In a new segment of the show, Eric and Kevin discuss within 20 minutes (that is part of the challenge) a favorite moment from history and, after the 20 minutes, some lessons that can be learned from it. 
Eric is second.  What could possibly have made the founding father, who was well known to be stoic and unemotional, a puddle of tears? Hint: a wound to the heart deeper than a bullet. 

Mount Vernon website
Rod Chernow - Alexander Hamilton