Kevin Cullen

Jeffrey Epstein and ‘Whitey’ Bulger: A tale of two sociopaths

Jeffrey Epstein (left) and James “Whitey” Bulger.
Jeffrey Epstein (left) and James “Whitey” Bulger.Left: New York State Sex Offender Registry via AP, File/Right: US Marshals Service via AP

At first glance, Jeffrey Epstein and Whitey Bulger appear to have nothing in common.

Epstein, a Brooklyn Jew, was a New York financier who rubbed elbows with billionaires and presidents, and sometimes those two things were the same thing.

Whitey was an Irish Catholic project rat from South Boston, an old-school gangster who liked fast cars and faster women.

Epstein worked in banks. Whitey robbed banks. But those superficial religious, ethnic, geographical, and vocational differences cloak striking parallels.

They both grew up in working-class families where money was tight. Epstein’s father was a landscaper for the parks department, his mother a school aide and homemaker. Whitey’s father was disabled, having lost an arm in a railway accident, his mother a homemaker who at one point worked as a clerk typist at the Registry of Motor Vehicles.


Neither Epstein nor Whitey had a college degree, but they were deviously smart, in ways that you could never learn from a book. They were master manipulators and knew how to get people to give them things. And when people wouldn’t give them things, whether it was money or sex, they’d steal it.

Whitey made money by stealing it at the end of a pointed gun. Epstein, according to a business associate, made money by stealing it with a pen and a computer.

They could be charismatic and charming and were invariably cunning and malevolent. They both had a predilection for young women, even girls.

As they committed myriad crimes and ruined lives, both men believed their own conceit, that they were not criminals but government assets. Epstein claimed he was an intelligence agent. Whitey was an informant for the FBI, but insisted he was only milking the feds for his own purpose.

Both men were allowed to engage in reigns of terror because the federal government protected them, for selfish, cynical reasons. The FBI used Whitey, even though he gave them little, to get the bugs they needed to take down the Boston Mafia, and in return helped him bump off anybody that might expose their sordid relationship, looking the other way as he murdered rivals and potential witnesses.


Epstein should have been in prison for raping girls. The feds gave him a sweetheart deal and he did easy time like one of the wiseguys in “GoodFellas,” serving what was more akin to after-school detention than a federal prison sentence.

After exploiting everything and everyone, making millions and, in Epstein’s case, billions, both men died as guests of the nation, with either the abject incompetence or sinister connivance of a government that once coddled them.

Whitey was murdered in a West Virginia penitentiary, after some people in the US Bureau of Prisons engaged in careless or malicious thinking, reclassifying him as healthy enough to move to a more dangerous prison, where gangsters from Massachusetts who didn’t like stool pigeons awaited. Epstein allegedly hanged himself in his New York cell, under circumstances that, like Whitey’s, seem so egregious that you’d almost think that it was a setup, that either the government didn’t care if he died or, if you’re partial to conspiracy theories, had a role in it.

When assessing criminals, there is a propensity to create hierarchies of victims. So it would seem that Whitey Bulger was the worse human being, given that he murdered so many people, a number of whom he buried in shallow, secret graves, depriving their loved ones of closure. But it is clear that Jeffrey Epstein murdered the souls of countless young women and girls. He was a sick man who destroyed lives while being embraced by the rich and powerful, as if part of a club for which there was nothing that merited exclusion.


Jeffrey Epstein and Whitey Bulger were sociopaths, devoid of empathy, obsessed with their own venal needs.

All the more reason to learn how they died, lest we become like them.

Kevin Cullen is a Globe columnist. He can be reached at cullen@globe.com. Follow him on Twitter @GlobeCullen.