It’s kind of odd but I stumbled upon something rather strange that would have happened had the GOP won the election in 1940.
Charles McNary would have been VP and, assuming nothing else changed, would have died in February, 1944 leaving the office of Vice President vacant.
Wendell Willkie would have been President and, assuming nothing else changed, would have died in October, 1944 leaving the offices of President AND Vice President vacant.
This would have created as scenario in the middle of the biggest war in history where Congress would have had to elect a president under the 20th Amendment.
That is a fascinating possibility, but isn't it likely that the VP would have been replaced between February and October?