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Kevin Cullen

Here’s no surprise: Whitey Bulger was a big Trump fan

Whitey Bulger and Catherine Greig, walking her poodles in Dorchester.File 1988/John Tlumacki / Globe staff / File

NBC News just published excerpts of letters showing that Whitey Bulger, the serial-killing South Boston gangster who is dead but won’t go away, was a big fan of Donald Trump.

Is anyone really surprised?

Did you think Whitey would have voted for Hillary? Or better yet, Bernie? Whitey had no time for feeling the bern, but he did hint pretty clearly at his political leanings early on when he torched John F. Kennedy’s birthplace in Brookline, aggrieved over the Kennedy family’s support for desegregation.

While he grew up in a household that benefited from liberal social policies and his brother was one of the most enduring Democratic power-brokers in Massachusetts, Whitey long ago turned his back on the Democrats.


The Bulger family lived in Dorchester, and the only reason they ended up in Southie is because Franklin Delano Roosevelt’s New Deal created a whole new thing called public housing. The family’s three-bedroom apartment at the Old Harbor projects was a marked step up from the cold-water flats they had inhabited.

But by the time Whitey was in jail, awaiting trial for all that drug-dealing and murdering that landed him in prison for the rest of his life, he was complaining about changes that he said had ruined Southie.

“Patriotism was a part of the neighborhood,” Whitey wrote in letters my colleague Shelley Murphy obtained. “Sadly, it’s changing. Rich people moving in, Moslems, illegals.”

Yes, before all the yuppies and outsiders of color, everything was just swell when Whitey and his henchmen were gunning people down in Southie, shaking down anybody and anything that moved, and sinking bodies in secret graves.

Whitey also got some notable help from politicians on the left. As he rose through the ranks of Democrats, becoming House majority leader by 1940 and House speaker by 1962, South Boston congressman John McCormack remained a huge ally for the Bulgers.


McCormack’s intervention helped Whitey secure an early parole after nine years in prison for bank robbery. So, too, did another prominent Democrat, the Rev. Robert Drinan, who before he became a congressman was Whitey’s spiritual adviser and his parole adviser.

While Democrats did much to help the Bulgers, Whitey turned on them when court-ordered desegregation of Boston’s public schools turned Southie upside down in the 1970s. In addition to firebombing the site in Brookline where President Kennedy was born, he underscored his resentment of Senator Edward M. Kennedy’s support for busing by spray-painting “Bus Teddy” on the sidewalk outside.

Whitey didn’t limit his violent resentment to politicians. He shot up The Boston Globe’s offices in Dorchester, furious over the newspaper’s support of desegregation.

And long before Donald Trump popularized the demonization of news media whose coverage he doesn’t like, Whitey was dismissing negative coverage of him as fake news. He got his politician brother and others to perpetuate the myth that he kept drugs out of Southie, while at his trial even his lawyers acknowledged he raked in millions while facilitating their distribution in the neighborhood.

Trump’s antagonism toward the news media is apparently what Whitey admired most. “Trump is tough and fights back instead of bowing down to pressure — and caving in to the press!” Whitey wrote in letters obtained by NBC.

Whitey also admired the way Trump handled his love life. “No way would he wind up in Oval Office with Monica Lewinsky,” Whitey wrote.


One major difference between Trump and Whitey is that while the president has a history of paying off women with whom he’s had affairs, Whitey had a different solution: He disappeared them.

One last irony: The politician who has done the most to find out why inmates were getting beaten and murdered with uncommon regularity at the West Virginia prison where Whitey was beaten to death is Eleanor Holmes Norton, congressional delegate for the District of Columbia.

I wonder what would bother Whitey the most: that she’s a Democrat, a woman, or black?

Columnist Kevin Cullen can be reached at cullen@globe.com.