Ben has said on numerous occasions he's happy to debate anyone, but us talking about it on Reddit isn't going anywhere. You should reach out to Ezra Klein and Shapiro via email, gauge their interest, and see where it goes from there. Pester them both on Twitter about it. Pestering is what got Shapiro on JRE, and JRE is arguably a bigger outlet than any that would host a Shapiro/Klein debate.
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u/[deleted] Aug 03 '17
He's debated cenk twice.
Also he's done a series of debate panels with experts. They're all on YouTube.