The History of the Mafia in Connecticut


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Wide Open Gambling
In 1953, New Haven elected a new Democratic mayor, Richard C. Lee. Ralph Mele’s old friend Arthur Barbieri was Democratic Town Committee chairman. Barbieri had worked at Golden Crest Ice Cream, which also had supposedly employed Mele. Investigators concluded that the business was a front for Mele’s illegal gambling operation.

Now, the Mob had an ally in New Haven city government. An informant told the FBI that Barbieri gave the word for “wide open gambling” in the city after Lee took office.

Lee had been elected to transform New Haven. Under his leadership, the city would garner more federal urban renewal money per capita than any community in the nation. Lee would use that money to raze entire neighborhoods and transform downtown.

While he didn’t intend to, Lee made the mob rich. The construction work was a gold mine for Annunziato and the operating engineers. Adding to the bonanza was the building of Interstate-95, the first leg of the nation’s interstate highway system.

While Annunziato ran the unions, Tropiano took care of the numbers and shook down bookies.

Tropiano kept a low profile, but Annunziato didn’t. He was arrested on an almost monthly basis for everything from public drunkenness to disorderly conduct to assault. In the mid-1950s, he and his thugs wrecked two restaurants in a suspected scheme to force the owners to sell at rock-bottom prices. One of the brawls, at a Milford restaurant, got so out of control that the police called in the fire department for reinforcements.

But Annunziato had another side that inspired fierce loyalty and even love. He was pathologically generous, routinely handing out $100 bills to friends and acquaintances, and $50 bills to kids. If he knew a person at a restaurant, he’d immediately pay their bill. He would lend people his car or get them jobs at the drop of a hat. Annunziato, it was said by some, had “a heart of gold.”

Annunziato eventually had to serve a year in prison for one of the restaurant incidents, but instead of going to the state prison in Wethersfield, he was allowed to do his time at the Whalley Avenue jail in New Haven. There, he was able to bring in all his meals, and go out at night. He was even reported to have assaulted the son of the New Haven county sheriff who ran the jail.

But it couldn’t last forever. The stint in jail cost him his job at the union. He would remain a power behind the scenes until forced out for good in the late 1960s.

When the FBI began cracking down on the mob in the late 1950s, both Annunziato and Tropiano were targeted.

In 1960, the federal government won a conviction of Annunziato in the bribing of an I-95 contractor. It was the beginning of a long decline for the rotund mobster, exacerbated by the death of his 15-year-old son, who was accidentally struck and killed by a car.

His drinking worsened and he grew more violent and unpredictable. He returned to prison in the mid-1960s after shooting a man in a New Haven tavern.
While Annunziato made more headlines, Tropiano was suspected in one of the Elm City’s most brutal underworld murders. In 1962, a small-time tough named Thomas “Pinocchio” Rispoli punched Tropiano in a gambling dispute.

Less than two weeks later, Rispoli’s battered, bullet-riddled body was discovered in a shallow grave in the dirt basement of an abandoned Branford home. In spite of an intensive investigation, no arrest was ever made.

Tropiano was later convicted of trying to bribe police officers to protect a gambling operation and then of trying to monopolize the region’s trash-hauling industry.
By the late 1960s, the New Haven underworld was up for grabs, and an Irish bank robber tried to step into the breach.

Edmund Devlin put together a crew of Italian and Irish toughs who became one of the nation’s most successful bank robbery gangs up to that time. The gang stole an estimated $500,000 to $1 million (worth $3-$6 million today), most of which was never recovered.

With Annunziato fresh out of prison in 1968, the two gangs fought for control of New Haven’s rackets. The war pitted young men who had grown up together against each other.
It ended in late 1968 with the murder of Richard Biondi, Annunziato’s trusted hit man, and Annunziato’s return to prison. Annunziato and his son Frank were also later convicted of the attempted murder of a member of Devlin’s gang.

Devlin, meanwhile, made the FBI’s Ten Most Wanted list before being caught and sent to federal prison, where he died of a heart attack in 1977. He was just 46.

In the mid-1970s, the FBI inserted an undercover agent into the New Haven underworld. The agent soon learned the extent and depth of the mob’s power in the Elm City. He met numerous local hoodlums, gained entrance to a Mob-run craps game with a $50,000 bankroll and witnessed mobsters, politicians and police hobnobbing like old friends at a social event.

“It has been ascertained that there is an intertwine between criminal elements and law enforcement,” an FBI report said of New Haven. “Further the criminal element all appears to have grown up together or are related to each other in some way by either blood relationship or close companionship over the years.”

One night, the agent accompanied a local gangster (his name is blacked out of FBI documents) to a downtown New Haven hotel, where the agent watched him berate and rough up recently resigned Democratic Town Committee chairman Arthur Barbieri. The mobster was angry about Barbieri’s decision to step down.

The gangster told Barbieri that his people “had spent a lot of money” on Barbieri.  He was “not to make any decisions without [the gangster’s] prior okay,” according to FBI files.
The FBI later removed the agent and no arrests were ever made.

The History of the Mafia in Connecticut

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