He excels at what I guess you could call debate set pieces. Most of his mic drop and viral LIBTARD DESTROYED BY LOGIC moments seem to come about from him being allowed to frame up the discussion/debate/whatever on his terms. Lots of "let's say... " or "let's suppose... " and whoever's trying to debate him winds up led along by the nose and trapped because they're intimidated or unaware of what's happening.
Having each one of his "debates" be like a singular isolated skirmish is also helpful to him because he contradicts the ever-loving hell out of himself constantly. It frees him of the need to have a coherent worldview. If you pay attention to him long enough you'll see that there's little continuity in the poo he says other than accusing anyone who looks at Israel the wrong way of being a bigot, his various attacks on LGBT people, vague admiration of "the west", etc. Earlier this month for example he was calling out those boycotting the Trump stationary bike guy on Twitter. This led to him getting ratioed as everyone pointed out the many, many times Shapiro himself called for boycotts against a bunch of different companies for their political stances, whether real or implied. Like Ritz crackers because they advertised on Al Sharpton's old TV show, how he was canceling his SI subscription because some ess jay dubya stuff rustled his jimmies, etc. He was tying himself in knots arguing how that's totally not the same thing as boycotting a company because of their politics, somehow.
The aforementioned Andrew Neil thing is another good example. Shapiro did not see that coming, he was not prepared for somebody to cite stuff he's actually said and ask him to explain it point blank. He turned into a hyperventilating mess and accused the guy of being a leftist lmao.