Jason, I got this email earlier today from a savvy Democratic friend:
Watch out for this seat becoming a lot more competitive than it should and that's because of the dynamics of the election. It looks like Andy Card might be the only GOP candidate, at the same time there could be upwards of 20 Democrats with no runoff. Its conceivable that the Democratic nominee could be some no-name state assemblyman or Boston city council person who is able to get his/her people to the polls. The nominee could emerge with 9% of the vote. With small a margin we could be talking about a really eccentric nominee, one hardly ready for prime time. Card is making a pretty shrewd bet, and the quality of the Democratic nominee might completely cancel out being Bush's COS.
Seems possible. As a cub reporter for the Boston Phoenix back in 1998 I covered the race to fill Joe Kennedy's Boston-area House seat after he stepped down from that job. If memory serves there were about 10 candidates in the Democratic primary, which was won by Somerville Mayor Michael Capuano, who mobilized his city hall political machine to produce something like a 28 percent plurality. (I think turnout was about 25 percent, meaning Capuano was elected by about 7 percent of the district's eligible voters.) So, yes, strange things can happen.
That said, having served as Bush's chief of staff might come a close second to having played for the Yankees as a liability in the Bay State, even if Card was never a particularly villainous figure for the left--just a somewhat goofy one.