So in this timeline, Mitt Romney wins the United States Senate Election in Massachusetts of 1994, unseating incumbent Senator Ted Kennedy. Romney narrowly wins re-election in 2000, but at the same time, Vice President Al Gore wins one of the close states he lost in OTL, thus winning the electoral vote and the Presidency. As OTL, Romney is elected Governor of Massachusetts in 2002. Come 2004, Governor Romney decides it is the ample opportunity for him to challenge incumbent President Gore. I could imagine Romney winning GOP Establishment support in the Republican Party Presidential Primaries of 2004 (or contending closely with Jeb Bush for it), but do you think he could win the nomination or is it Senator John McCain of Arizona's to lose? Who do you think Romney's theoretical Vice President would be? Who do you think Romney's Democratic opponent in 2008 would be and do you think he could be them?
 
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1994 was not close in Massachusetts--EMK defeated Romney by better than seventeen percentage points. https://en.wikipedia.org/wiki/United_States_Senate_election_in_Massachusetts,_1994 Even if by some miracle, Romney should win, he would have such a liberal record as senator (if he hoped to win re-election in 2000) that it would make it impossible for him to get the GOP presidential nomination. (He could make a fairly conservative record as governor after 2002 because he didn't run for re-election in 2006. Moreover, the "liberal" positions he did take were on *state* issues like Romneycare--which conservatives didn't like but could live with, because he didn't come out for *national* compulsory health insurance. In the Senate, by contrast, either Romney would have to take liberal stands on national issues or he is not going to get re-elected, narrowly or otherwise, in 2000, a year when George W. Bush got *32.5 percent* of the vote in Massachusetts. https://en.wikipedia.org/wiki/United_States_presidential_election_in_Massachusetts,_2000)
 
1994 was not close in Massachusetts--EMK defeated Romney by better than seventeen percentage points. https://en.wikipedia.org/wiki/United_States_Senate_election_in_Massachusetts,_1994 Even if by some miracle, Romney should win, he would have such a liberal record as senator (if he hoped to win re-election in 2000) that it would make it impossible for him to get the GOP presidential nomination. (He could make a fairly conservative record as governor after 2002 because he didn't run for re-election in 2006. Moreover, the "liberal" positions he did take were on *state* issues like Romneycare--which conservatives didn't like but could live with, because he didn't come out for *national* compulsory health insurance. In the Senate, by contrast, either Romney would have to take liberal stands on national issues or he is not going to get re-elected, narrowly or otherwise, in 2000, a year when George W. Bush got *32.5 percent* of the vote in Massachusetts. https://en.wikipedia.org/wiki/United_States_presidential_election_in_Massachusetts,_2000)

While I agree that it's very, very unlikely for Romney to unseat Ted Kennedy, it's not impossible. Probably not on his own, but if Kennedy had a health scare (heart attack, early warning signs of cancer, something), it's possible. On top of that, a Gore win in 2000 totally changes the game for the GOP. They won't be nearly as ideologically driven in this alternate 2004, and I could see a center-right, technocratic Romney making an appealing candidate. A Gore squeaker wouldn't utterly discredit Bush's "compassionate conservatism", and I could see there being an opening for Romney.
 
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