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From the "Alternate Wikipedia Infoboxes" thread:

The Absolute Worst case Scenario for the Republicans:

No, it's saying he was a Republican before the election! Apparently, he got thrown out of the Democratic party last year because he'd disappointed so many of them? But, apparently, he made his way back.

Maybe it's from a timeline where he was elected as a Republican, but then defected to the Democrats for 2012.

Hmm. If he's always been a Republican, then if we want his background to be the same, we'd need the Chicago political machine to be Republican. (Note that the infobox still places him from Illinois.) That'd change so much that I think it'd butterfly away at least half our modern politicians.

Another idea I had is that he gets his start in local Chicago politics, as a reformer - a Republican who cleans up the machine. That would give him a lot more substantiation for his message of "change"; I'm pretty sure he could make the jump directly from mayor of Chicago to President.

Lots of bonus points if you can do it without changing the Reagan Revolution or dramatically reducing its support in the Republican Party.

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