I don’t know Ben Shapiro, but even if I were his best friend, I’m not sure I could tell if he believes what he says or not. I’m not sure if Shapiro himself knows. So this is purely speculative, based mainly on the statements you quote here.

It is possible to believe something is true and at the same time believe it isn’t true. People do this with professional wrestling or religious rituals (like the Eucharist).

My guess is that Shapiro makes these implausible statements about poor people because the poor represent what Jung would call his shadow side. Shapiro’s dominant side worked hard in law school (or cheated hard or whatever it took to graduate). His shadow side wanted to party and get drunk and sleep late. Shapiro’s shadow side thought that all that “work hard and you’ll succeed” was a pile of crap, because how can anyone equate success with material wealth.

Rather than confront or communicate with or (heaven forbid) try to reconcile with his shadow self, Shapiro’s dominant side lashed out at poor people, calling them stupid and undeserving, which of course enables his dominant side to say stupid things. He probably believes his stupid remarks because the alternative would be to question everything he has worked hard (or cheated hard) for in his life. He is afraid to know better.

Successful people who are in touch with their dark side know that “there but for the grace of God go they.” They are empathetic with the have-nots. They perform acts of charity, not because Nobodaddy in the Sky tells them they have to in order to get into heaven, but because they would want someone to lend them a hand if they were in that person’s shoes.

Shapiro may not (as you say) have a heart, but he has two minds, and they will always be at war.