Writing for Politico, Blake Hounshell asks why President Trump admires Vladimir Putin, and for that matter Kim Jong Un. I have an insight why this might be true, one the author doesn't mention.
Both those autocratic leaders manage to play "above their pay grade." They cleverly exploit whatever advantages their relatively poor lands possess.
Kenny Rogers sang that "every hand's a winner and every hand's a loser." A good poker player can bluff with a poor hand and, at least sometimes, win.
I suspect Trump sees these men as clever players doing relatively well with what are basically poor hands. They lead poor countries with far more problems than answers, and manage to make them at least somewhat powerful. Like them or hate them, they show a real skill.