And the very elements that are likely to make his new book, "The Last Mouthpiece," must reading for mobsters, mob watchers and lovers of Philadelphia lore.
The 350-page book, which Camino Books expects to release in May, reprises Simone's long and colorful legal career, which began in 1958 after he passed the Pennsylvania bar and ended in disbarment in 1994 and bankruptcy three years later.
Today, he owes the IRS millions.
Simone rubbed elbows with the best - and worst - of the city's most colorful and controversial characters and represented quite a few of them.
While he's not one to rat anyone out - even his clients who became government informants and testified against him - the inside story on his high-profile cases are bound to make "The Last Mouthpiece" a page-turner.
Simone's clients ranged from Celebrity Room hostess Lillian Reis in the 1960s, the so-called mastermind of the infamous "Pottsville Heist," to mob boss Nicodemo "Little Nicky" Scarfo in the 1980s during the bloodiest Mafia war in Philadelphia history.
Still, he adds, "The most important of all my clients was Bobby Simone."
As one of the city's top defense attorneys, the 67-year-old Temple law grad earned, gambled or gave away an income that often topped $350,000 a year.
"I was kind of liberal with a buck," he admitted.
Today, he lives on Social Security checks and consulting fees as a free-lance paralegal.
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SIMONE'S DEADLIEST client was Scarfo, who in the 1980s was in the cross hairs of nine separate government investigations.
Despite the mob boss's reputation for ruthlessness, Simone said Scarfo never wavered in his trust of Simone's legal judgment.
"He treated me with respect and appreciated my ability to help him," Simone said.
As the 1980s mob war raged, Simone recounts in his book the times he was almost killed, was threatened to be killed and when the government tried to bring him down.
He felt safest when he was standing before a judge.
