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So this thread got me thinking:
https://www.alternatehistory.com/discussion/showthread.php?t=191638
Create a TR/FDR ticket for any party you deem most plausible and in any election you deem most likely.
Not sure it could work, but that's why it's a challenge. Not sure Roosevelt vs. Roosevelt is possible either but it got some good responses.
Bonus points awarded, of course, if TR/FDR wins.
Go.
(They can also remain in differing respective political parties but the ticket has to be, obviously, for one party.)