Known as "Bobby" to clients and colleagues, Mr. Simone fought his most storied legal battles on behalf of the mob boss Nicodemo "Little Nicky" Scarfo, who became his friend as well as his client.
But his confrontations also included several battles in which he defended himself against criminal charges. He was convicted in 1992 in a mob-related racketeering and extortion case, and ultimately served nearly three years in prison.
He vehemently denied the charges in the case, claiming he was the target of a government vendetta. But he also was quick to admit that his lifestyle - a penchant for gambling, nightlife, and a good glass of liquor - often created problems that his courtroom skills couldn't solve.
During his 40-year career as one of the city's top defense lawyers, his clients included the glamorous and the infamous. Scarfo, mob leader Angelo Bruno, union boss John McCullough, and porn-film star Linda Lovelace all called on Simone for legal assistance.
"When he was on top of his game, there was nobody better," said defense lawyer Donald Manno. "He was a combination of instinct, charm and legal talent."
Mr. Simone's career was launched with the high-profile defense of Lillian Reis, a Philadelphia showgirl 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 Scarfo, whom he defended in numerous federal and city cases in the 1980s.
The two developed a close friendship that resulted, among other things, in Mr. Simone's showing up on FBI surveillance photos taken at Scarfo's home and on his yacht, Usual Suspects, in Fort Lauderdale, Fla., in the early 1980s.
Mr. Simone was unapologetic about his personal association with the mob boss.
"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."
Mr. Simone's career often had him clashing with federal prosecutors in court and ducking federal investigators on the streets.
He was indicted four times by federal grand juries. Putting the lie to the adage that a lawyer should never defend 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 he had hidden assets and avoided the payment of nearly $1 million in taxes, was classic Bobby Simone.
After the indictment was announced and reporters asked him 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 subsequently pleaded guilty to a related income-tax-evasion charge, and 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: The Man Who Dared To Defend the Mob.
A memoir that highlighted most of his major cases, the book was published in 2001 after he had completed his sentence on the racketeering and tax 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."
Many of today's young defense lawyers, Gelman said, are like "tax accountants," well versed in the minutiae of deal making and the point system judges use to level sentences, but often lost in front of a jury.
"Bobby was not a tax accountant," Gelman said.
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 said. "It was like a surgical strike. Get in and get out."
Robert Madden, a former federal prosecutor who later became a defense lawyer, said Mr. Simone "was a legend . . . a great lawyer."
More important, Madden said, "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 went on to Temple University and Temple 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, opening a small office in Center City. After work, he would often stop into the Celebrity Room, a famous Locust Street nightspot run by Reis.
They became friends, and she hired him to represent her in several classic battles with the city and Capt. Clarence Ferguson of the police vice squad, who was always trying to shut Reis' club down 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 with his clients and also with individuals whose reputations were less than pristine. These would include many prominent mob figures, including Reis' boyfriend and codefendant 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 targeted him because he was such a strong advocate for those he considered "the underdog."
"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."
Mr. Simone died after a long battle with chronic obstructive pulmonary disease, according to his brother, Joseph.
In addition to his brother, he is survived by a son, Scott; a daughter, Kimberly Ikehara; and two grandchildren.
A viewing will be held from 7 to 9 p.m. tomorrow and from 9:45 to 10:45 a.m. Saturday at the Baldi Funeral Home, 1331 S. Broad St. A Funeral Mass will be said at 11:30 a.m. Saturday at St. Monica Roman Catholic Church, 17th and Ritner Streets. Burial will be in Holy Sepulchre Cemetery, Cheltenham.
Donations may be made to the American Lung Association, 303 S. 13th St., Philadelphia 19107.
Contact staff writer George Anastasia
at 856-779-3846 or email@example.com.