By Sharon Oliver
Contributing Writer
BOSTON – There are thousands of small dive bars scattered throughout the U.S. that are notorious for not only good times but served as places for back room deals and clandestine meetings. One such watering hole was The Dugout Café on Commonwealth Avenue in Boston, which closed in early 2026, and was a favorite to many including Red Sox fans and also to two members of an infamous crime group who were the subject of books and four movies.
Prohibition ties
Allegedly, The Dugout started out as a speakeasy during Prohibition and has been a haven for anyone from sports players to students to professors to career criminals. Interestingly, the former establishment did not accept credit cards or have air-conditioning, yet it remained a popular hangout spot for decades.
The Dugout was initially owned by a former bootlegger, and racehorse owner who was so well connected it was said that he swayed elections and even punched Governor Maurice Tobin for refusing to help out a friend. His name was Jimmy O’Keefe. In 1941, a fight broke out in the Dugout, resulting in prison sentences for the two patrons. The next year, the Boston Health Department briefly closed the Dugout as part of a citywide crackdown on nightspot code violations following the devastating Cocoanut Grove fire that claimed the lives of 492 people.
Brink’s robbery
But in 1950, two of The Dugout’s most loyal customers would attain national notoriety when they took part in what was then the biggest heist in American history. In January of that year, Adolph “Jazz” Maffie, Joseph “Specs” O’Keefe (no relation to Jimmy), and nine other men wearing Halloween masks and chauffeur’s hats robbed the Brink’s, Inc. armored car depot in Boston’s North End, escaping with more than $2.7 million.
The Great Brink’s Robbery had the FBI stumped for almost seven years and was dramatized in several movies including the 1978 film “The Brink’s Job,” starring Peter Falk and Peter Boyle. Of the eleven people involved in the robbery, eight would receive life sentences, with two others dying before they could be convicted. Less than $60,000 of the stolen money was recovered. At the time, the robbery was considered to be the Crime of the Century.
The late Frank Kennedy, a longtime Dugout bartender, used to point to the corner booth where the Brink’s robbers planned the heist, allegedly. The crooks were also said to have met in a back room for privacy. Furthermore, it is documented that Maffie and “Specs” knew Jimmy O’Keefe and Maffie even used Jimmy O’Keefe’s restaurant at Boylston Street and Massachusetts Avenue as his alibi.
Maffie’s wife even testified that she was having dinner with her husband there when the robbery took place. However, the jury did not believe her and a postal worker later told the Boston Globe he remembered seeing Maffie and his bodyguards at The Dugout. Jimmy O’Keefe himself was arrested at The Dugout in 1961 after Boston police tried charging him with using a payphone in the bar to run numbers.
Shelter during Blizzard of ‘78
When over two feet of snow fell over the city during the Blizzard of ’78, The Dugout graciously opened its doors to provide shelter for weary fans who were unable to travel home due to dangerous weather conditions after watching a hockey game at the Boston Garden. Former Boston University sports information director Ed Carpenter recalled in Boston Magazine: “We get to Commonwealth Avenue, and we stop at Marsh Chapel, and Jack Parker says, ‘Anybody who wants to get out and go into the chapel and pray may do so.’ Well, half the bus got off, but they weren’t going to Marsh Chapel. They went across the street to The Dugout. The bar was their home for a week.”
The Dugout is now closed, but its countless memorable stories will live on.
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