Gaetano Milano, a sharpshooting young gangster who renounced the mafia and experienced a religious rebirth after gunning down one of New England’s most ruthless mob bosses, died early this week.
He was 74 years old and died of heart failure in a Boston hospital on Monday.
In 1991, Milano was at the center of the country’s most riveting mob trial, which unfolded over a long, hot summer at the federal building in Hartford. He was one of seven members or associates of the then-powerful Patriarca crime family charged with a long list of of racketeering offenses — among them, the assassination of mob underboss William Grasso of New Haven.
Milano would later admit pulling the trigger and weep bitterly for having done so. He renounced the mafia, repented utterly and embraced religion in prison. In 2008, the judge who once considered sending Milano to prison for life was so persuaded of the sincerity of the conversion that he reduced the sentence, leading to Milano’s early release — and continuing questions about the character of the man he confessed to killing.
Grasso was a sputtering, spitting, seething cauldron of rage known as “The Wild Guy.” He acknowledged to an informant once that his big career break was an extortion conviction that put him in federal prison, where he became mob Boss Raymond L.S. Patriarca’s cellmate.
Reputed New England organized crime boss Raymond L.S. Patriarca is show in this 1967 photo.
In the 1960s, long before convictions in Hartford and Boston effectively destroyed the mafia, Patriarca was one of the most powerful men in New England. Hidden FBI microphones captured him charging recording industry executives for airtime on radio stations and listening to complaints from insurance executives about auto thefts.
When Grasso was released from the federal penitentiary in Atlanta in 1973, Patriarca made him his underboss, or second in command. Grasso turned his attention to expanding the family’s territory, pushing the New York mobs out of New Haven, Hartford and Springfield.
Gangsters from Stamford to Springfield who dared to challenge Grasso disappeared or turned up dead. One of them, an old Grasso partner named Ralph “Whitey” Tropian who was affiliated with New York’s Colombo crime family, was cut down by gunfire from a passing car in broad daylight in April 1980. He was said to have been considering a return to business in New Haven.
“Why do we go for years and years in Connecticut without a hit and now … ?” an FBI agent in New Haven mused after Tropiano became the third Connecticut gangster to die or disappear in less than a year.
To cement his control over western Massachusetts, Grasso administered the mob’s secret blood oath and inducted two new Patriarca soldiers from Springfield. Milano was one of them.
What Milano and all the other mobsters who reported to Grasso soon learned was how terrified they were of the new underboss. They hated his greed, yet handed over half of whatever they made from running card and dice games, putting loans on the street at exorbitant rates, from insurance scams or simply from stealing. To do otherwise could be fatal.
Patriarca gangsters in Hartford, Springfield and Boston, fed up with Grasso’s greed and convinced they were on his short list of victims, decided to strike first. Their plot to kill him was outlined in prosecution papers and testimony at the Hartford trial. It was part of a wider attempt by disgruntled Patriarca factions in Hartford and Boston to seize control of the family.
The Hartford crew, over which Milano had asserted himself, got Grasso into a van on the pretext of a meeting in Worcester. Always angry, Grasso was raging about being late. He hoisted himself into the front passenger seat. Milano climbed in behind him and fired a .32 caliber bullet into the back of his neck. The mobsters turned the van around, pulled off the highway and dumped Gasso in a patch of poison ivy along the Connecticut River in Wethersfield.
June 21, 1989 – Pallbearers carry the coffin of William Grasso from St. Michael’s Church in New Haven after his funeral.
Milano was charged and convicted of Grasso’s murder on the testimony of two co-conspirators, father and son Hartford gangsters John “Sonny” Castagna and Jackie Johns. The two took a plea bargain deal from federal prosecutors and joined the federal witness protection program.
Milano’s sentencing in Hartford in November 1991 was high drama. U.S. District Judge Alan Nevas would impose sentence. He considered the months-long mob trial a high point in his career and he was one of the harshest sentencers in the district.
Milano’s family and friends packed Nevas’ courtroom. He he had denied for months having anything to do with Grasso’s murder and everyone, including his wife and parents, expected he would continue to do so. But there was an unexplained delay. And when the U.S. Marshalls led Milano into the courtroom, in shackles, his lawyer, F. Mac Buckley, told Nevas that Milano had something he wanted to say.
“All my life I’ve tried to help people,” Milano said, beginning a rambling monologue racked by sobs. He seemed to be trying to say that he swore allegiance to the Mafia to protect people from evil. “And that was the reason for my association.”
“It was like touching a spider web,” he said, thin and drawn after months in jail. “Once you touched it, you just couldn’t let go.”
He decided to kill Grasso, he said, because he was convinced the underboss had decided to kill him. There had been witnesses over the four month trial the previous spring and summer that supported his claim.
“I never buried nor helped bury or killed anyone for Mr. Grasso in my entire life,” Milano said, referring to the secret mob grave beneath a garage in Hamden where Grasso buried victims. “But I do take responsibility for Mr. Grasso because it was either kill or be killed.”
Nevas, was stunned.
“Are you telling me you killed Mr. Grasso?” he asked.
“Yes, sir,” Milano answered. “I am.”
Milano then broke down in sobs, and only snatches of what he said were comprehensible: “I know I’m losing my wife and my children. … I wholeheartedly renounce my membership in this organization. People like William Grasso — all they do is maim or destroy people, make people disappear.”
When Milano collected himself, Nevas told him the sentencing was one of the most difficult in which he had been involved.
“To sit here and look someone in the eye and say you’re going to go to jail for the rest of your life is a very difficult job,” Nevas said. “But all that changed today because of what you stood here and said.
“I can’t send you back to your wife. I can’t send you back to your children. You did a terrible thing. You killed another human being. No matter how evil a person he was — and he was an evil man — no one has the right to kill another human being under those circumstances.”
Nevas had intended to impose a sentence of life without parole. Instead, he sent Milano, then 40, to prison for 33 years, meaning he had a chance to get out alive.
Milano met Nevas again in court 17 years later in 2008 and there was not doubt then on Nevas’s part about Milano’s sincerity. H reduced the sentence by another seven years, setting in motion Milano’s release. He was then 56.
In prison, among other things, Milano taught himself to counsel other inmates, in particular young men whose offenses were associated with drug and alcohol use. He also became a talented and self taught artist. Some of those with whom he corresponded could count on receiving extraordinary, hand-painted cards at Christmas.
Milano’s new lawyer, Craig Raabe, described his client as a model prisoner who found comfort in faith and counseled younger inmates.
Nevas said he had received letters supporting Milano’s release from prison guards. And he complemented Milano on his artwork.
“So your rehabilitation, Mr. Milano, has been extraordinary and remarkable,” the judge said. “You did commit a terrible crime. The description of the actual crime itself was chilling.”
“It’s been an incredible odyssey,” Milano replied.
After his release, Milano taught art therapy and counselled people with drug and alcohol dependencies in western Massachusetts.
Over many years, Milano became close friends with Ray Lopez, who was one of the most active probation officers at the federal court level until his retirement. Lopez has written a book called “The Painter,” based on Milano’s experience