Man this is some top-shelf shithousery by annie. It's fun to break down his method:
He plays a game. He gives you a long anecdote and in that anecdote, he's very clearly making an argument. It's not a complicated argument, you can follow it, it's pretty explicit. Then, next to the anecdote, he includes a conclusion. So it looks like [Long story about how America supported post cold war RU via the IMF] / [conclusion: America is directly responsible for putin's power and his aggression]. Now, any logical person makes a leap and says, "Okay, but America didn't start this war and has stayed uninvolved....why does that apply?". He comes back and says, "I never said that America caused this war, you cannot read, you didn't understand, you're stupid". Obviously not in that language. So he's constantly constructing what he's saying in this very slippery way that anyone engaging with his ideas on his terms is going to naturally draw conclusions about how he's getting to his ideas, but the way he constructs them isn't an argument with evidence, it's very loosey-goosey and so he can constantly call you out on misrepresenting his point and claim he never said the thing you are attributing to him, etc.
So what results are these "debates" or confrontations where people try to talk to him or engage him about his ideas in a critical way and he can shut them all down, which is fun for some people. It's a display of intellectual superiority for some, and a frustrating and puzzling experience for his opponents because he'll immediately backtrack on anything you try to pin him down on. So it produces....great content! It produces a lot of videos where some fumbling liberal/leftist is trying to engage with what he said and he stomps all over them by claiming they don't get it and that's some gooooood youtube. Ben Shapiro and Crowder do the same schitck, and if you don't know that you're going into that scenario when you talk to them, you'll lose just based on the rhetorical stratgies. They look smart and cool without even really talking about the ideas, because the POINT is not to talk about the ideas.