The 1990 Playboy interview also provides an insight into the meaning and the purpose of Trump’s supposed admiration for Putin. Trump saw little to admire in the Soviet Union:
I was very unimpressed. Their system is a disaster.
He showed no sign of being friendly with the enemy:
we should continue giving him [Gorbachev] credit, because he’s destroying the Soviet Union.
On the other hand, speaking, as I understand, of pre-Gorbachev Soviet leaders, Trump compared them favorably with US officials:
Generally, these guys are much tougher and smarter than our representatives. We have people in this country just as smart, but unfortunately, they’re not elected officials…
Trump was giving Soviet gerontocrats way too much credit – their system had always been dysfunctional and from the late 1970s onwards, the smell of rot was unmistakable. On the other hand, if the decline was systemic, not even the brightest and the toughest could stop it.
But what does toughness mean?
Tough is being mentally capable of winning battles against an opponent and doing it with a smile. Tough is winning systematically.
This explains a whole lot. If one ignores Putin’s domestic policies and only focuses on his foreign-policy record (I disagree completely with this approach but it comes naturally to some), one might concede that he’s been “winning systematically” as of late, unlike Obama.
Now as fifteen years ago, Trump is using the example of foreign authoritarians as a big stick to pummel his domestic opponents. A questionable method, but not entirely unjustified.