Mitt Romney never won the Massachusetts senate seat though he did win the governorship of Massachusetts in 2003. Mitt did however run against Ted in 1994 for the seat and put up quite the fight but in the end Ted proved to be the clear winner getting re-elected 58% to Mitt Romney’s 41%. If you’re talking about the Republican Scott Brown who won the seat in 2010 then yeah, I too am surprised MA elected him as was the nation but now it’s once again in the hands of a Democrat.