Robert Guarante 1968 Booking Photo

Robert Gentile's connections with Robert Guarante, a bank robber seen above with a shirt over his head after an arrest in Natick, Mass., in 1968, intrigued federal authorities investigating the theft of half a billion dollars in art from Boston's Isabella Stewart Gardner Museum in March 1990. (William Rye / The Boston Globe)

They bound the museum security guards and battered 13 masterworks from the museum walls before driving away in a red car fewer than 90 minutes later.

Among the missing art: a Vermeer, a Manet and five drawings by Degas. Two of the paintings — "Storm on the Sea of Galilee," Rembrandt's only known seascape, and Vermeer's "The Concert" — could be worth substantially more than $100 million, if anyone could find away to unload some of the world's hottest art.

Cooking For The Boys

In Hartford, Gentile seemed to inhabit a different world. He is short and round, with a high forehead. His hair is white and he leans heavily on a cane when he walks. He has penetrating eyes and is a pleasant conversationalist when he chooses.

Over the last eight years, he could be found most days at Clean Country Cars, a garage and used car lot on Franklin Avenue in the Hartford's South End. He put a stove and a refrigerator in a service bay and, as he wrote in a court filing, "cooked lunch for the boys."

"I like to cook," Gentile once said. "Macaronis. Chicken."

The list of attendees at his luncheons in bay No. 1, according to someone familiar with the events, could read like a federal indictment. Among others: Hartford tough guy and mob soldier Anthony Volpe and John "Fast Jack" Farrell, the Patriarca family's card and dice man.

Gentile's arrest record begins during the Eisenhower administration, although most of his involvement with the police occurred in the 1960s. Convictions include aggravated assault, receipt of stolen goods, illegal gun possession, larceny and gambling. He beat a counterfeiting case.

During three searches of his suburban ranch in Manchester last year, FBI agents found explosives, a bullet-proof vest, Tasers, police scanners, a police scanner code book, blackjacks, switch-blade knives, two dozen blank social security cards, a South Carolina drivers license issued under the alias Robert Gino, five silencers, hundreds of rounds of ammunition, a California police badge, three sets of handcuffs with the serial numbers ground off, police hats and what a federal magistrate characterized as an "arsenal" of firearms.

There was a surveillance camera trained on the approach to his home. Hanging from a hook inside the front door was a loaded, 12-gauge Mossberg shotgun with a pistol grip, a federal prosecutor said.

Gentile has giving varying explanations for the presence in his home of the weaponry and related paraphernalia. He said some of it had been there so long he forgot about it. Other material probably was dropped off by a friend who is a "dump picker." Gentile's lawyer said he is a hoarder.

He is handicapped by back pain, probably the result, according to multiple sources, of a blow his father delivered with a metal bar when he was 12 years old. He left school two years later to work for his father's masonry business and became the youngest bricklayer and cement mason to join the International Union of Brick Layers and Allied Craft Workers.

He took a stab at the restaurant business in the 1970s, but closed his place, the Italian Villa in Meriden, after two years.

Gentile and his brothers had a reputation as top concrete finishers, according to friends. When union construction slowed in the 1970s, he went to work for a builder of swimming pools in greater Hartford.

Meeting Guarente

Gentile moved from swimming pools to used cars, according to friends and material filed in court. He met Guarente at one of the automobile auctions where dealers buy inventory, said associates of Gentile and a person familiar with the investigation.

A source who claims to have met repeatedly with Guarente beginning in the 1990s said that Guarente was a bank robber whose last arrest and conviction, in the 1990s, was for cocaine trafficking.

"Guarente was Gentile's connection with Boston," said the source. "Until then, Gentile was his own man. He did his own thing, his own way. Guarente was a stone cold criminal and robber. He told me he robbed 30 banks and, toward the end, he was selling huge amounts of drugs."

Said a law enforcement source: "Guarente was the hub of so many people. He is an interesting guy because he is not well known. But he knows everybody."

One of the places Guarente visited, according to a variety of sources, including an FBI report, was TRC Auto Electric, a repair business in Dorchester, Mass., a hangout of reputed Boston mob associate Carmello Merlino.