The Great Art Heists of History: The Robbery of the Isabella Stewart Gardner Museum, Part 2: The Investigation


FBI agent Thomas McShane has been tasked with investigating a potential suspect: Whitey Bulger. Bulger was well known to the local authorities. He was the head of Boston’s notorious Winter Hill Gang, one of the city’s most powerful organized crime families. The Irish-American thug was also familiar to the FBI, and not just because of his “job title.” Whitey had been playing both sides of the field since the mid-’70s and was actually one of their informants – though the cunning rat would never admit it. His relationship with the Boston Police Department would certainly have given him access to legitimate police uniforms, and the sounding of the fire alarm matched the business card of the IRA – an organization with which old Whitey was known to have connections. But no matter what his gut told him, the evidence just wasn’t strong enough. Everything was circumstantial at best.

In April 1994, Isabella Stewart Gardner Museum Director Anne Hawley received a letter from an anonymous sender. The mysterious letter claimed that its author was a third-party negotiator who did not know the identity of the thieves, but could disclose that the motive for the theft was to reduce a prison sentence. The sentence had now passed the stage of mitigation, and subsequently the thieves wanted to negotiate the return of the stolen artwork – which was safe in a climate-controlled environment. The return conditions were straightforward. The thieves wanted full immunity, as well as $ 2.6 million to be paid into an offshore account, with the transaction taking place at the time of handing over the art. If the museum accepted the stipulated conditions, it had to print a message coded in The Boston Globe. The letter had seemed legitimate. The writer had included information that only the authorities and the museum knew about. Hawley contacted the FBI, and on May 1, a coded message was printed in the World. Hawley received a second letter several days later, but it appeared that the people behind were starting to get cold feet. The letter expressed that they needed more time to figure things out, and Hawley never heard from the enigmatic writer again.

Robert ‘Bobby the Cook’ Gentile

Previous investigations may or may not have been simply cases of bad tree barking. In the years since the brazen heist, the Federal Bureau of Investigation has devoted more time and resources to one particular criminal organization – the Boston Mafia. On September 17, 2021, one of the last suspects in the Isabella Stewart Gardner museum burglary died: Robert “Bobby the Cook” Gentile. Originally from Connecticut, Gentile was a well-known association of the Merlino gang, a branch of the Boston-based mafia that swore loyalty to boss Frank Salemme. Gentile was also close to another Merlino associate, Robert Guarente. Guarente was buried by cancer in 2004, and the Bureau was contacted in 2010 by his widow, Ms. Elene Guarente. She said when her husband fell ill with cancer in the early years, he gave the stolen paintings to Gentile for safekeeping. Naturally, Gentile vehemently denied the allegation. He was indicted in 2012 on drug charges, which may or may not be a ploy on the part of the Bureau to obtain information regarding the Gardner Heist. He underwent a polygraph test and, denying any knowledge of the theft and location of the stolen artwork, the results showed he was lying. Furious, he insisted he was being completely honest and demanded that another test be done. This time around, he claimed that Guarente’s widow had once shown him Rembrandt’s stolen self-portrait, with the polygraph indicating he was telling the truth. This could indicate why the first polygraph test showed Gentile knew the location of the artwork, but his lawyer intervened, protesting that the high number of federal agents present had affected the test result, and he requested that his client be interviewed in a more intimate manner. The request was granted but Gentile has always denied any knowledge of the breakage.

Now armed with a search warrant, officers stormed Gentile’s property in Manchester, Connecticut. Although no tangible evidence was provided during the search, a “secret ditch” was discovered under a false floor in the garden shed, and in the basement they found a copy of the Boston herald of March 1990, which reported the theft, as well as a piece of paper that listed the potential sale value of each of the stolen parts. Gentile’s son said everything his father stored in the shed had been destroyed by flooding several years before, leaving him visibly upset at the time. Asked about the list of stolen works of art, Gentile explained that it was written by a criminal who was trying to organize their return from Guarente, and that he had only acted as an intermediary. Although the evidence was not strong enough to charge Gentile with involvement in the theft, he was still jailed for 30 months on drug trafficking charges. He never offered any further information about the heist. If he had, his sentence would certainly have been reduced.

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