But Romney got back on track by slamming O'Brien with a barrage of TV ads depicting her as a lazy basset hound "watchdog" who dozed while suited men piled bags of stolen state money into a truck emblazoned with the "Enron" label. The ads cited the state's billions of dollars in pension fund losses, including $23 million in stock from the Houston-based energy company that collapsed in 2001. O'Brien's husband had been a lobbyist for Enron.
O'Brien said the image was unfair and inaccurate. "But when you spend a lot of money on ads like that, it was effective," she said.
The attacks drove the race back onto Romney's outsider theme in the final weeks of the campaign, helping him win over independent voters, who dominate Massachusetts elections.
"During those last three weeks, Mitt really took the gloves off," Coes said. "He put aside efforts to be likable. He was disciplined and tight and tough."
O'Brien countered by going after Romney's business background. Romney amassed a fortune, now estimated to be as much as $250 million, by helping found the venture capital firm Bain Capital. Her ads cited Bain's role in laying off workers in businesses it took over, but the spots never gained much traction.
O'Brien said Romney did a good job selling himself as the turnaround guy, the successful businessman who saved the Olympics. She recalled one TV reporter asking her what it felt like to run against an "icon."
Romney also avoided the Republican label, pitching himself in the heavily Democratic state as a successful businessman capable of solving its fiscal woes. His moderate tack was a nod to demographics. Democrats outnumber Republicans by about 3-to-1 in Massachusetts and roughly half of voters are independent.
"I think people recognize that I'm not a partisan Republican, that I'm someone who is moderate, and that my views are progressive," Romney told New England Cable News in 2002.
His political success that year was forged in hard-won lessons from his first foray into politics, a 17-point loss in 1994 to Sen. Edward M. Kennedy.
Many thought Kennedy would be vulnerable given his hard-partying image and the 1991 Palm Beach, Fla., rape case against his nephew, William Kennedy Smith. Smith was acquitted, but Kennedy testified about taking his nephew and son Patrick for drinks at the bar where Smith met his accuser.
Romney hit Kennedy as a big-government liberal and avoided personal attacks.
But Romney's candidacy withered under a barrage of attack ads that cast him as a greedy venture capitalist whose firm cut jobs and slashed salaries at companies it took over. Angry workers from an Indiana plant even trekked to Massachusetts to dog Romney, who never quite recovered from the negative onslaught.
Kennedy outspent Romney, pouring much of his money into attack ads.
"For Romney, it was a costly learning experience, but it was a learning experience," said Tad Devine, a senior Kennedy adviser.
Romney made sure he had the money advantage in 2002. He raised $9.4 million, including some $6.3 million from his own pocket, and spent much of it on attack ads. O'Brien spent about $6.2 million on her campaign.
"Kennedy pounded him pretty good with the attack ads, and Mitt learned: Do it early, spend as much money as you can and keep it up for as long as you can," said O'Brien.
- Watch live at the Democratic National Convention
- Germany: Syrian asylum seekers blows himself...
- Verizon buys Yahoo for $4.83B, marking end of...
- Gunfire at teen nightclub party leaves 2...
- Trump taunts claims that Russia hacked DNC...
- Dems' division, emails roil party on Day 1 of...
- Athletes using sports platforms to push for...
- Germany: IS claims responsibility for attack...
- If Mitt Romney endorsed Gary Johnson,... 66
- Hillary Clinton promises steady hand in... 54
- Sarah Silverman: Bernie-or-bust Dems... 49
- Is Bernie Sanders an atheist? 44
- Trump says Russia should find Clinton's... 43
- Obama boosts Clinton: Carry her like... 41
- Clinton wins historic nomination,... 37
- After turmoil, Sanders, Michelle Obama,... 31