Massachusetts, home of the Kennedy dynasty, the first state to grant marriage licenses to same-sex couples, and the only one to vote for George McGovern for president in 1972, revels in its über-liberal reputation. And while Democrats hold most of the elected offices that matter, the paradox is that voters here don’t seem comfortable electing women to statewide office.

Massachusetts has never elected a woman to be a U.S. senator or governor, unlike North and South Carolina, Oklahoma, Louisiana, Kansas, Texas—and Arizona, which has elected women from both parties as governor. All are considered far more conservative than the Bay State. Closer to home, New Hampshire and Maine both have two women senators—only one of whom is a Democrat. Vermont and Connecticut have had female governors, too, including Ella Grasso, who in 1974 was elected governor of Connecticut and became the first woman in the country to serve as a governor who did not succeed her husband.

The expected 2012 showdown between Republican Sen. Scott Brown—who last year unexpectedly seized the Senate seat held by Ted Kennedy for nearly a half century—and consumer advocate and Harvard law professor Elizabeth Warren will test anew the state’s track record on women politicians.

Massachusetts has long considered politics its favorite pastime after the Red Sox. The three previous speakers of the state House, all men, have been indicted, with one pleading guilty to tax evasion and another convicted on seven federal corruption charges. This is the big league, and politics is a blood sport here, a tradition going back hundreds of years. First the Brahmins held on tightly to power, and then the Irish Catholics fought their way in.

The state has launched national leaders from President John F. Kennedy to U.S. House Speaker Tip O’Neill, and presidential candidates Michael Dukakis, John Kerry, and now Mitt Romney—who, if he is the GOP nominee, probably won’t carry the state he governed only five years ago.

“Men want it bad in Massachusetts. They want to be in power. Getting elected to statewide office here is a big launching pad for national politics. The men don’t want to give that up. Men see the opportunities and are damned if they’re going to let women in,” says Carol Hardy-Fanta, director of the Center for Women in Politics & Public Policy at the University of Massachusetts at Boston.

In its entire history, only four women have represented Massachusetts in Congress. The first was Edith Nourse Rogers, a progressive Republican who succeeded her husband and served from 1925 to 1960, becoming the nation’s longest-serving congresswoman, a record that still stands. Republican Margaret Heckler served in the U.S. House from 1967 to 1983, after which there was a gap of almost a quarter century until Niki Tsongas became the next woman elected in 2007. She represents the state’s Fifth District, the same seat held by Rogers, and by Tsongas’s late husband, Paul, before his election to the Senate, his run for the presidency in 1992, and his death from non-Hodgkin’s lymphoma in 1997.

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