With sixteen years under his belt, Thomas Menino has won his fifth term as Mayor of Boston, longer than any other mayor in Boston's history since it elected its first mayor nearly 200 years ago.  Menino became acting mayor on July 12, 1993 when he assumed the position after the resignation of Mayor Ray Flynn, who left to become Ambassador to the Holy See. Menino won his first election that November. On July 12 of this year, he became Boston's longest reigning mayor.
Menino defeated his opponents, the combined team of City Councilors At-Large Michael Flahtery and Sam Yoon, 57.3% to 42.4%. Menino addressed his supporters at the Fairmont Copley Plaza Hotel saying, "The headlines may read that today we were elected to a fifth, historic term. Let's be clear: We haven't made history with this election, but we will, with what we create of it."
—Tom Menino, Mayor of BostonAcross the city, at Venezia, an Italian restaurant in Dorchester, a somber Flahtery told the crowd, "Although the outcome of this election was not what any of us had hoped for, we have had some important conversations over the last year and we've also raised the expectations of Bostonians throughout every single neighborhood." He added, "We've given a voice to many people in this city who have not been heard for years."
Flahtery hoped to beat Menino using a unique tactic by adopting a running mate, fellow city councilor Sam Yoon, who placed third in the September primary election. Had Flahtery won, Yoon was to become deputy mayor, a position that was abolished after Mayor Kevin White left office in 1984.
Meanwhile, in Newton, Boston's western neighbor and the tenth-largest city in the state, voters elected it's first African-American mayor, Setti Warren, who is a former aide to Massachusetts Senator John Kerry. Warren is also an intelligence officer in the United States Navy Reserve who has served in Iraq. Warren defeated State Representative Ruth Balser by a vote of 11,210 to 10,747 in unofficial results. Warren will take over from the outgoing mayor, David Cohen.
To the north, in Lynn, the state's ninth largest city, a surprise upset occurred as City Councilor-At-Large Judith Flanagan Kennedy defeated incumbent Mayor Edward J. "Chip" Clancy, 49.94% to 49.78% by just 27 votes to become the city's first female mayor. A recount is expected in what has been a bitter mayoral race with plenty of twists including allegations of state election law violations by Clancy's campaign sending out fliers with her signature indicating a support for raising property taxes. 
On Kennedy's side, it was revealed that her campaign manager, Dennis Liberge, was convicted on drug charges 17 years ago in the state of Maine. Kennedy jumped into the race after the death of the previous challenger, former Mayor Pat McManus, winning the primary with a sticker campaign, winning by 211 votes.
On her victory Kennedy commented to the Boston Globe, "A win is a win. With a race this close, we're probably in recount territory. We will take 27 votes and see what happens."
Further north, in the city of Lawrence, the city elected it's first Hispanic-American mayor, State Representative  William Lantigua, who becomes the first Hispanic mayor in the state, with Lantigua beating City Councilor David Abdoo by just under a 1,000 votes.
To the south, in Quincy, a rematch occurred  between incumbent mayor Thomas Koch defeated former Mayor William Phelan, whom Koch ousted during the last election in 2007, by a unofficial margin of 54% to 46% for Phelan.
Massachusetts' second and third-largest cities also held elections. Worcester, the second-largest city in the state elected Joseph O'Brien to be the city's new mayor, defeating incumbent Konstantina Lukes. Meanwhile, Springfield, the state's third-largest city elected Mayor Domenic Sarno to a second term. They also voted to change mayoral term-limits from two-years to four-years. Sarno will serve a two-year term. 

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Tom Menino wins historic fifth term as Mayor of Boston; plus results from area cities