Ben Shapiro is not a great debater in any sense. He's good at maintaining his calm, which to be fair is a great quality to have in debates, but he spouts absolute horseshit. He's incredibly condescending and he loves making the people he's debating angry, to make himself seem like the calm and rational one, like the time he kept referring to the trans-woman as a man. It was completely unnecessary, incredibly mean-spirited and completely expected from that virulent homo- and transphobic cnut. As someone else pointed out, he's also intellectually dishonest, disregarding any fact that contradicts his view, and often resorts to outright lies in order to try and get the upper hand. Then there's the fact that he frequently resorts to the Gish Gallop*, which is something a "great debater" shouldn't have to do.
Oh, and he spends most of his time debating college students and similarly inexperienced opponents, which helps create the impression that he's a master debater.
So yeah, it can be impressive to watch him eviscerate an opponent, IF you ignore or are unaware of all the dirty and cheap tricks he relies on to make himself look as if he's on top and in control.
*For the uninitiated, The Gish Gallop is a debating technique that involves flooding your opponent in so many arguments, usually weak ones, that they will be unable to offer up a proper counter without great effort, resulting in them appearing stumped or flustered, which in turn makes it seem like you have the upper hand.
Saw a couple naming Jordan Peterson as a better debater. He's just as intellectually dishonest as Ben Shapiro, and spouts equal amounts of shit (and is an equally transphobic cnut). Like Shapiro, the only thing he's actually good at is staying calm and using cheap tricks to make it seem like he's winning. Managing to make your opponent angry, while staying calm yourself, or spouting so much horseshit that your opponent has no hope in hell of refuting even a portion of it, is not winning a debate.
My wish is for anyone debating them, when they start to try and control the discussion through their normal means, to go "Sorry, it's impossible to have a discussion with you if you're not going to stick to facts. I'm out." Instead, people try to take them on, get understandably provoked by the shit they pull, and thus play right into their hands, resulting in another YouTube clip of Jordan or Ben "destroying" someone.