updated 9/17/2006 5:44:48 PM ET 2006-09-17T21:44:48

Despite its reputation as a liberal Democratic bastion, Massachusetts has not elected a Democratic governor since 1986. Democrats believe that’s all going to change this fall.

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Deval Patrick, a former Clinton administration official, leads polls heading into Tuesday’s statewide primary, although he faces a stout challenge from Chris Gabrieli, a Boston venture capitalist who has already spent $8 million in personal funds on his campaign.

Attorney General Tom Reilly, once the prohibitive favorite due to his law-and-order image and establishment support, has fallen to third in recent surveys.

Each of the Democrats has led Lt. Gov. Kerry Healey, a Republican hoping to become the state’s first woman elected governor, in hypothetical general election matchups. If Patrick wins the primary and a general election matchup against Healey, he would not only become the first black elected governor of Massachusetts, but only the second in the nation.

Yet some think Democrats are being too overconfident.

Republicans have held onto the Governor’s Office for so long by arguing they are a necessary counterbalance to the Democratically controlled Legislature.

The state’s current governor, Republican Mitt Romney, decided against seeking a second term and is exploring a 2008 presidential run. The last Democratic governor was Michael Dukakis, who left office in 1990, two years after his presidential campaign imploded along with the “Massachusetts Miracle.”

The ‘best chance,’ every four years
“Every four years since Dukakis left has been the ’best chance the Democrats have to win the governor’s race’ — until the Democrats lose,” said Mary Anne Marsh, a Democratic political consultant. “The Democrats also felt that way about beating George Bush — only to lose twice.”

Reilly, 64, started the year as the front-runner, but his image took a beating after he acknowledged calling a district attorney investigating the alcohol-related crash of the daughters of a campaign donor. Then the state legislator he chose to be his running mate quit after one day, following disclosure of unpaid taxes and student loans.

Patrick, 50, who headed the Justice Department’s civil rights division under President Clinton, shocked the field by not only winning convention-organizing caucuses in February, but also 58 percent of the vote — and his party’s endorsement — at the Democratic State Convention in June.

Gabrieli, 46, had been poised to become Reilly’s running mate before the attorney general passed over him to make his ill-fated selection of state Rep. Marie St. Fleur, D-Boston. In April, Gabrieli launched his own candidacy for governor. Since then, he has advertised virtually nonstop. His personal spending has already surpassed the record $6.3 million spent by Romney in 2002.

Issue No. 1: Income tax rates
The biggest issue of the campaign has been whether the state should roll back its income tax rate from 5.3 percent to 5 percent, as voters approved in 2000 but the Legislature ignored.

Patrick says no, believing it will trigger a hike in property taxes. Reilly says yes, to honor the will of the voters. Gabrieli has been pushing a plan to split future revenues so 40 percent go to a tax cut, 40 percent to new spending and 20 percent to the state’s rainy-day fund.

“Neither one of you get it. The debate is over. The people have voted,” Reilly said Thursday night to Gabrieli and Patrick, both millionaires. “You guys just don’t get what’s going on in normal people’s lives.”

Patrick retorted: “It seems to me leadership is being candid with people about the choices before us even when it is an unpopular choice.”

Gabrieli accused Patrick of being vague, saying: “You have been in the race a year and a half; got any specifics?”

The primary winner will face not only Healey, but also Christy Mihos, a convenience store magnate running as an independent, and Grace Ross, a member of the Green-Rainbow Party.

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