I'm afraid I couldn't get past more than twenty minutes and ten seconds...
I like Ben Shapiro and he's a highly intelligent person, but even by his own admission - and an average Orthodox Jew would tell you the same thing - he's not a talmid chacham (rabbinical scholar, whether ordained or not). I don't know on what sources he's basing his views. It's kind of impossible to have a proper Jewish theological discussion around his views if he doesn't say from where his views come
from.
This Rapaport dude, though? "Not a token Jew"? Yeah, right. He thinks he was a practicing Jew because his family coasted from Orthodoxy all the way to Reform and because he had a Bar Mitzvah and because he studied in Hebrew School as a kid and hated every moment of it (hence leaving ASAP). What does that make him? In my opinion, a Jew with poor Jewish education. Perhaps better than nothing, but I would say that he is, in fact, a token Jew. In other words, not really qualified for much of anything when talking Judaism, but "yay, he became a Christian, we got another one, folks!"

Another what? That's right. Another Jew who knew next to nothing about Judaism and clearly disliked it and was somehow ensnared into Christianity. Kudos, folks.