He had a debate with Cenk Uygur and they both basically ignored the strongest point of the other but, that aside, he did well rather than either just talking past each other or either of them being embarrassed. He also had a debate/conversation with Piers Morgan that was amusing in that Morgan basically refused to acknowledge that they had any common ground. Most punditry is just preaching to the choir but I think Ben has both pretty reasonable arguments speaking on his own and debating others, I don't see how he's afraid to debate people with other views or against those who could be considered more advanced.
IMO, Ben Shapiro is a joke. He presents himself well until one dissects his arguments. 9 times out of 10... he'll start with an obvious fact... he'll say something like, "see, that's obvious, we all agree with that." Then, rather hastily, he'll derive a maxim from that observation that isn't true at all, but he uses it as an extension of his original observation. "Well, x = y, and we all agree that x = y... so, it's obvious that y=x-z.. that's clear." When it's really not clear at all. For instance, on the Joe Rogan show, he was asked point blank.. what do you have against same sex marriage? His answer was, "The issue is not whether I care about two gay guys getting married. This issue is whether I prefer traditional marriage." See... that's a cute line... but what the flip does it actually mean? If he prefers "traditional" marriage over "non-traditional marriage"... then clearly, he cares. Ben is a funny guy who likes to spin cute little arguments that fall apart when actually analyzing them.
The other half of the time, he's putting deliberate red meat out there... solely to criticize liberals in the culture wars. He's gotta do that.. that's where his dollars come from. At the end of the day, the most important thing to red hats are those sweet, sweet liberal tears.
Ben is TOTALLY preaching to the choir. His audience is solely composed of conservatives. That's his whole appeal... that he pwns *******s. But outside of his echo chamber when he can't control the situations and is actually subjected to cross examination.. I've never been impressed personally. I used to debate in high school, and I've seen a million guys like Ben. Someone who says stupid stuff really well. It's paper thin.