Southie Tears on the Day Whitey Bulger Died

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Why you should care

Death, time and perspective sometimes change things. And not always for the better.

In this occasional series, OZY takes to streets and neighborhoods across the globe to ask a simple question: “How was your day?”

Anna Weeks

On Oct. 30, 2018, the day 89-year-old mob boss James “Whitey” Bulger died, there were tears. The tears were shed by women in Boston for this killer of at least two women. While the families of his victims were rejoicing over Bulger’s murder, along with plenty of other people sickened by his crimes, Anna Weeks, wife of Bulger lieutenant Kevin Weeks, felt differently about the demise of Southie’s most infamous resident.

It’s important to remember that during the uproar over busing in the ’70s, the Bulger family had a powerful impact on both sides of the community. William Bulger, Whitey’s younger brother, was a fierce opponent of busing and had become a state senator at the same time that Whitey was head of the criminal underworld.

While most Americans believed in the president of the United States, many in Southie believed in Mr. James Whitey Bulger, or Mr. Jimmy, to some. They believed he kept the real bad people out of Southie, along with the bad drugs. Things got so much worse when he went on the run; that’s when all those teenage suicides took place.

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James “Whitey” Bulger, aka Mr. Jimmy to friends in Southie.

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Everyone knew Whitey and the boys. Most feared them, some relied on them and some worked for them — but, like it or not, they were all better off with them around. The women’s deaths were tragic, and there is no denying that. I just don’t think Whitey sought out women to kill or wanted that to happen. But he had to make sure things went smoothly.

I have to get my point across, though, no matter how much many will disagree with me … in some ways, the town was better with Whitey.

His associates knew the rules: Women were to be left in the dark about business, and you didn’t have sexual relations with family members. It was one of his associates, Stevie Flemmi, who made poor choices and did not abide by that rule. Stevie’s actions left Whitey no choice. There is no way I can excuse what Whitey did, but perhaps he couldn’t leave it up to Stevie to kill those two poor women without his supervision. I simply do not know.


Whitey had no problems with younger women if they cheated on him, or if he felt they were going to hinder his reputation. He simply told them to scram. Moreover, the young women Whitey dated were street smart, and in some ways he saved them. He paid for many of them to attend private schools during busing and afterward. Yes, of course, I understand it was wrong for him to have affairs with them. They were young but not innocent.


Anna Weeks on her wedding day.

Source Courtesy of Anna Weeks

Whitey was always waiting for my friend Patty from St. Brigid’s and Cardinal Cushing High School to come out after class. The minute she walked out the door, she would hike up her skirt and undo a few buttons on her shirt and hop into the expensive car Jimmy had parked outside the school. They’d usually go shopping and she’d come into class the next day with a really gorgeous, expensive pair of shoes.

I was so jealous. I don’t know if they had sex or anything, but I do know he paid tuition for a couple of other students and helped their families pay their rent. 

I have to get my point across, though, no matter how much many will disagree with me, that I will always believe that in some ways, the town was better off with Whitey and his associates. Once he was gone, the condos pushed families out of their homes, drugs like heroin soared and family businesses couldn’t afford to pay rent anymore.

When Kevin and his first wife went out with Whitey and his girlfriend of 30 years, Teresa Stanley, they always went to expensive restaurants and ordered lobster and the finest wines available. Whitey loved to sing around the piano bar and just relax and have a good time out with his favorite girl. He would be a perfect gentleman to anyone he met in the restaurant, often sending over expensive bottles of wine to people he had chatted with.

It’s just hard to put that image together with the one where he killed two young girls. So I just don’t do it.

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