In this episode, John Jay walks right into the Anti-Federalists’ critique after once again overselling a historical reference. This time it’s the Scottish union to England. The Anti-Federalists respond on behalf of the proverbial “common man”. Can Jay handle their populist arguments? Jay warns of America’s decent into another version of Europe, and argues how the powers of Europe at the time would have preferred a fractured America. He believes the Articles of Confederation sets America up for failure, while the Anti-Federalists claim “user error”. The Anti-Federalists focus on diffusing power back to the people. Cary points out that if Jay had time travel, he could have borrowed Justice Oliver Wendell Holmes’ Bad-Man Theory to shut the Anti-Federalists down. In the end, Jay earns a well deserved respite from Justin and Cary’s continuous attacks.