The neighborhood has seen much over the decades. Irish gang wars in its streets, gentrification, decades of immigrants carving out new communities for themselves, and a future presidential candidate, Barack Obama, living in a basement apartment on Broadway.
Obama, whose sweeping oratory and increasing momentum could possibly lead him into the White House, lived at 365 Broadway in Winter Hill from 1988 to 1990 while he attended Harvard Law School.
In his two memoirs Obama lovingly describes many of the places he has called home, recalling the people and places that shaped him from Harlem to Hawaii to Indonesia. He never mentions Winter Hill and his legal education at Harvard gets little attention.
However it was during the time he lived in the three story brick building on Broadway that he first gained national prestige, began writing his life story and found his voice as a leader.
In his last year of law school, Obama became the first black president of the Harvard Law Review, one of the most exalted clubs at that esteemed institution and, for the first time, found himself in the media’s crosshairs.
“A burst of publicity followed that election, including several newspaper articles that testified less to my modest accomplishments than to Harvard Law School’s peculiar place in the American mythology, as well as America’s hunger for any optimistic sign from the racial front—a morsel of proof that, after all, some progress has been made,” wrote Obama in his 1995 memoir “Dreams from My Father.”
Book deals were offered and Obama, imagining he had something to say that the world should hear, accepted. In his last year of law school Obama, likely at least in part from his Somerville apartment, began to reflect on his life, craft its narrative and offer his voice to a national discussion.
“I began to organize in my mind, with a frightening confidence, just how the book would proceed,” he wrote in “Dreams.”
Though Winter Hill may have been the site for some of his growth as a leader, it is unlikely Obama, as a Harvard law student, had any extended contact with the Somerville community.
“I don’t think Barack was hanging around any of the bars on Broadway,” said Ward 4 Alderman Walter Pero. “Although he probably did shop at the Star Market.”
However, Obama could share at least one experience with today’s Winter Hill resident: the plague of parking tickets. When he left town in 1990 he left behind $400 in unpaid fines and late fees because of traffic violations in Cambridge and $72.63 in excise taxes and $45 in late penalties in Somerville.
Those fines went unpaid for almost two decades until in 2007, a few months into his campaign, Obama paid the fines and cleared his name as a scofflaw.
“The bus connections in Winter Hill were not as good in those days so that’s probably why he had to have a car and got all those tickets,” said Pero, who planned to vote for Obama on Tuesday.
It may seem unlikely that the man who has the best chance to become the nation’s first black president began to form as a leader while living in Winter Hill. Even today, decades removed from a murderous past, the neighborhood is best known to outsiders as a center of Irish organized crime activity.
An auto body shop on Marshall Street served as the headquarters for the Winter Hill Gang - a loosely organized group of criminals that became the top non-mafia gang in New England under the leadership of Buddy McLean, Howard T. Winter and eventually James “Whitey” Bulger. They etched out a place in the annals of criminal history by fixing horse races, gunning down enemies in broad daylight and corrupting the Boston office of the FBI (by the time Obama moved into the neighborhood in 1988 McLean was dead, Winter was in prison and Bulger had moved the gang’s headquarters into Boston).
However, city historian Bob Doherty said the immediate blocks surrounding Obama’s old home are steeped in presidential history. “As far as presidents touching that neighborhood there’s a lot,” he said.
William Howard Taft, history’s fattest president, came to Winter Hill to dedicate a federal park just a few blocks from 365 Broadway. When Taft arrived in the city a parade down Highland Avenue was organized in his honor, Doherty said.
And Abraham Lincoln, on a trip from Boston to Lowell, likely traveled through Somerville on boat in the since-filled Middlesex Canal that ran directly behind where 365 Broadway has stood since 1900.
Today those blocks are home to a variety of sub shops and bakeries that have become neighborhood landmarks and more recent Brazilian shops that cater to the neighborhood’s immigrant population.
In addition to shifting demographics the area hard by McGrath Highway and Mystic Avenue has also become more desirable to young professionals since Obama moved out in 1990. The 2007 sale prices of condominiums, single and multi-family homes in the neighborhood have almost tripled compared to prices just 10 years earlier.
Theresa Gallo has lived in the brick building Obama once called home for two years. She was surprised to learn the presidential hopeful had once lived there but said that would not pull her support away from another candidate.
“I’m voting for Ron Paul. I’m a libertarian,” she said.