Ben Shapiro certainly annoys me. He's basically popular because he can own libs from time to time. Once again, it all comes down to liberal tears. I used to do national level debate when I was in high school, and I've argued with a million guys like Ben: fast talkers, who kind of blanket you in sea of obfuscation and mitigation... leaving you exhausted, and in the end, you have to admit he makes it hard to argue with him.
But like a lot of them, it's only mitigation, or it's switching ground to favorable points, or it's false equivalencies, or it's correlation equalling causation... an encyclopedia of disingenuous forms of argumentation. Ben's whole argument usually rests on the idea that most of us will be too lazy to actually research his points, and disprove them wrong. And he's mostly right. It's not worth my time and effort. If someone were to call him out on something, he'd just go somewhere else to rationalize and defend himself... leading to more branches of things that need to be disproven... to infinity.
As a person, I find him pretty darn smarmy. He seems like a real tool, to me.. to be honest.