By all accounts Paul Duffy was a man who cared deeply for his neighborhood, spending a lifetime living in, talking about and investing in the South End.

“He was very much a neighborhood, gregarious character. I guess that’s a good word to use. He was definitely a South End character known by lots of people,” said Ted Pietras, who was a good friend of Duffy for 40 years. “And everybody, you know, everybody liked Paul. Some people loved Paul. You know, Duffy was a good guy.”

Duffy, as he preferred to be called, passed away peacefully on December 14 at the age of 86, surrounded by family and loved ones.

Pietras said that Duffy often held court on a bench outside the South End Buttery, a part of the building he owned on Clarendon Street, using the time to talk with neighbors and friends as they passed by.

He invested in neighborhood real estate and restaurants, like Picco and The Beehive, for a time ran his management company and engaged in numerous neighborhood organizations all amounting to a very tangible impact on the South End.

Mario Melendez met Duffy in 1980s, shortly after he moved from Venezuela to pursue an engineering degree.

Melendez was looking for an apartment and was told by a friend to go see Duffy, who worked at Street & Company at the time.

“There was one, 78 Philips Street, that I liked. It was small, one very small bedroom. But the price was in the range of what I was looking for. So, he ended up cosigning my rent, my contract,” said Melendez. “Within a week, maybe 10 days, I was having dinner at his house.”

The two maintained a strong friendship for decades, with Melendez working for Duffy at his management company, O’ryan, Lopez, and Chin. Melendez took over after Duffy retired.

He remembers Duffy as a hilarious man who always had a joke. He’d often end a conversation by saying, “don’t forget what I told you.” When they’d look bewildered, wondering what they’d been told, he’d say, “well you forgot already!”

Stacy Koepell remembers that joke as well.

She and Duffy had first met during her tenure as executive director of South End Business Alliance. She credits Duffy as instrumental in having the Ellis South End Neighborhood Association, of which he was a founder and decades-long member, hire her on.

But more than anything, they were close friends, she said, adding that Duffy was more than proud she chose to raise her two sons, now 26 and 24, in the city.

“Paul showed up over and over again for neighbors, for causes, and for the South End. He was the kind of man who didn’t need praise, though he would absolutely pretend not to hear it anyway,” she wrote in a message she shared with The Boston Guardian.

The Guardian’s Editor and Publisher, David Jacobs, was a longtime friend, enjoying his company for over 25 years. Jacobs described him as jovial and kind, “an entity in very short supply, these days.”

Jacobs recalled a story from when Duffy had gone to London either to see a Patriots or Red Sox game and found himself speaking with a bellhop who had desperately wanted to see the game. Duffy gave up his ticket so that the bellhop could go.

“He was always, always, thinking of other people. He never, ever, asked for anything in return,” said Jacobs.

Duffy had a deeper institutional knowledge of the South End than most anyone, growing up on neighborhood streets that had at a time perhaps not been terribly safe to walk alone at night. He even remembered a time, according to a 2024 Boston Guardian story, in the 1940s when he was a young boy, where South End neighbors had to ask area brothels to paint their lintels red, as they were fed up with Johns knocking on their doors in the middle of the night.

Duffy used that knowledge to help better his neighborhood and his time he watched, and himself invested in, a future come that would see its reputation changed.