The Life and Career of Michael 'Mickey' sherman considered as a Courtrooom Jester.

Probably one of the coolest and most laid-back lawyers ever, Michael ''Mickey'' Sherman has been an attorney for more than 30 years and has yet to lose his sense of humor about his career.

Working his way up from public defender to prosecutor to criminal defense attorney, with a few stints in the entertainment industry along the way, Sherman has experienced many shades of the legal world that have contributed to his one-of-a-kind legal perspective and comical outlook, making him one of the nation's most colorful and memorable lawyers to date.

Sherman's legal journey did not have a brilliant and inspiring birthplace; in fact, it is practically a coincidence that he became a lawyer.

"Most really great lawyers go into law because they want to do good things, free people, and achieve justice. Me, I went to law school because all the guys in my fraternity signed up for the law board, and I thought I should be with them," he said. "If I was rich, I'd be a snowboarding instructor the rest of my life."

Soon after he meandered into law, though, Sherman realized that he had the knack to be an attorney.

"It suits me because I'm a wisecracking person, and I have decent communication skills," he said. "I'm not really intelligent; that's for sure. I like to say I graduated in the top 85% of my class. I've never made an honor roll at any time in my life."

After he finished law school at the University of Connecticut in 1971, Sherman worked at the local courthouse for approximately four months before he had proven himself to the judges.

"I sucked up to the judges enough that they gave me a job as a public defender when that opened up," he jokingly said. "Meanwhile, I sucked up to the judges again for that year, so a prosecutor job opened up, and I became a prosecutor." Sherman was a public defender for only a year before he was promoted to a prosecutor position.

Sherman remained in the prosecutor position at the Stamford Superior Court—a job that he called "the easiest job in the world"—for four years.

"You play God from nine to five and then go home, and there's nothing to do but watch TV—virtually no responsibility. It's just so not a difficult job," he said.

Looking back on this point in his career as a current criminal defense attorney, he has been able to distinguish the real differences between working as a prosecutor and working as a defense attorney.

"If you lose, somebody goes free, but they'll probably get arrested again, whereas when you're in defense, and if you lose, some poor man or woman might go to jail who might not deserve that punishment," he said.

After spending four years as a prosecutor, Sherman wanted to pick up the pace of his career.

"At this time, I'm married, I've got two kids, and I'm living in a condo the size of a refrigerator box. The only way I was going to make any real money was going into private practice and making a ton of money or going on game shows."

Shockingly enough, Sherman chose the latter option. Appearing on shows like Jackpot!, The Joker's Wild, and Pyramid, Sherman was able to supplement his income with approximately $25,000 in cash and additional gifts.

"I looked like a professional schmuck," he said of his appearances. "It was fun to shake up the real smart people who were there from Berkeley who had never been on TV or in front of a crowd. I said things like 'Boy, there's only, like, 200 in this audience, but gosh, there's going to be millions watching this.'"

<< Although he had walked away a winner many times in his game show career, Sherman still had not made enough to buy a new house, so he returned to life as a lawyer. He became a partner at Sherman, Richichi & Hickey in 1977 and has been in criminal defense ever since.

In 1988, Sherman helped found the Connecticut Criminal Defense Lawyers Association (CCDLA) in Connecticut, a not-for-profit organization that consists of approximately 300 criminal defense attorneys.

"Criminal defense lawyers, we're generally not allowed where everybody else is," he said. "We're like two rungs, on the social scale of lawyers, below those people who ask you for a dollar on the streets of New York. You know, we do God's work, but we're not really appreciated by the rest of the bar. They look at us like we're Pigpen from the Charlie Brown cartoon."

Sherman is an officer as well as a board member of the organization. He frequently gives various speeches on criminal law around the country for the organization. "I'm not an academic, so to me it's basically doing stand-up in front of a couple hundred lawyers," he said of his speeches.

Unlike some attorneys who shun the media, Sherman is one lawyer who has learned the value of acknowledging and embracing the media but not necessarily making friends with them.

"They're not your friend, but you shouldn't make them your enemy. You should recognize that they're going to be your best friend because they need something from you; they want that sound byte, or they want you to introduce them to your client or your client's wife. They all want something, and you just have to have your eyes open," he said.

"There are ways to let the media know what you think should be highlighted in their coverage. If it's an interesting fact and if it's a legitimate thing, they'll put it out there, or you'll at least give them the road map as to how they might want to cover your case, which will be to your advantage."

<< Speaking of relationships with the media, Sherman took this so far that he married Fox News legal analyst Lis Wiehl on June 23, 2006. Sherman regularly commentates on MSNBC, CNBC, Court TV, Fox News, CNN, and other news channels. He is also employed by CBS News as its legal analyst and regularly appears on the CBS Early Show and the CBS Evening News.

Sherman met his wife during the Clinton impeachment trial, as the two debated the subject on Fox News.

