Ben is a seasoned debater who comes prepared to engagements and has made his fame in making "the man on the street" look stupid.
Your typical person person on the street is going to engage in logical fallacies, they won't be quick with responses and very likely didn't prepare for a back and fourth and their decision to engage with Ben was likely driven by emotion. Their political slant or the issues are irrelevant. Ben eschews confidence and picks people like this apart and will expose problems with their arguments and fires off like a machine gun without missing a beat. However, the problem is, the people he embarrasses having flawed arguments and not being informed and prepared to engage, does not mean Ben is right.
I think that is the problem I think people fall into with Shapiro. They see videos of him destroying some dumbass ill informed, ill prepared college kids and think he's some powerhouse intellectual and every position he holds must be right or else he wouldn't be owning all these libs.
It's no different than when Comedy Central sends a guy to conservative boomer rallies and just give them the basketball and let them dunk on themselves.
In both cases individuals are being exposed as idiots. Those people being clueless mouth breathers has zero impact on the veracity of opposing positions of the issues at hand.