In this video Chomsky debates a former Ford and Reagan administration official. Chomsky's performance is not unlike what he displayed in his debate with Richard Perle. What really makes him impressive is simply that he knows the facts and his opponents don't. They make false assertions. He gives the facts. They look stupid.
It's a pretty easy path to debate victory I suppose, and in my estimation it's usually true. The right wing just doesn't know the facts. Winning just means that you should know the facts and offer correction. People are often impressed, and maybe I think they shouldn't be. People have said as much to me. Wow, Jon, you know so much. You're so smart. That's what they say. I tell them it's not true. I don't think I'm particularly smart. I just think I've managed to step outside of what you might call a propaganda bubble and I've discovered some historical things. People know about Watergate. Few have heard of COINTELPRO. Many have heard about the Gulf of Tonkin incident. But most of them couldn't actually tell you when the US military began attacking Vietnam. If you know this basic stuff you'll find that your friends are often impressed.