Trump’s eventful weekend of golfing, sightseeing, and ignoring the imploding effects of the war in Iran has Jon Stewart wondering who the hell the president has been claiming to negotiate with overseas, and whether this "top person" even exists. Plus, airport chaos amid a government shutdown has ICE filling in for the TSA as part of Trump's escalating chaos rampage. Jake Sullivan, former National Security Advisor, Harvard Kennedy School professor, and co-host of “The Long Game” podcast, joins Jon Stewart to break down the war in Iran, U.S. foreign policy, and the future of nuclear negotiations. Sullivan shares his insights on President Trump’s approach to Iran and Iran’s “coherent and clear” strategy. Plus, Sullivan reflects on his time working on secret negotiations with Iranian officials during the Obama administration and tells the story of a historic first direct contact between U.S. and Iranian presidents since 1979.