It’s difficult to imagine Bobby Simone in prison, penning The Last Mouthpiece, his I-was-a-mob-defense-attorney autobiography. Difficult because prior to his incarceration, Simone was the power-dressed Philly-lawyer-about-town often profiled on TV and in the newspapers as the eternally tanned bon vivant who practiced a brilliant form of criminal law. A homegrown F. Lee Bailey, Simone was a hotshot defense attorney strutting his stuff in high-profile cases in Philadelphia and as far afield as Chicago and Miami.

Bobby — no one ever called him Robert — Simone’s legal career was one long, almost uninterrupted winning streak, but his personal life was an entirely different matter. Often in hock to bookies and loan sharks, Simone gambled away vast sums of his hard-earned cash. His gambling addiction, drinking binges and the occasional girlfriend-on-the-side were some of the reasons his first and second marriages went bust. And the same government that Simone had beaten in court for decades finally beat him. Betrayed by friends and former clients, Simone was denounced, convicted for racketeering, humiliated and led off in handcuffs. The one-time high roller was suddenly just another convict, eyeing the distant, blinking lights of Las Vegas from the window of his prison cell in the Nevada desert. In khakis and with a 10 p.m. curfew for head count, Bobby Simone had a lot of time to contemplate his eventful life.

Simone turns out to be a witty and opinionated writer; Mouthpiece tells a lot of good stories, albeit with a few mysterious gaps and loyal silences concerning some of the Mafia bosses he calls friends. The early chapters evoke a time, the early ’60s, when Philadelphia politicians, showbiz folk, gangsters and cops were closely, and sometimes corruptly, interconnected. Simone recalls glam-show girls hobnobbing with tycoons, mobsters and politicos in Philly’s hottest nightspot, the Celebrity Room; gruff, two-fisted cops like Frank Rizzo, who locked up one of Simone’s early clients; courtroom adversaries like the young district attorney Arlen Specter; and no-nonsense judges like Emanuel Beloff, the father of former city councilman Lee Beloff (the same Lee Beloff who went to jail in the 1980s for his role an organized crime extortion case).

Simone’s big break came when famous showgirl and nightclub owner Lillian Reis hired him to defend her against charges that she’d helped orchestrate the burglary of a greedy upstate coal baron. The trial attracted the attention of the national media — The Saturday Evening Post profiled Reis with the headline "They Call Me Tiger Lil." Although Reis was convicted, Simone got the verdict overturned on appeal and the state decided not to retry her. Simone’s reputation was set. It didn’t hurt that Simone went on to represent Reis in a libel suit against The Saturday Evening Post for its story linking Reis to the crime. The jury awarded Reis a million bucks, and suddenly Simone was in demand.

Simone went on to represent a number of high-profile mobsters, some of whom he befriended. In later chapters, Simone is reticent about mob friends like Nicky Scarfo, a practice which makes for sound lawyering but weak storytelling. In places, Simone’s discretion hobbles the narrative. In more than one chapter someone is killed or disappears, and Simone chooses not to relate useful background information — public record stuff — about who-done-it and why.

Simone represented many alleged Mafiosi and often got them acquitted. That is the reason, he argues, that the U.S. Department of Justice targeted him several times for criminal prosecution. Simone is no conspiracy theorist; it will surprise readers who think they know Simone’s "reputation" that several U.S. District Court judges objected to the U.S. Attorney’s vendetta against Simone. One federal judge even went so far as to appear as a character witness on his behalf. Simone is fair-minded about most of his adversaries, naming names of FBI agents and Philadelphia policemen who proved to be straight shooters. This attitude makes it harder to dismiss Simone’s contention that he was sent to prison for no other reason than humiliating Justice Department attorneys by beating them in court. In the last part of his book, Simone raises the fundamental constitutional issue that lawyers who successfully represent the "wrong people" may themselves end up as the targets of retaliation by our own government.

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