Massachusetts Gubernatorial Election, 2002 - General Election

General Election

O'Brien's campaign was hobbled by the short amount of time between the primary and general election, and by her having exhausted most of her funds by spending $4.5 million to win the nomination. She focused her attacks by portraying Romney as being out of place in Massachusetts. Romney had stumbled earlier in the year by not knowing that "MCAS" stood for the Massachusetts Comprehensive Assessment System of school exams. To soften his image of being rich and privileged and a wealthy corporate buyout specialist out of touch with the needs of regular people – an image that had damaged him in his 1994 U.S. Senate race – a series of "work days" had been staged over the summer, in which Romney performed blue-collar jobs such as herding cows and baling hay, unloading a fishing boat, and hauling garbage. Television ads highlighting the effort, as well as one portraying his family in gushing terms and showing him shirtless, received a poor public response. O'Brien now said in response that "Massachusetts doesn't need a governor who thinks getting in touch with working people is a costume party." She said Romney was "trying to mask a very conservative set of belief systems"; while saying she would not criticize his membership in the LDS Church, she attacked his substantial donations to Brigham Young University, objecting to their bar on expressions of homosexuality. O'Brien came out in support of same-sex marriage. Romney declared support for faith-based initiatives. Romney campaigned as a pro-choice candidate who would protect a woman's right to an abortion, and he rejected the endorsement of Massachusetts Citizens for Life, a pro-life organization.

Romney ran as a political outsider, just as he had in the 1994 U.S. Senate election, and as an agent of change, saying he would "clean up the mess on Beacon Hill." He said he was "not a partisan Republican" but rather a "moderate" with "progressive" views (although John W. Sears and several other state Republicans would later say Romney was from the more conservative side of the Massachusetts party).

Supporters of Romney hailed his business record, especially his success with the 2002 Olympics, as that of one who would be able to bring a new era of efficiency into Massachusetts politics. He proposed to reorganize the state government and stressed his ability to obtain federal funds for the state. Romney said he would cut $1 billion out the of $23 billion state budget by eliminating the usual suspects of waste, fraud, and mismanagement while still reducing taxes over a phased period. He also said he was generally against tax increases, but refused to rule out the possibility; he did attempt to paint O'Brien as a 'tax-and-spend liberal'. Romney contributed over $6 million to his own campaign during the election, a state record at the time. He raised nearly $10 million for his campaign overall. His campaign was the first to use microtargeting techniques, in which fine-grained groups of voters were reached with narrowly tailored messaging.

Jill Stein, internist at Simmons College Health Center and resident of Lexington, Massachusetts was the Green Party nominee for Governor. She campaigned against requiring that students pass the Massachusetts Comprehensive Assessment System tests to graduate high school, and in support of clean air and bilingual education. After being excluded from the first debate, Stein and Independent candidate Barbara Johnson sued the media organizers of the debate. Middlesex Superior Court Judge Linda Giles ruled against Stein and Johnson, stating that the state's campaign finance law do not apply to the press organizing political debates and that the invitations to Shannon O'Brien and Mitt Romney did not constitute a campaign contribution.

Carla Howell, a candidate for United States Senate in 2000 was the Libertarian Party's candidate for governor. Howell campaigned in favor of the ballot initiative that would abolish the state's income tax and reducing the size of government and against bilingual education.

Barbara C. Johnson ran as an independent candidate. Described as a "wild card, with ideas ranging across the political spectrum", Johnson campaigned against keeping MCAS as a requirement for graduation and in favor of giving abandoned housing to its tenants.

By mid-October, the backfiring television ads had contributed to Romney being behind O'Brien in polls. He rebounded with negative ads that accused O'Brien of being a failed watchdog for state pension fund losses in the stock market, specifically featuring a basset hound sleeping as bad men removed bags of money from the Massachusetts treasury, and that associated her husband, a former lobbyist, with the Enron scandal. Debates held instanced O'Brien attacking Romney repeatedly; he ended up referring to her style as "unbecoming", which engendered criticism that he was insensitive to women.

Jill Stein's impressive performance at the October 9 debate led to speculation that she could play a spoiler in the race by siphoning votes from O'Brien. In an effort to prevent losing votes Democratic to Stein, Arlington School Committee member Paul Schlichtman purchased the rights to jillstein.org and diverted the page to omitmitt.com, which stated that "A vote for Jill Stein just brings you four more years of Weld-Cellucci-Swift-Romney-Healey business as usual." Robert Reich delivered a similar message to Democratic activists, saying that "A vote for the Green Party is in effect a vote for the Republican Party". It was also speculated that Carla Howell's could also drain conservative support from Romney. However, none of the three minor candidates proved to be a numerical factor in the race.