The hosts unravel the lives and legacies of two rulers of Russia, Joseph Stalin and Vladimir Putin.

The hosts discuss Stalin's bizarre childhood, his outmaneuvering of Trotsky, his superb use of propaganda, the great purge of suspected dissidents, how agricultural collectivization lead to famine, his leadership during World War 2 and his eventual death. 

They also discuss Putin's early life as a KGB agent, his rise to power within the Russian Federation, his capitalization on the Chechen war, control of the media, murder of dissenters, meddling in US elections, the Syrian civil war and invasion of Ukraine.

These two dictators battle it out in Round 13 of the knock-out tournament to determine the single greatest dictator of all time. One of these two dictators will be eliminated from the tournament and the other will remain in contention to be crowned history's biggest dictator.