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Yes, this is exactly what it sounds like -- with a PoD no earlier than 1866, how much can the life of Theodore Roosevelt be made to resemble that of fictional character Bruce Wayne, up to and including dressing up as a bat at night and fighting crime in a large city (likely New York)? Bonus points if he's still becomes President of the United States.
And before anyone else says it -- yes, this may very well belong in ASB, but seeing as it technically didn't involve science fiction or magic, I figured I'd give it a go here first. No offense to the board meant.