"Our egos are so incredibly large that nobody else can stand us; we had to marry each other," he jokingly commented. But all joking aside, Sherman does believe that handling the hectic and crazy schedules of law and television is tough, so marrying someone who shares the lifestyle definitely helps.

"Sometimes you have to say 'By the way, I'm not coming home tonight. I'm doing Geraldo' or 'I can't do this because I'm doing a radio show.' When you're both in the business, you kind of understand that."

In addition to his television appearances, he has even dipped his toes in film, playing the role of the "Talking Head Lawyer" in the 2006 movie Man of the Year, which stars Robin Williams and Christopher Walken.

Sherman is notorious for having defended many high-profile cases in past years, including the Michael Skakel case, which is currently being evaluated for a retrial. Skakel, Senator Robert F. Kennedy's nephew, was charged with the 1975 murder of Martha Moxley and found guilty in 2002. Sherman represented Skakel in 2002 and claims the prosecution only handed over the composite sketch of Kenneth Littleton, another possible suspect, after the 2002 verdict was given.

On April 19, 2007, Sherman testified for the retrial motion, saying that a sketch of another man seen on the night of the 15-year-old's murder would have helped his case.

"It would have enhanced our case," he said, according to Court TV. "We had an excellent alibi defense. It was the absolute bulwark of our case...Michael Skakel is innocent. He is not guilty. He was not there."

"You have to understand that you don't have all the answers. There's no such thing as a slam-dunk case, no matter what side you're on," he said of his challenges and lessons learned. "Marcia Clark learned that the very hard way with respect to O.J., they learned it in the Robert Blake case, and I certainly learned that in the Skakel case. You learn to be humble and never count your chickens before they have hatched, and you've got to cross your Ts twice."

<<Through the years, many critics have come to question and debate some of Sherman's unique, envelope-pushing courtroom tactics. In fact, in 1986, during a rape trial that Sherman was covering, The New York Times questioned his legal motives when he hired a juror from the deadlocked rape trial to sit through the retrial of the defendant as his consultant. Once the second trial came to an end, the Connecticut Legislature passed a statute that made this move a misdemeanor.

Although Sherman typically incorporates his sarcastic and witty sense of humor into his courtroom discourse, he knows when to get down to business. Referring to his courtroom style, he said, "[It's] not histrionic. I don't put on a big show. [It's] basically very common-sense oriented. I try not to give a lot of B.S. to a jury or a judge. I approach things as humbly as possible, without losing my credibility. I joke around a lot. It's usually self-deprecating, but sometimes I'll make fun of somebody if they deserve it."

He even suggests that all lawyers and law students maintain the same outlook. "Keep a sense of humor about you," he said. "Don't get put off by losing cases; just do the best you can and try not to take yourself too seriously."

Sherman has found that combining a charismatic personality with book smarts can benefit a lawyer tremendously, depending on what type of law he or she practices.

"If you're a securities lawyer, then you can have the personality of an endodontist. But if you're a trial lawyer, civil or criminal, you have to be a good communicator—simple as that," he said. "You've got to be able to connect with 12 people who were unfortunate enough not to get out of jury duty."

During his years as a public defender, Sherman gained some human-relations lessons for the legal world from his boss, Ray Cushing.

"He was just a terrific guy. Legal genius? No. I don't think he ever read a law book in his life," he said. "He had a way of communicating with the client. Public defender clients are tough because they have no trust in you whatsoever."


 

Q. What are your hobbies and interests? A. I ride a Harley-Davidson—but I'm not one of those middle-aged, balding Jewish guys who decided to buy a motorcycle at age 50. I've had a motorcycle since I was 16 years old. I'm a fanatical snowboarder. I've been the old guy on the snowboard for, like, 20 years. I play a lot of golf, tennis, and I like to windsurf. I'd like to say that I read, but I have ADD...although I play myself in one of James Patterson's books, The 6th Target. I was also in 4th of July, one of his other books. Q. What CD is in your CD player right now? A. I have an eclectic collection on my iPod, but it would be Michael Bolton. He's my best friend, and he was my wedding singer. Q. What is your favorite TV show? A. Entourage. Q. What was the last magazine you read? A. Macworld. Q. Who is your role model? A. Johnny "Drama" Chase from Entourage.

Sherman will be the first to tell you that he is not a scholarly lawyer, but he has still managed to snag a high-profile law career in other respects, and Cushing 's example seems to have significantly contributed to that.

"Ray taught me how to be genuine with people and to always remember that whether they're noxious, whether they're guilty, whether they're smart, whether they're dumb, they're people. Everyone is entitled to be treated like a gentleman, even if they don't act like that," he said.

"When someone left that courtroom, whether they were shackled, handcuffed, or free, they knew that they got the best representation that they could possibly get by a lawyer who gave a damn. And that is the case—you've got to give a damn or at least appear and communicate like you give a damn. You've got to show some heart."