If I could play chess with anyone, it would be Josef Stalin. That would be something, to put it mildly.
If I wanted a cold, cerebral conversation about the “iron laws of history” while playing chess (or a cross-country road trip), I’d have to go with either Lenin or Mussolini, or maybe Franco in a pinch. Both are widely considered to have been exceptionally intelligent men (and they both spoke English, too!).
No endorsements implied - for discussion purposes only.
Too dangerous. Even if you lose and leave the game he may have someone stick an ice axe in your head. I think that's under the Trotsky Gambit in Modern Chess Openings.
How far we’ve fallen that you both felt compelled to qualify your statements.