But was Reagan a hypocrite for not telling Gorbachev his country was evil to his face? You're arguing hypocrisy here
Yes he was.
Which is why the phrase "evil empire" was stupid as shit.
First of all, Gorby was not part of the "evil empire". He was a reformer of the soviet totalitarian system, and even the dim witted Reagan knew this. So I do not accept your premise.
That said, one always looks weak when they only have the bravado to say inflammatory shit in front of the safe harbor of a friendly audience, but won't use that word outside that comfort zone.
And if there is one things Russians can easily recognize, it is weakness.