I remember following Harold Ford's senate race in Tennessee back in '06, and i distinctly remember being completely unable to tell the difference between his platform and a republican's. So I can't say i was terribly unhappy when his was the one tossup seat we didn't win.
But what I don't remember is him being stupid.
If Harold Ford isn't stupid, he should know that a "carpetbagging" conservative from Tennessee will never win the overwhelmingly liberal New York primary, no matter how much money he spends. But now that I think about it, he'd fit right in with the "moderate" republican party of New York, wouldn't he?
And considering that all the pundits say that 2010 is going to be a republican year, and with Rudy Giuliani bowing out of the race, he'd might think he'd have better luck running against Gillibrand as a Republican than as a Democrat.