In recent years, he went to Latin America as a lay missionary, married a local woman and had a child. Then he brought his new family back to his native Quebec and found work as a security guard at Montreal's most prestigious private school.
Once an infamous mobster, Réal Simard, 53, fashioned himself a new, trouble-free life, but police caught up last week with the man who had vowed he would never go back behind bars.
However, the offence for which the onetime self-confessed Mafia hit man got arrested this time was strikingly banal.
Mr. Simard had been on the lam for five years. But that was because his parole had been suspended in 1999 after he was denounced for using a fake identity and taking a part-time job at the Red Cross while he was a welfare recipient.
To people who know him, sending Mr. Simard back to jail sounds particularly unfair because he had tried for years to stay out of trouble.
In 1985, he confessed to five killings and turned informant. He served his sentence and received full parole in 1994.
But as he struggled to build a new life, his past kept coming back to haunt him. He lost jobs when employers learned of his real identity. He complained that he got more hassle from the authorities than from the mobsters he had betrayed.
"It's sad because he's someone who has made efforts and managed to rehabilitate himself and start a new life -- he's paid his debt to society," said Jacques Fortin, the publisher of Mr. Simard's two books.
"I believe he is totally rehabilitated," said journalist Michel Vastel, who co-wrote one of those books.
"This is a huge squandering of a human life."
The arrest was mortifying for Collège Jean-de-Brébeuf, the private school of Montreal's francophone elite where, for nine months, Mr. Simard was a night watchman under the name Charles Bouchard, a moniker he got off a cemetery tombstone.
"We're really sorry for what happened . . . we hope people will understand. It wasn't in bad faith, we got hoodwinked," school spokeswoman Diane de Champlain told reporters yesterday.
She described Mr. Simard as a friendly, helpful employee, a description that matched the recollections of others who had crossed his path, who recalled his intelligence and charm.
Like Shirley MacLaine, whose book Out on a Limb, he credits with turning him into an honest man, Mr. Simard has led many lives.
The eldest of the five children of an abusive father in working-class Montreal, Mr. Simard looked to mobsters as role models and racked up a record for extortion and bank robbery by his mid 20s.
He found a mentor in mob boss Frank Cotroni, who was trying to establish himself as a worthy successor to his older brother Vic (the Egg), the top Mafioso in Montreal in the 1970s.
Mr. Simard considered Mr. Cotroni his uncle, acted as his assistant, drove him and killed for him.
When Mr. Cotroni wanted to extend his business to Ontario, he sent Mr. Simard there to meet Hamilton crime boss John Papalia to work out the expansion.
The last of the five slayings Mr. Simard committed took place during a settling of accounts at Toronto's Seaway Motor Hotel in 1983. One victim, a drug dealer, survived and fingered Mr. Simard.
After his arrest, he saw the light reading Out on a Limb. He later told The Globe and Mail that "the book made me realize I had a soul."
He turned informant and helped the authorities convict Mr. Cotroni of manslaughter and sentence him to eight years.
With Mr. Vastel's help, Mr. Simard produced a biography, titled The Nephew, an allusion to his relationship with Mr. Cotroni. There followed a documentary, which led a TV reviewer to note that Mr. Simard "has the charm of a gigolo and looks like a cross between heartthrob actor Armand Assante and popster Gino Vannelli."
Mr. Simard got day parole in 1990 and full parole in 1994.
In 1993, using the name Michel Roselli, he was an aide to Parti Québécois MNA Richard Holden. He then helped the campaign of Bloc Québécois candidate Kim Beaudoin.
However, he lost those political jobs when police tipped the PQ about his past. He struggled financially and got in trouble collecting welfare while working three days a week.
He offered to repay the $3,400 he owed welfare authorities but by then his parole had been suspended.
A friend recalled that "he said 'you'll never get me again' and he disappeared."
Until he was caught last Friday.