He’s not trying to do gotcha moments. He’s challenging the way liberals think about many different issues. Liberals aren’t used to others pushing back on their opinions and will usually walk away when challenged on their worldview.
It's not as much that Charlie is a great debater, as it is that he KNOWS THE FACTS AND TRUTHS and the ones who confront him mostly are filled with lies, false hate and hoaxes. Doesn't matter if those who opposed were greater debaters, they support lies, racism and a lot of evil.
The gotcha guy is ignorant and his words have been debunked 100's and 100's of times over. He is basically an uninformed fool who has soooo much to learn about life. But he will work hard to hold on to his misconceptions and prejudices.