The Littlest no longer has a men-only “tavern license” like it did until sometime in the ’70s. But stop in before noon and you’d be forgiven for thinking otherwise. Talk here revolves around boxing and politics, football and racing. Lawyers and unions and cops. The décor is in keeping with the virile vibe: dozens of patches donated by police and firemen from across New England and the country are affixed behind the bar. Framed black-and-white photographs hang in front of it. Joe Louis, fists clenched. Brownie, Bossuet, and Wait a Bit finishing in a triple dead heat at the Carter Handicap at Aqueduct in 1944. Muhammad Ali clowning around with a hurling stick at Dublin’s Croke Park. Babe Ruth, finishing his career in a Boston Braves uniform, meeting top-hatted James Michael Curley in 1935. Above the bar, in an incongruous bit of cheek, hang a fashionable line of Littlest Bar thongs.
Things are kept simple here. There are just two beers on draft, Guinness and Newcastle. If you want wine, you can order red or white. Whiskey comes in several varieties, including favorites from the auld sod like Paddy and Tullamore Dew. The jukebox has the staples. The Chieftains and the Dubliners. The Very Best of Joe Dolan . The Pogues’ Rum, Sodomy, and the Lash . There’s Johnny Cash and Patsy Cline, and U2 and Coldplay for the younger crowd that filters in later.
The floor is concrete. The ceiling, sturdy and simplistic, is made from weathered wooden slats. Tiny square lanterns (like you might expect to find swaying on a pirate ship) hang from it, glowing yellow with 25-watt bulbs.
The Littlest Bar was a different place when it opened in 1945 as much as a bookie parlor as a tavern, with heavy wagering on racing and fights. It was only open until 9 pm because its owner, a guy named Jocko, didn’t want undesirables getting sloshed and causing trouble.
“He was a piece of work, Jocko,” says Gene O’Shea, 73, rangy with snow-white hair, who’s been bartending here for 30 years and drinking here even longer — since 1952, when a beer was 15 cents.
Jocko’s wife took over for a spell after his death, and she was even worse. “She didn’t know how to run a bar,” remembers Jack, 84, a regular with a scally cap and big spectacles. “She used to order one bottle of whiskey at a time. Cheap too. She used to skimp on the pours, and look over her shoulder to see if you were looking.”
“She used to sit up there with the register,” gestures Phil, 74, ruddy-faced and rheumy-eyed, a trial lawyer who’s been coming here for half a century (and declines to give his last name). “She was like Madame LaFarge, playing with the knitting needles.”
A man named Peter Sheridan bought the place in the mid ’70s, and owned it for more than a decade before selling it 15 years ago to the current owner, Patrick “Paddy” Grace. Sheridan’s reasoning for the sale was simple: even then, there was the sense the place might not be around for long. Grace bought the place knowing this full well. “I knew from the very beginning that there were gonna be changes.”