He also took the risky step of attacking O'Brien face-to-face in their debates. As feared, Romney came across to many voters as patronizing and mean — but O'Brien's defensive errors proved more damaging.
The lesson seems to have stuck with Romney in the 10 years since that election — most of which he has spent seeking the presidency.
In that time, he has spent tens of millions of dollars on ads and messaging, almost all of it on so-called "comparison" ads deriding his opponents, from Rudy Giuliani to Barack Obama. His campaign has barely even tried to persuade voters to like, respect, or admire the candidate himself — or even get to know him.
This suggests that Romney has data showing that national audiences are no more open to liking him than Massachusetts residents were.
The negative image of Romney is so pervasive, it's easy to forget how counterintuitive it is. On paper, at least, candidate Romney should be an easy sell.
Few people have as perfect a life story as Romney. He has attended the right schools (Stanford, Brigham Young, Harvard), worked at the right firms (Boston Consulting, Bain), and done the right selfless public service (Olympics, governor). He has had stunning successes, without notable failures (except his 1994 US Senate loss to Ted Kennedy). He has a perfect family, anchored by a 43-year marriage. He is a devoted religious adherent who has served his church and community.
None of this has ever resonated with the public. That may be, as some contend, because he cannot overcome negative attitudes toward business executives. (It has often been said that Romney reminds people of the CEO who once fired them.) Others blame anti-Mormon attitudes.
Another popular theory holds that Romney is not relatable because he has never faced tough times or hard setbacks. In several key speeches, including his campaign kickoff in June 2011, Romney has awkwardly resorted to telling the against-the-odds rags-to-riches story of his father.
There is probably some truth to all of those factors. But there's also something more basic: his personality simply fails to translate from the personal to the public.
It's tempting to think that Romney just doesn't have a winning personality — that he is one of those wealthy, powerful men who misinterpret others' obsequious toadying as proof of his popularity.
But conversations with people who have known him over the years have convinced me that Romney really is easy to like, when he is off-stage and just being himself.
"He has a great sense of humor," says Charlie Baker, 2010 gubernatorial candidate in Massachusetts, who has helped on past Romney campaigns. "He's very self-deprecating, too. I expect they'll find a way to show that off [at the convention]."
They can try. And Baker may be right when he says that professional politicos overstate the extent to which casual-attention voters have formed strong opinions at this stage of the campaign.
Still, there's precious little evidence that Romney has found any way to make people like him, which makes it very unlikely he'll discover one now.
We're also a long way from the days when Americans were more or less force-fed the conventions, which the broadcast networks covered live for hours each night.