Eastern District of New York, who presided over the trial, wrote about Brafman in his book. “He was brilliant. I never saw a more skilled criminal defense attorney,” he said.

Michael Bachner, Brafman's first associate, called Brafman a brilliant cross-examiner with an innate ability to know when a witness was telling the truth.

“He also has this self-deprecating manner to him despite all the big egos that criminal lawyers have. Even hostile witnesses open up,” said Bachner who now has his own firm.

Asked to identify Brafman's weaknesses, Hafetz & Necheles name attorney Frederick Hafetz said, “None of us are Superman. We all take a step occasionally we wish we didn't take,” but he added, ”I'm a big fan of Ben's.”

Paul Shechtman, a partner at Bracewell, handled an appeal on a case that Brafman tried.

“I thought that Ben's summation was magical,” he said. “I thought the defendant was guilty. The jury thought the defendant was guilty. But there was a brief moment at the end of Ben's summation where I thought the client was innocent.”

When he was a prosecutor, Shechtman had a meeting with Brafman who had come to his office to fight for a client. Shechtman said he knew he was going to deny Brafman's request “but when he was done, I almost did it.”

Brafman said he savors the times when he does get to tell a client he has convinced a prosecutor not to level charges.

“I guess It's like telling someone that they no longer have cancer and they've been cured,” he said. “But I think it's even better because I don't have science on my side and I don't have blood tests and surgery. I don't have cutting-edge drugs that are being developed every day that help me in my work.”

'I Don't Represent Terrorists'

While acknowledging that he has clients who have been charged with murder, Brafman draws the line at terrorists.

He believes that reviled terrorists deserve the best representation but said he is not the right person. It's not that he sits in judgment but that he's been in the business long enough to be selective about the cases he takes.

“You can't pass moral judgment as a criminal defense lawyer,” he said. “Once you start doing that, you can't do this kind of work because most of the people who come to you are not picked out of the yellow pages for the distinction of having to hire a criminal defense lawyer.”

The prevalence of terrorism and the rise of anti-Semitism in Europe account in part for Brafman's reluctance to retire and travel. He no longer feels welcome beyond the United States and Israel.

Brafman, who has been an emcee or keynote speaker at more than 100 charitable events in the last five years, many for Israel and the Jewish community, 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.”

But he finds it easy to follow his faith, nevertheless, because observing the Sabbath as a modern Orthodox Jew in the United States is no sacrifice compared to the horrors his ancestors endured. Brafman's maternal grandparents, aunt, uncle and cousin were murdered at Auschwitz and his father was arrested by the Gestapo on Kristallnacht. “I remember saying at my mother's funeral that today, the day she died, is the only day she is not afraid,” Brafman said.

With no prospect of retirement in sight, Brafman sees his job as a criminal defense lawyer and the ability it gives him to support the causes he believes in as ways to practice his religion. The job and Judaism are ironically closely aligned.

“One of the fundamental teachings of Judaism is giving people the benefit of the doubt,” he said.