Before there was a South Boston waterfront, these legendary spots set the stage

With the Atlantic Beer Garden and Whiskey Park torn down on the South Boston waterfront and more glamour and glass moving into their place, it’s important to look back at the establishments that paved the way for dining in this area, fine and otherwise. As P.J. O’Rourke once wrote, “Fish is the only food that is considered spoiled once it smells like what it is.”

When Jimmy Doulos first opened Jimmy’s Harborside restaurant in 1924, he probably wasn’t thinking that the lots around him would be used as gravel pits and parking parcels for the next several decades. Most likely he was thinking that having a seafood restaurant on the South Boston waterfront—the first of its style and kind—was a good idea and perhaps that it would spur others to move in next door in no time.

In many ways Doulos was right. Or at least he would be in the long term. Jimmy’s, which first opened as the Liberty Cafe and was eventually renamed after its owner, had little competition until 1963, when Anthony’s Pier 4 was opened by restaurateur Anthony Athanas. Jimmy’s stayed open for business for 70 years, and everybody seemed to know about it—from celebrities to customers from nearby Southie—despite the surrounding desolation, but perhaps due to its proximity to downtown Boston, Anthony’s eventually became the restaurant of choice on the waterfront. At one point, it was said to be the highest grossing joint in the country.

Boston being Boston, politics being politics, and conflict being conflict, Jimmy’s—and then Anthony’s, though with different specifics—closed in the crosshairs of a Massachusetts Port Authority bent on redeveloping the Boston Fish Pier and the surrounding areas. Meanwhile, if venturing over the Northern Avenue Bridge back in the day was an adventure you’d only dare to embark on for lobster and scrod, these days there are literally tourist traps and high-end eateries connecting Atlantic Avenue to the old gravel pits.

At any rate, much of the South Boston waterfront property where Jimmy’s was located was owned by the Pritzker family from Chicago. For years, they were in the middle of arguments over how best to develop the area. Very little got done. Until the Moakley Courthouse opened, followed by the ICA, followed by dozens of liquor licenses that magically appeared in a city where there are only so many such permits available. New corporate ownership, land swaps, and so on.

Jimmy’s, which would have turned 95 this year, closed in 2005. Legal Seafoods, once a tiny one-off that reawakened Cambridge in the early ’70s, opened a successful spot in its place.

Looking back, at least anecdotally speaking, locals seem to teeter in Jimmy’s favor. Perhaps it’s the name, or that Anthony stayed past his place’s natural expiration, while Jimmy knew when to call it a day.

Parts of this throwback have been previously published by Dirty Old Boston. This Dirty Old Boston feature is a collaboration between DigBoston, the Boston Institute for Nonprofit Journalism, and Dirty Old Boston. For more local history visit binjonline.org and dirtyoldboston.com.