But gentrification has its limits, and no amount of shops, sleek taverns and family-friendly eateries can change the mind-set of a population attached to its past, even if that past was defined by a man now in federal custody and linked to 19 murders.
"He was just that tough guy, that guy that everyone here wanted to be," said Teresa Needle, summing up the conflicted feelings of longtime locals as she strolled up West Broadway on Saturday, three days after Bulger's arrest in Santa Monica after 16 years on the run.
"I think some people are very happy he's finally been apprehended, but I think others who are loyal to his past are kind of sad," said Needle, who declined to say which side she came down on.
But she added with a tinge of wistfulness: "He got caught. That wasn't his style."
Bulger, 81, was brought to Boston on Friday along with his longtime girlfriend, Catherine Elizabeth Greig, 60, who FBI agents said proved the key to his capture.
In Bulger's former neighborhood, horror at the crimes prosecutors accuse him of committing is mixed with a certain respect for his ability to evade justice for so long, and for the way he provided for loyalists. It's a feeling far more prevalent among longtime residents than the newcomers who are slowly turning the area around. Like law enforcement officials who hunted Bulger and his Winter Hill Gang, they wonder how it's possible to speak fondly of someone with such a brutal past.
"Most of those people never knew him or what he did," said Richard Baker, a retired FBI agent. Baker said there was a cult that grew up around Bulger but that wasn't around when he was running the Winter Hill Gang and ordering hits: "They didn't understand the evilness of the man."
Everyone in South Boston, it seems, has a Bulger tale. Taken together, they reflect the changes in the neighborhood, where new, glassy buildings occupied by young professionals and families soar above squat pubs and delis. On the streets, joggers stroll past weary-looking old-timers puffing on cigarettes and missing the old days, even as they acknowledge the bad parts.
Joyce Jones says Bulger had an eye for her younger sister when they were teenagers, and she swears she spotted him walking through a nearby housing project a few weeks ago.
Joseph Collins says he was a kid when Bulger was a grown-up gangster. "He was quite a guy. I liked him," said Collins, who owns a bar on a corner that once housed a Bulger hangout.
Linda Castagna, who owns the upscale Urban Exchange furniture shop where a bar once stood, says her husband's brother's friend's father was killed by Bulger.
A woman from New Jersey named Jamie gave birth to a baby the day Bulger was arrested, watching the news in her hospital room with her husband.
They didn't move to Boston until well after 1995, when Bulger — tipped off by a corrupt FBI agent — vanished before he could be arrested. "But you couldn't not hear about him," she said while nursing her newborn daughter in the courtyard of an old stone church that is now a condominium complex.
For one thing, his brother, William Bulger, was a leading state politician and president of the University of Massachusetts. In addition, Whitey was considered the king of Boston's mobsters. "He was kind of the only one, or the biggest one," said Jamie, whose husband signaled the ghost of Bulger's presence, even among relative newcomers, when he warned his wife against giving her surname.
The couple quickly went inside as a friend, Michael Whited, explained. "There's still a lot of fear around here," said Whited, though he wasn't afraid to express his disdain for the likes of the Winter Hill Gang.
"The murders, the drugs and absolute corruption," he said, attributing Bulger's ability to evade justice for so long to officials who were afraid that he would spill the beans on their corrupt dealings. "Everyone knew someone who got something."
Maybe so, but that's why Bulger had fans, explained Jones. "Let's say I needed something. He'd get it," said Jones, a self-described project girl who spent her youth hanging around outside the rough-and-tumble public houses on D Street. Whitey was a generation older and held court at a deli nearby
To hear Jones tell it, Bulger liked young women and lavished gifts on them: a Coach bag, Prada shoes. Jones says he provided a washing machine and dryer for her first apartment, even though she never dated him.
"We just knew them as regular people," Jones said of the gang. "We didn't know they were killers and thugs."
Collins, sweeping the sidewalk outside his bar, doesn't pretend to have been ignorant of the past. He just preferred to stay out of the fray and remain on Bulger's good side. Like other old-timers, Collins credits Bulger with preventing South Boston from being flooded with heroin in the 1960s.
"If he found out you were dealing, you were going to pay," Collins said, referring to the myriad ways the Winter Hill Gang was known to thrash its enemies, including strangulation and stomping them to death.
Others say Bulger merely controlled the heroin trade and steered it toward other areas.
"He had such control over this community," said Castagna, who said no matter how many horrible things you heard about Bulger, there was always someone with a "nice" story to tell about him.
Such as the time Bulger overheard a young thug bragging about having stolen computers from a school. Shortly afterward, he took the kid for a ride in his car. "And next thing you know, all those computers were back in school," she said, repeating Bulger lore that may or may not be true.
Whatever the truth, Collins said some things are clear. "A lot of guys wanted to be just like him but didn't have the guts," he said. "It made life really interesting in South Boston."
"He had such control over this community," said Castagna, who said no matter how many horrible things you heard about Bulger, there was always someone with a "nice" story to tell about him.
Such as the time Bulger overheard a young thug bragging about having stolen computers from a school. Shortly afterward, he took the kid for a ride in his car. "And next thing you know, all those computers were back in school," she said, repeating Bulger lore that may or may not be true.
Whatever the truth, Collins said some things are clear. "A lot of guys wanted to be just like him but didn't have the guts," he said. "It made life really interesting in South Boston."