By Ginger DeShaney

After 50 years at the helm of Harold’s Barber Shop, Harold Amato has hung up his scissors. 

This old-school Southie landmark at 87 L Street closed its doors on March 31. In a farewell ad to his customers, Harold wrote, “I have made several great friends and have many memories that I will treasure forever. It has been my utmost pleasure to be part of the Southie community … I will miss you all as I start the next chapter in my life.”

Harold, 77, of Marlborough, was the only barber in his shop for those 50 years. He never sat around; he was always on the go, which would explain how he could manage several customers at once.

He had tried other jobs as a young man, but none of them stuck. “I kind of liked cutting hair,” he said. “So I went that route.”

After getting his barber’s license, he started working for Mario’s Barber Shop. When Mario left the business, Harold bought it from him. 

The chairs, the mirrors, and even the cash register are as old as Harold’s business. 

He’s had quite a few customers who have been with him since the beginning. “One by one they are passing away or moving south,” he said. 

Harold estimates he probably had a thousand regular customers, including former Boston Mayor Ray Flynn. 

Mike Siaba, Harold’s brother-in-law, is one of the regulars. “I haven’t paid for a haircut in 30 years,” he laughed. “Some of the regular clientele, just like me, have been coming here their whole lives. They come in with their kids. It’s generations of people.”

The regulars have a connection here. “It hasn’t changed a whole lot. It’s an old-school kind of place,” Mike said.

People used to come by to just hang out. They’d maybe have a shot of whiskey, get some candy, shoot the breeze. But that changed because of the COVID-19 pandemic.

Harold’s business had been doing really well until COVID hit. “Last year was disastrous,” he said. 

When Harold opened back up after the height of COVID, people had to call to make an appointment. Up until the pandemic, people just walked in. 

In retirement, Harold has lots to do. He’s got a boat, sports cars, pets. 

“I’m excited,” Denise Siaba said about her brother’s retirement. “It’s been a long time driving in and out of Boston. He needs to enjoy himself.”

But he will miss the shop he’s called home for half a century.

“I met a lot of characters,” Harold said, including “Bulger and the rest of them.” Yes, Whitey had been a customer. “I didn’t cut his hair too many times. He was on the run,” Harold joked.

“I’ll miss some of the jokes, some of the talk,” he said, noting guys open up to him while they are in the chair. “I give advice sometimes.” 

Denise likened him to a psychologist. 

Tom Crowley, who has been a customer for 30 years, said this about Harold: “He’s a very special guy. For years and years he would stay open late once a month on a Thursday night to cut my hair and we would have a slice of pizza together. Sometimes work and family can get stressful. I work in the stock market, which is ultra stressful. Those haircuts were more like therapeutic sessions for me.”

Harold said he’ll also miss the gossip, the guys, the neighborhood. And the dogs … Harold always had dog treats at the ready.

But he will still be in touch with some of his regulars during retirement. He will make house calls to some of his older customers to cut their hair. He’s done that regularly if a customer was ill or had difficulty getting to the shop.

That’s just who Harold is: personable, caring, funny, customer-oriented. But he’s also got a devilish side to him.

“My dad [Vinny] also goes to Harold and he’s very close with him as well,” Tom recounted. “About 20 years ago I wrote ‘free haircuts for life’ in a birthday card for my dad. From that point forward every time I paid for my haircut I’d pay for his. Harold got a real kick out of this and used to tease me about it till one day I confided in him I never thought my dad would live this long, meaning I would have to continue to pay for these haircuts. So Harold, being the troublemaker that he is, went back and told my father what I said about him and the free haircuts and that I didn’t think he’d live this long. My dad didn’t speak to me for a month and Harold loved every minute of it. LOL.”

There are likely a thousand stories just like this starring Harold the barber. He leaves an indelible legacy on this neighborhood.

Harold Amato cuts Andrew Siaba’s hair.


Arnold Gatto has been getting his hair cut by Harold Amato for at least 20 years. “I like doing business with people in Southie,” Arnold said. “That’s what keeps Southie Southie.” Arnold called Harold a pretty sharp guy. “It’s great he’s retiring,” Arnold said. “He’s got his time in. We’re going to miss him.”

Mohmmed Forkan of Cafe Mamtaz is one of Harold Amato’s last customers on his last day at the barber shop.