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2016 is probably the best year for Cain, since it's a good year for Republicans overall, while the GOP is radicalized enough to go for a figure like Cain- it depends on how crowded the field is ATL.
In a President Kerry or President Gore TL, the Dems are likely to lose in 2004/2008 due to incumbency fatigue. After 12+ years in the wilderness, the GOP might be suspetible to an outsider candidate like Cain.
I think getting Cain to win the general election is easy if he runs in the right year, the question is how he's in a strong enough position to win the nomination.
Good point Ulysses! But Trump has not(yet)
been caught fooling around on his CURRENT
wife; Cain was. Furthermore, I'm pretty
sure that last year IOTL he did not
receive a majority of the primary votes
cast. He also had the luck of running against
a slate of quite unappealing candidates,
whereas in 2012 Mitt was the G.O.P.
flavor of the month. Some Republicans
turned to Cain anyway but I think that many
of these voters were looking for the 1st
excuse to come along to ditch old Herman-
which in the end they did. Finally, Trump
seems to be the exception to all the rules!