Returning to the question: Which US President are you most closely connected to? I'd have to say, in all probability, James Madison. Judge Edmund Pendleton is a great, great, etc., uncle of mine (on both sides of my family [it happens]), and he was a cousin of James Madison (i.e. I must be, too.). I won't go into the details because there are probable misattributions in the Wikitree pedigree, suffice it to say, the relationship finder makes us out to be cousins as well.