Despite its liberal reputation, the home of Jack Kennedy and Tip O'Neill has never elected a woman as governor or senator. And in Massachusetts Sen. Scott Brown's tight re-election race with Democratic challenger Elizabeth Warren, gender could prove the difference.
When Brown won his Senate seat in a special election in 2010, he came away unscathed by something his female opponent at the time would have had a much harder time explaining away. He posed nude for Cosmopolitan when he was 22 to help pay for law school.
About a year ago, Warren, who also went to law school and is now a Harvard Law professor, was asked how she financed her college education. She quipped: "I kept my clothes on!"
Days later, in an interview with Boston radio station WZLX, Brown had this response to Warren's comment: "Thank God."
That struck a nerve among women in the state.
They have seen Massachusetts consistently vote down women running for high political office. Neighboring New Hampshire is currently served by two women U.S. senators. Maine has two, as well. Connecticut has elected multiple women governors. But in Kennedy Country? Never.
Carol Hardy-Fanta of the University of Massachusetts says the state has an especially long tradition of politics as the path to wealth and influence.
"They say politics is a blood sport here and it is everywhere, I mean, everybody wants power but men are never going to give this up without a really big fight," she says.
Massachusetts is the lone state that tilted for dove George McGovern for president in 1972. It was the first state to legalize same-sex marriage. But Victoria Budson of Harvard's Kennedy School of Government says it's not as liberal as people might think.
"Massachusetts was founded by the Puritans," she says, "and some of that sense of Puritan propriety and norms and expected sets of behaviors has remained."
Warren has a shot at breaking some of those norms. In recent polls, she came out ahead of Brown among likely female voters. To try to chip away at that lead, Brown has been running several TV spots.
One declares that "Scott Brown is pro-choice, and he supports a women's right to choose." Other ads show him embracing his wife, who is a former TV reporter, or posing for the camera with his two daughters.
Some voters are uneasy watching gender play a role in the race. Boston retiree Mike Lloyd says stereotypes should not decide what could be a pivotal election nationally.
"It just doesn't influence me," he says. "I don't particularly care whether he's tall or handsome, or that she's not 25 and ravishingly beautiful."
Other voters, like Michelle Burrell, say gender does matter.
"Boston is full of majority men ... not ruling, but running the town. We need more women in the world putting a mark on this town," Burrell says.
Ten years ago, Shannon O'Brien lost the governor's race to a Republican man Mitt Romney. She says this year's tight Senate race may be different.
"I was outspent three-and-a-half to one," O'Brien notes. "Elizabeth Warren, I think, has leveled that playing field. This should bode well for her chances to win in November."
And where is that money coming from? Ironically, in her bid to become the first female U.S. senator from Massachusetts, Warren has raised much of her campaign donations from out of state.