So far most speculation of this whole thing from the perspective of Chomsky being such an intellectual that he just can't stop himself from having interesting debate and stimulating conversation even if that happens to be with monsters of facilitated by monsters.

There is however another more negative angle to analyse this from. You could also argue that Chomsky knew what his role in capitalism was, deeply so, more than most people on the planet. I find it somewhat difficult to imagine that Chomsky did not know that he was elevated to stardom by capital, given interviews and exposure and much much more because he was a palatable far-left, an unthreatening far-left, a figure of the left that represents no danger.

If Chomsky knew this, you could also argue that he knew he is a component of capitalism reinforcing capitalism by acting as the furthest left people would reasonably go, and also by publicly saying negative things to anything further left than he was. He thus acted as a prevention of people moving further left. If Chomsky knew this, then he was a willing participant in reinforcing capitalism, and knew his role very well.

If you take this route of analysing the situation, you could draw the conclusion that his friendship with Epstein and "fantasising about the caribbean island" are actually him taking part in the rewards of taking on that role within capitalism, quite knowingly.

This is the most cynical view to take of it, but one that I don't think should be ignored. Given Chomsky's works I find it difficult to believe he never considered his role, he must have had some self awareness.