BEFORE THE BELL

His earliest memory of Southie is “bombing down” Ticknor Street on a Big Wheel at three years old, being pushed by his cousin Guy.

Calogero LoGrasso, also known as Charlie, grew up on the corner of L Street and 8th Street. The son of immigrants, his parents moved to South Boston from Riesi, Sicily, in the 60s, and the family has been leaving their mark on the town ever since.

His uncle Sal owns Sal’s Ristorante & Pizzeria across from L Street Tavern, his uncle Ottavio owns Ottavio’s Barber Shop on W. First Street, and his brother Sal owns LoGrasso’s Barber on West Broadway.

While LoGrasso himself might not have his own Southie storefront, his legacy lies in the gym of the L Street Bathhouse, now known as the Curley Community Center.

ROUND 1 – THE BEGINNING

The City Point Sicilian first picked up the gloves in grade school. The name pays homage to his roots, both in Italy and Southie.

He started training in November 1986. Four months later, he had his first fight at the Lowell Memorial Auditorium in the 1987 Golden Gloves Tournament – the pinnacle of amateur boxing.

The rookie fighter ended up winning the tournament, despite not having much experience.

According to his trainer, he was a natural.

The proof is in the pudding – or rather, in the second Golden Gloves title that he won in 1996.

From there, he went pro. And this past August, almost 30 years later, he became the oldest professional boxer in New England.

ROUND 2 – GOLDEN GLOVES OR GOLDEN GLOBES?

Although he still boxed recreationally, LoGrasso took a break from boxing professionally over the last three decades.

After he won the Golden Gloves, he moved to Los Angeles to see what it would be like to live outside of Southie and to train at one of the best gyms out there.

While he got plenty of reps in and made great friendships with people like former professional boxer Freddie Roach, he found something he didn’t even know he was looking for.

“I always loved writing and I loved plays and movies,” LoGrasso said. So, whenever he wasn’t in the ring, he was sitting a few rows back in the theater.

The first play he saw out in Los Angeles, ironically enough, was about two brothers from South Boston. He couldn’t help but think he could’ve written the story better…and later that night in bed, he decided that he would.

LoGrasso prepared for this next venture as he would for a fight, with research and hardwork. He got his hands on every possible screenplay and read them. He once even wrote 100 pages in 48 hours!

Fast forward to this past May. He won Best Original Screenplay at the Indie Vegas Film Festival for his Boston-based film Shannahan, where a gang of thieves find out the hard way that making easy money doesn’t always come easy.

At that point, over the past five months he had earned the titles Nonno, after his first granddaughter was born, and Award Winner, for the screenplay. But hey, what’s one more?

ROUND 3 – RUNNING IT BACK

Two years ago, LoGrasso was with his uncle and cousin on Castle Island when he told them he wanted to make a comeback. They responded with laughter, told him he had a potbelly and to just go to the L and relax.

“I’m 57, not 87!” LoGrasso said. “Come to the gym and I’ll show you.”

The City Point Sicilian had more fight in him and wasn’t ready to hang up the gloves for good.

“The first thing to go for a fighter is his legs…I still got my legs. I run the island, I run like Forrest Gump,” He said. “I got really good wheels still! And I can punch. So, I said why not give it a shot?”

And give it a shot, he did.

On August 16, 2025 he went against a 26 year old fighter. When he first found out he was going up against someone that age, he thought, but I’m a nonno! Then, his mindset shifted to, I’m a nonno and I’m still doing what I did when I was 18.

He had his pre-fight pasta lunch (bucatini, ziti, linguine, it doesn’t matter), made the sign of the cross and then he was ready to go. As for the nerves, there were none. After all, he had 30 years to shake them off.

“I try to just do the work so I know I’m ready. I used to be nervous, those days are over,” he said.

After the final bell rang, it was official. He won.

Charlie LoGrasso, the City Point Sicilian, was now the oldest professional boxer in New England history.

THE FINAL FIGHT

But…he’s not done with the sport that gave him so much.

You heard it here first…he wants Bobby Lights Out Laing.

Who is Bobby Lights Out Laing?, you might be asking. He’s an amateur boxer often highlighted on Barstool Sports’ Rough N Rowdy show. It would be the ultimate South Boston vs. South Shore showdown between two fighters with very different styles.

LoGrasso wants that to be his last fight before he focuses on making films and spending time with his daughters.

“[Boxing] is the greatest teacher in the world,” LoGrasso said. “Nothing – aside from growing up on the streets of South Boston – has taught me more about life.”

Who knows…in another 30 years, he could be saying to his cousins, “I’m 87, not 107! Come to the gym and I’ll show you.”