Shapiro is a bad faith debater. He has openly admitted to it. He debates liberals and uses bad faith arguments to trip people up. He built his career on this, saying outrageous, racist, sexist, etc things...and now that right wing Nazis are running around he's trying to act like he had nothing to do with this because he's Jewish (and they hate him too). Go back and read some of the stuff he was writing during the Obama years. Hell, read some of the things he said about Obama.
The only way to engage him is to ignore the obvious bad faith nonsense. He did an interview with Andrew Yang a couple months ago that was actually good. You could see Yang dodging the bullshyt and focusing on facts, and he managed to intrigue Shapiro enough that they had an actual conversation/debate.