New York Post John Podhoretz columnist makes an interesting point on Morning Joe about why American Presidents tend to like working with dictators (Trump is not entirely alone).
When a President ask a dictator for a favor, the dictator can deliver on that favor right away. When the President asks a democratically elected leader for a favor, the leader will have to hedge, poll their various constituencies, and take the pulse of their nation before the leader can respond, And even then, if sentiment changes, the democratic leader may may not be able to deliver on a requested favor. The ability of dictators to reliably deliver on favors makes them an easy ally that Presidents find hard to resist.
John Podhoretz comments starts at about the 13:48 mark.