He ran on the whole “I’m the guy you meet up with at the local bar after a long day of hard work” campaign. He was electable because he seemed relatable (I know he went to Yale and had a childhood we could only dream of, but to the average American at the time he was your neighbor, that was his campaign and it was genius).
The user can manually set the flag to whatever they want… Most people use the jolly Roger pirate flag if they’re gonna bother setting the flag though.