Paul R. Flanagan—known to everyone simply as “Flan”—of Squantum and Naples, FL, passed away leaving behind a reputation, a thousand stories, and more one-liners than anyone could ever keep up with.

Born in Boston, Paul was the son of the late Joseph and Ruth Flanagan and brother to the late Joseph “Joe” Flanagan. He grew up in Squantum, where friendships lasted a lifetime, and attended North Quincy High School, Class of 1963. Before graduating, he enlisted in the United States Marine Corps during the Cuban Missile Crisis—a decision that defined the kind of man he was.

A Marine’s Marine, Flan served in Vietnam as a squad leader with Company D, 1st Battalion, 3rd Marines. In 1966 near Da Nang, he led his men under mortar and sniper fire, maneuvered them into position, and directly engaged enemy forces—destroying an enemy boat with a grenade launcher and leading actions that accounted for multiple enemy casualties. He was awarded the Purple Heart and the Navy Commendation Medal with Combat “V.”

And he never talked about it. Not the war, not the medals, not what he did. If it came up, he’d brush it off or change the subject. That was Flan—did extraordinary things and acted like it was nothing.

After returning home, he joined the Teamsters Union and worked in the newspaper industry with the Boston Herald and Boston Globe. But his real life’s work was the people around him.

Flan was a presence—whether in Squantum, Quincy, or anywhere he walked into. Always in his scally cap (and if it was missing, you’d hear “Where’s the Flan cap?” immediately), always with that grin, always ready with a perfectly timed line. His sarcasm was sharp, his humor effortless, and his one-liners became part of everyone else’s vocabulary.

He was a devoted father to his son, Dave Flanagan, and a proud father-in-law to Melanie, the daughter he never had. He was the loving grandfather of Riley, Joe, Shea, and Hannah, and great-grandfather to Lola.

He adored all of his grandchildren—but Hannah held a special place in his heart. He was endlessly proud watching her pursue her sports broadcasting career, following along in complete awe of what she was doing. Once he finally figured out how to pull up her videos on his phone, he watched them like it was must-see TV, beaming with pride every time.

Flan loved fishing and lobstering in Quincy Bay, and deep sea fishing with his brother Joe. He loved being around people—whether it was Little League games, hockey rinks, or tournament weekends where he somehow became just as popular with the other parents as he was with the kids. Among friends, he also carried the legendary nickname “40 Beers Flan,” which, like everything else about him, was said with equal parts humor and respect.

He was a Frank Sinatra guy—and not quietly. Flan would sing the lyrics before Frank did, just to make sure everyone knew he was one step ahead.

People were drawn to him. His son’s friends, his grandchildren’s friends—everyone wanted to hang with Flan. He’d make fun of his son, then turn to his son’s friends with that grin and a laugh that would light up the room—pulling everyone in with him. Several men, both living and deceased, proudly called Flan their best friend—a title he carried without ever trying to earn it.

His house was always open. Boston Herald guys lived there at times and called it “Father Flan’s.” If someone needed a ride, a place to stay, or somewhere to go for the holidays, Flan was there without hesitation.

He was respectful, loyal, and steady—the kind of guy you wanted on your side. He would never start a fight, but if provoked, he would finish it. As one North Quincy classmate said, “Best left hook I’ve ever seen.”

Despite everything he had done, he never made it about himself. He took care of his mother, Ruth, until her passing at 96, and lived his life focused on others, not himself.

If he were here now, he wouldn’t want anyone making a big deal about him. He’d be asking how you’re doing, making sure you’re alright—and probably cracking a one-liner to lighten the mood.

Paul “Flan” Flanagan leaves behind a family and a community that will carry his stories, his humor, and his spirit forward. His voice will live on—in the sayings people repeat, in the laughter he created, and in every room where someone delivers a perfect line and everyone thinks the same thing:

“That’s a Flan line.”

His best friend Neco was by his side all the way to the end.

He never made it about himself—but he made life better for everyone around him. And that’s exactly how he would’ve wanted it.

Relatives and friends are respectfully invited to greet the family during the visiting hours on Friday 3/27/2026 from 4-8 PM in the McDonald Keohane Funeral Home SOUTH WEYMOUTH at 809 Main Street (Rte 18 opp. So. Shore Hospital). Burial will be private.