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With Gentile gone, it may be time for a new approach to the Gardner heist

In 2015, Bobby "The Cook" Gentile was brought into the Hartford federal courthouse in a wheelchair.Cloe Poisson/Associated Press/File

For three days, Bobby ”The Cook” Gentile had denied any involvement or inside knowledge. But near the end of my questions, he asked me to turn off my tape recorder so he could ask me something: What could he expect in return for giving me his first-ever interview for the book I was writing on the Isabella Stewart Gardner Museum art heist?

It was early in 2014, and Gentile had just gotten out of prison. He’d been the target of an intense federal investigation triggered four years before, when the widow of Gentile’s longtime friend, another mob associate, had told investigators that her husband, just before he died, had handed off two or three of the masterpieces to Gentile.


Gentile denied it all and spent much of our time together railing against the FBI and federal prosecutors for trying to force his cooperation. They had set him up to sell prescription drugs to an undercover informant, he said, and while he was serving time for the crime, they had raided his house and a backyard shed in a vain search for the artwork. The widow had lied, he insisted: While he and his late friend were interested in finding the artwork because they wanted the reward money, neither of them knew anything about the theft, or what had happened to the stolen art.

Questions regarding Gentile’s involvement in the case followed him to the grave. After his death at 85 at a Hartford hospital last week, news accounts reported him as the last remaining “person of interest” who the FBI believed might be able to solve what is considered the greatest art theft in world history. But I was reminded of what his lawyer said to me soon after I told him about the curious details of our long 2014 interview.


I sensed Gentile was trying to open a dialogue toward our working together on a tell-all book — he would confirm all the suspicions about his involvement, and make some money in the process.

There was good reason to suspect he knew something big. In addition to the information from his late friend’s widow, the FBI search of his home had found a piece of paper listing the price that each of the 13 stolen items would have fetched on the black market. And hadn’t he told a jailhouse snitch that he’d hidden the paintings in a ditch underneath his backyard shed, but they’d been ruined in a flood a few years before?

Forget it, A. Ryan McGuigan, Gentile’s lawyer, told me. Bobby’s a con man. And while you may get some suspicious details out of him, there’s no big reveal regarding him and the Gardner case. In the end, Gentile ended up in jail because he’d tried to make something out of nothing — he was the biggest victim of his own con.

But his death has left me to wonder: What was it that prevented Gentile from being more cooperative with the investigators? Why would he have taken such a combative attitude toward them, and might there have been some way of getting him to open up?

But like so many mob associates whose names have been linked to the crime, Gentile grew up in a world where the FBI could not be trusted and omertà — refusing to cooperate — was the code to live by.


In Gentile’s case, that skepticism may be justified. At the same time the FBI in Hartford knocked on Gentile’s door asking him to assist them, they began working on an undercover operation to ensnare him in a crime in an effort to force his cooperation if he didn’t give it willingly.

After covering this case for decades now, I am left to wonder if this is an endless cat and mouse game between the FBI, which remains in sole charge of the investigation, and those who may have information on the whereabouts of the masterpieces. A better approach might be to take a page from the extraordinary success of the Ice Bucket Challenge, which has used social media to raise millions of dollars for needed ALS medical research.

Why not promote a similar social media campaign using trusted figures, like Cardinal Sean P. O’Malley, who are respected in many segments of society — rich and poor, law-abiding and not — with the message that those paintings enrich all of us? Since the theft in 1990, Boston has changed; it’s become a world-class city and omertà is no longer the operating principle.

Those masterpieces by Rembrandt, Vermeer, Degas, and Manet belong back in the museum for all of us to appreciate and be inspired by, just as Mrs. Gardner intended in collecting the art and opening the museum in 1903.

Although the FBI remains mum about the status of the investigation, the mystery surrounding Bobby Gentile’s involvement remains a reminder that a new approach might be worth considering.


In my final interview with him in his home in 2019, Gentile waved off all suggestions that he could provide a path to recovering the art, laughing when I suggested that perhaps the paintings actually had been damaged beyond repair when buried beneath his shed, and his extreme embarrassment sealed his silence.

Gentile’s lawyer, McGuigan, is convinced he died knowing nothing substantive about the case. Not long after my 2014 interview with him, Gentile got enmeshed in a second FBI undercover scheme and wound up back in jail — where he fell ill and appeared to be on his deathbed. McGuigan rushed to his side with a plea: Just tell the authorities what happened to the paintings. The reward for their return is $10 million, even if they’re damaged. I’ll have you home tomorrow.

Gentile rejected the offer.

“They could make the reward $100 million and it wouldn’t change anything,” he said, “because there ain’t no paintings.”

Stephen Kurkjian, a 40-year veteran of The Boston Globe who retired in 2008, is author of “MASTER THIEVES: The Boston Gangsters Who Pulled off The World’s Greatest Art Heist.” He can be reached at