Kevin Cullen

In the end, everything has passed Whitey by

When the marshals drove him up Northern Avenue Monday, away from the courthouse named for his old neighbor Joe Moakley for the next-to-last time, it may have dawned on Whitey Bulger that he never got to set foot on the shiny new waterfront of his hometown, South Boston.

Among the crimes Whitey was convicted of was opening fire 31 years ago just down Northern Avenue, killing Brian Halloran, a hoodlum, and Michael Donahue, an innocent man who made the mistake of offering a ride home to someone Whitey wanted dead.

Back then, the Southie waterfront was a seedy, seldom-visited section of the city. On windy days, the smell from the fish processing plants in the Lower End wafted toward the waterfront. There were only a handful of decent restaurants — Anthony’s Pier 4, Jimmy’s Harborside, the Daily Catch — and the local bars were gritty gin mills.


Today, the waterfront glistens with new money and frenetic energy. Office and apartment buildings sprout up every year. Gleaming restaurants open every month. In the 16 years that Whitey hid in open view in Santa Monica, the Southie waterfront was reborn and rebranded as the Seaport.

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Louis, the most exclusive clothing store in the city and where Whitey bought some of his suits, decamped from fashionable Newbury Street in the Back Bay for the suddenly posh Seaport. Fan Pier even landed a museum, the Institute of Contemporary Art. Further down Northern Avenue, where Whitey Bulger slaughtered Halloran and Donahue on a warm spring night in 1982, every new restaurant seems to do booming business. The young people who pay as much as $3,000 a month for a nearby two-bedroom apartment don’t blink at paying $12 for a drink.

Whitey never got to have a $50 steak at Del Frisco’s, or to appreciate the view from the rooftop bar of Legal Harborside, or to figure out how to make money from the thousands of out-of-towners who flock to the huge convention center, and he never will. He’ll come back to court one more time, for his sentencing, which is almost irrelevant. Whitey Bulger will die in prison.

Of course, that’s better than he would have expected back in the 1970s, when there was a small, internecine gang war on in Southie. Whitey was so sure he was going to be assassinated that he went out and bought a fancy suit and hung it in his girlfriend’s closet. He wanted to look good in his open casket. Whitey used to shop on Newbury Street, shelling out $2,500 for a pair of R.J. Foley black alligator cowboy boots without batting an eye.

In a letter he wrote from jail, Whitey wondered whatever happened to that suit. Up until recent years, he probably could have still fit in it, with just a few alterations. Whitey was always obsessed with being lean and physically fit. It was important in his business, he told his protege, Kevin Weeks, to look taut. It intimidated other people so they’d give you money quick, no questions asked.


Whitey prided himself on being able to smell an extortion victim. They might have just come into money. Or maybe they had a weakness: a taste for liquor, or for women. Whitey would exploit any weakness, then put a knife to someone’s throat, or shove a gun in their groin, as he did to Mike Solimando, a businessman who made the mistake of trying to help the widow of a Boston businessman who Whitey and his gang had murdered. After Whitey’s threats to kill Solimando’s family persuaded Solimando to fly to Switzerland to raid the Swiss bank accounts of his dead friend, Whitey hissed a preemptory warning: “If you go to the FBI, I’ll know in five minutes.”

Which was true. Whitey had been enlisted by the FBI as an informant and quickly learned how to exploit that relationship. The FBI not only looked the other way while Whitey murdered, maimed, and robbed, but FBI agents compromised the investigations of honest law enforcement agents who tried to nail Whitey.

Monday’s verdict confirms all that, once and for all.

Whitey had mounted a legacy defense, in that he didn’t care about most of the 32 counts against him. In fact, he only cared about two of the charges — the murders of Debra Davis and Deborah Hussey — and something which he was not charged with because it is not illegal, being an FBI informant.

Whitey’s lawyer admitted that he made millions from the drug trade, even while his politically connected family in general and his politician brother in particular spent decades repudiating anyone who suggested Whitey lined his pockets with drug money.


Whitey was willing to admit to the drug dealing for two reasons. One, it would have looked pretty silly to deny it in the face of a parade of admitted drug pushers testifying that Whitey either put them in business or put a gun to their head and shook them down. Secondly, Whitey copped to the drugs because he hoped such candor would persuade the jury to throw him a bone and acquit him on some of the charges he found most repulsive, namely, the killing of the women. He was wrong again. The jury said he killed Hussey. Of Davis’s killing, the panel couldn’t decide.

Whitey spent his entire criminal career fashioning a narrative that portrayed him as a good bad guy, a criminal of principle, a wiseguy with scruples. But wiseguys with scruples don’t rat on their friends or strangle a 26-year-old woman and bury the body in a shallow hidden grave.

Now we know, beyond a reasonable doubt, that he did both.

He will deny it, for sure, when he stands to hear his sentence and gets to say his piece. And if I was Whitey Bulger, I also would have believed that I had immunity to do whatever I wanted, including kill people, because he did that for 20 years and the FBI aided and abetted him.

Of course, you’d have to be delusional to think a government agent, in this case a conveniently dead prosecutor named Jeremiah O’Sullivan, had the authority to hand out licenses to kill. But throughout his life, Whitey displayed a certain disconnect with society. He was a loner who wanted to impress strangers with his knowledge about arcane subjects. He never liked crowds, but always thought he was the smartest guy in one.

And for a long time, he was smart enough to enlist the nation’s premier law enforcement agency to serve as his accomplice while eliminating the competition, whether they were the big Mafia boys in the North End or monosyllabic Irish hoods in his Southie backyard.

As much as he didn’t recognize the new waterfront when the marshals drove him to his arraignment two years ago, Whitey wouldn’t recognize Broadway, either, east or west. Yuppies holding Starbucks lattes wait for the bus across from the sushi joint that used to be Triple O’s, the bucket-of-blood bar where Whitey plotted and sometimes killed.

From the Lower End all the way to City Point, the dark, dingy pubs where Whitey’s bookies sat in the corner, like sleeping dogs, have given way to bright, airy bars with French doors, where the point is to be seen, not hidden. They are bursting with young people, few of them Southie natives. At Lincoln, across from the West Broadway parking lot where Whitey read the newspapers every night at midnight, the kids don’t mind waiting on the sidewalk for a table. Pretty young women in fashionable running togs clog the Sugar Bowl, jogging around Castle Island, where Whitey walked daily with Kevin Weeks. The liquor store that gave Whitey a legitimate stream of income is now run by a Vietnamese guy.

For two months, as Whitey sat there and watched an absurd cast of criminals get up and point at him, all of them, the accused and the accusers, appeared to be visitors from another time and place. It was so blindingly obvious that none of them belonged in a neighborhood and a city where Whitey once ruled like a brutal dictator. Southie moved on. Boston moved on. Whitey only moved away.

The young diners and revelers who flirt at Whiskey Priest, the upscale pub near the spot where Whitey leveled his rifle at Michael Donahue and Brian Halloran, don’t even know who Bulger is.

And they don’t care. He is not part of their Boston.

He’s a ghost, not even dead yet, but a ghost.

Kevin Cullen is a Globe columnist. He can be reached at