I did not understand it that way. Putin is probably smarter than Trump (though he does not deserve to be regarded as a mastermind IMHO). The parallel I find interesting is that both are authoritarians who were helped to power by billionaires who thought it would serve their interests. We know the fate Russian “oligarchs” later met.
Russians close to power have historically often met that fate - at least since 1917, I suspect either prison or forced internal or external exile was more common before that. Americans not so much I think, so this probably won't transfer.
No, one is a cruel fox and another one is a stupid monkey.
Their skills lie mainly in adaptability to the situations they found themselves in and using them, but neither is a mastermind.