It's hard to imagine Baker having the chutzpah, not to mention the power and resources, to pull such a stunt — as became clear four years later, when he bowed out rather than challenge Romney's lieutenant governor, Kerry Healey, in 2006.
The wait has paid off. This year, finally, is the perfect race for the man so long considered the perfect candidate. The 10 years he spent in private business, running the Harvard Pilgrim health-insurance giant, has inoculated him from Beacon Hill in a year when voters crave an outsider. His reputation as a wonky financial conservative fits the voters' concerns over looming state budget deficits, and serves as a perfect contrast to incumbent Deval Patrick, viewed by many as a weak leader, inadequate reformer, and tax-and-spend liberal.
His personal life has also lined up well for the run; his recent seven-figure salaries at Harvard Pilgrim make it easier for him to take a year and a half away from working, and his three daughters are now grown enough — the youngest is 13 — to ease the family strain of a marathon campaign.
Perhaps most important, according to political analysts across partisan lines, the election is there for the taking. Patrick is widely unpopular, with a majority of the electorate saying he does not deserve re-election. The only way he should be able to win, many have said from early on, is if the Republicans nominate someone who offends or worries middle-of-the-road voters.
Baker, who was uncontested in the GOP primary after Christy Mihos failed to garner enough support to make the ballot, seems to offer no such attack points for Patrick. Moderate, or even liberal on social issues, he doesn't scare off pro-choice or pro-gay-marriage voters. He is scandal-free, obviously smart and informed, and has succeeded at just about everything he's set out to do.
But all of this begs the question that insiders are repeatedly asking these days in private — and, increasingly, in the media: why isn't Baker winning? Why do most polls still have him trailing by at least a half-dozen percentage points with four weeks to go — prompting pollster Rasmussen to move the race from "Toss-up" to "Leans Democrat" last week?
It might just be that in all those years knowing that he could be governor, Baker didn't give enough thought to how to become governor. That doesn't seem entirely lost on the candidate himself. When I asked him Saturday what has been harder than expected about selling himself as a candidate, he replied: "Everything."
One of the things Baker has had to learn is the basic political art of working a room — something he says he's never done before. "Walking up to a room full of people you don't know and just walking up to people, and throwing your hand out and saying, 'Hey, I'm Charlie Baker and I'm running for governor' — it took me some at-bats to get me to the point where I could do that."
He needs to be good at it, because — despite his recent boast of "rock-star" response on the trail — people are not crossing those rooms to meet him. He was mostly ignored last Saturday walking through a crowded Needham Harvest Fair — in his former hometown — and had to approach people to make contact. His public events have been, for the most part, sparsely attended.