The Most Unlikely American Presidents

The I'd say Alf Landon. He had the largest electoral loss of any candidate (well J.Q. Adams had a bigger loss in 1816...

Rufus King was the Federalist candidate in 1816. JQ Adams left the Federalists in 1808, and served an ambassador and negotiator under Madison. He was Monroe's Sec of State in 1817-1825.
 
How about Strom Thurmond?

No, I have no scenario for him being elected in 1948.

But he was President pro tem of the Senate in 2001, until Jeffords changed parties in June. Assume Gorton defeats Cantwell in Washington in 2000 (Cantwell won by 2,219 votes out of 2.4M). Then it doesn't matter if Jeffords changes parties, so he won't. In any case Thurmond remains as P.p.t. until the end of his term (3 January 2003).

Also assume the 9/11 attacks are postponed until New Years Day 2003, and that the attacks succeed in hitting the Capitol and the White House (instead of a miss and the Pentagon).

Bush, Cheney, and Speaker of the House Hastert are all killed. Thurmond becomes the first (and probably the only) 100-year-old President.
 
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