But Grace — who emigrated from Kilkenny to the States in 1960, serving a stint in the US Army, working in banking in New York City, and dabbling in the hotel business in Colorado before landing in Boston — saw great potential in this “little cubbyhole,” and soon grew to love it. And even though the building’s owners, the Abbey Group (the development firm famous for refurbishing the Sears building in the Fenway into the Landmark Center), drew up various plans over the years to turn the bar and adjacent garage into an office building and a hotel, those plans always fell through. So the Littlest survived to see another day, every day for 15 years.

Grace, with his Irish connections, helped fill the place with thirsty new arrivals to the city. And suddenly, a place O’Shea says was “going downhill a little bit,” was flush again. The famous and semi-famous stopped in. Musicians like Mary Black, Phil Coulter, and Sharon Shannon. Boxers Sean Mannion and Kevin McBride. Ray Flynn and Joe Kennedy. Quentin Tarantino, even. But the lifeblood of the place was the regular guys, say Grace. “Everyone from politicians to street cleaners to guys with no work.”

But now, it’s time to say goodnight. Paddy Grace doesn’t own the property. If he did, he’d stay open. He does own the name, and that all-important liquor license. And despite the fact that he could sell the latter for a tidy profit, he’s still trying to relocate, but only if he can find a smallish downtown space where the rent isn’t too dear. Even if he does, however, he knows nothing will be the same. “End of an era is perhaps too drastic,” he says. “But all you have to do is move a block and you lose your regulars.”

That hurts the most. Grace has seen smoking bans, and price increases, and creeping gentrification. He’s seen people come and go. But through it all, his little pub has been there. “There have been a lot of changes,” he says. “People move to the suburbs. Or back to Ireland, or England. Or they die. But people always come back — the ones who can — to say hello.”

The regulars
Sitting in the Littlest in the morning makes one feel like a man out of time. While professionals scurry to work outside, clutching the Tuesday New York Times and a Starbucks, people here start their mornings quietly with the Herald and a beer.

In walks one guy with red hair and a big nose, the map of Ireland all over his face.

“What can I do ya for?” asks O’Shea.

“Uh, a couple Buds.”


“Two Buds.”



He serves ’em up. The guy knocks ’em back. But these guys are hardly the hopeless sots you might think. They’re well-dressed, and well spoken. And this is their morning ritual, natural as a cup of coffee. A time to share stories. To shoot the shit. To talk about the news, and talk about the old days.

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