During a 40-year career as one of the city's top defense lawyers, his clients included the glamorous and the infamous, from mob bosses to showgirls, from union leaders to porn stars.
"He was the last of the big-city, big-time, hard-hitting criminal lawyers," said Edwin Jacobs Jr., a prominent Atlantic City defense lawyer and longtime friend and associate.
Mr. Simone's career was launched with the high-profile defense of showgirl Lillian Reis, who was charged with masterminding the theft of $478,000 from the home of Pottsville coal baron John Rich in 1959.
His most infamous client was mob boss Nicodemo "Little Nicky" Scarfo, whom he defended in numerous federal and city cases in the 1980s and who became Simone's friend as well as client.
"When I had problems, he was one of the people who stood behind me," Mr. Simone said in a 1988 interview before the start of a Common Pleas Court murder trial in which he successfully defended Scarfo.
"I consider him a loyal friend to have."
Other clients over the years included mob leader Angelo Bruno, Roofer Union head John McCullough, drug kingpin George "Cowboy" Martorano, and porn star Linda Lovelace (who hired Mr. Simone to settle a personal appearance contract dispute with two promoters).
Mr. Simone's loyalty and sense of honor were paramount in a career that often had him clashing with federal prosecutors in court and ducking federal investigators on the streets.
He was indicted three times by federal grand juries. Putting the lie to the adage that a defendant should never represent himself, he successfully beat an income tax evasion charge in 1984 and a perjury case in 1986.
His defense in the tax evasion case, in which authorities alleged that he had hidden assets and avoided the payment of nearly $1 million in taxes, was classic Bobby Simone.
After the indictment was announced and he was asked by reporters about the charges, he explained that his money had gone to pay gambling debts.
"Who was I supposed to pay, the IRS or the loan sharks?" he asked with a look that said the answer was self-evident. "The interest is about the same, the health aspect is a little different."
Mr. Simone, however, lost his last battle with the federal government when he was convicted of racketeering and extortion charges in a 1992 case tied to the Scarfo mob. Authorities alleged he had become the "unofficial consigliere" of the crime family, an allegation he vehemently denied.
He was sentenced to four years in prison and stripped of his license to practice law.
Mr. Simone wrote extensively about the case and about what he considered the government's abuse of the legal system by making deals with criminal informants in his book The Last Mouthpiece.
A memoir that highlighted most of his major cases, the book was published in 2001 after he had completed his sentence on the racketeering charges.
He eventually had his license to practice law restored and was again working as a defense lawyer when he was sidelined with the illness that took his life.
"He was an outstanding lawyer who went toe to toe with the government and never gave an inch," said Norris Gelman, a defense lawyer who worked on cases with Mr. Simone.
"He was the last of a breed. ... He knew tactics, he knew strategy, he knew how to cross-examine."
Even prosecutors, who investigated and built cases around what one referred to as Mr. Simone's "dark side," said he was a master in the courtroom.
"He was one of the best trial lawyers I ever went up against," said Louis Pichini, a former federal prosecutor and Organized Crime Strike Force attorney who won numerous battles with Simone, including the major racketeering case that sent Scarfo and his top associates to prison in 1988.
"When he was cross-examining a witness, he had an intuitive sense of what to ask and, as important, when to stop asking," Pichini. "It was like a surgical strike. Get in and get out."
Robert Madden, the former federal prosecutor who later became a defense lawyer, said Mr. Simone "was a legend ... a great lawyer."
More important, said Madden, "he was a man of his word. If he told you something, you could bank on it. That's the way it was going to be."
The son of a first-generation Italian American father and a mother born in South Philadelphia, Mr. Simone grew up in the Logan section of the city, attended Olney High School, and then went on to Temple University and Temple University Law School.
In his book, he said that from the time he was a boy he dreamed of becoming a lawyer.
"Whenever I saw a courtroom scene in the movies and later on television, I always imagined myself to be the lawyer representing the underdog," he wrote. "...There was no other profession or business that interested me."
He began practicing law in 1959, and after work would often stop into the Celebrity Room, a Center City nightspot run by Lillian Reis.
They became friends and she hired him to represent her in several classic battles with the city and then Police Vice Squad Captain Clarence Ferguson, who was always trying to shut down Reis' club on morals charges.
When Reis was implicated in the Pottsville heist, she turned to Mr. Simone, who defended her through two trials. The first ended in a hung jury. The second ended with a conviction that was overturned on appeal. The charges against her were then dropped.
In the 1988 interview, Mr. Simone acknowledged that he often became friends of his clients' and also with individuals whose reputations were less than pristine. These would include many prominent mob figures, including Reis' boyfriend and co-defendant in the Pottsville case, Ralph "Junior" Staino.
"I can't help it," Mr. Simone said. "That's the way I am. ... I've had dinner with them. I'm not afraid to be seen with them."
Then he smiled and offered one of those crooked glances that were so much a part of his courtroom style.
"Most have records as clean ... as the judges in City Hall."
Mr. Simone acknowledged in his book that his lifestyle was often at odds with his profession. He liked to drink and to gamble and to associate with people who shared those interests.
But he also contended that he was the victim of federal authorities who had targeted him because he was such a strong advocate for those he considered "the underdog."
That, in fact, was one of the themes he returned to again and again in his book. It also was the basis for a one-hour documentary about him that was broadcast on the History Channel in 2003 titled Mouthpiece: Voice for the Accused.
Prosecutors and investigators said their cases showed that Mr. Simone had "crossed the line" in his associations with mobsters such as Scarfo and that he was offering them more than defense counsel. He had become, they alleged, an advisory in a criminal enterprise.
Simone went to jail and returned to Philadelphia denying that allegation while at the same time demonstrating the loyalty that was so much a part of his admittedly flawed character.
"I have paid a hefty price for my long-ago decision to take on the causes of the most undesirable and unpopular among us," Mr. Simone wrote in the prologue to his book. "...And while some of my former clients currently sit in jail or have met ends as untimely as they were grisly, I can tell you that many of them were, and still are, my close friends."
Funeral arrangements are being made through the Baldi Funeral Home, 1331 S. Broad St.
Contact staff writer George Anastasia at 856-779-3846 or email@example.com.