Is he trying to play both sides?

“Yes, Cuba and Venezuela are run by evil commie dictators that need to be taken down but our embargo on Cuba is bad.”

I think it's the old "liberal pacifism" shtick. "The oppressor is bad, but the resistance forces using violence to resist the oppressor are also somehow bad because they use violence."

No amount of softly condemning the USA’s deplorable actions right after tearing into AES countries is going to change people’s minds.

Exactly. It confuses the issue and puts the oppressed in a position where they are only ever allowed to be a victim, never a self-determining group who is capable of defending themselves.