I doubt even Sowell would convince Castro and Chavez' old buddy Galloway of the wonders of capitalism.
Anyway, it doesn't seem to be Sowell's style to do comedyish podcasts, he'll usually just go to promote his books with old friends at the National Review or the Hoover Institution or something. Same with Richard Epstein or whoever it might be among Libertarian economists or quasi-economists. Regarding foreign policy, Dore might get some old paleocons from The American Conservative on, perhaps even Pat Buchanan himself. He's usually a good sport, and surprisingly tolerant of naughty language and such, for an old super social conservative.
Ive probably been the poster with most number of heated discussions in this board over the years.... and I can assure you I won at least 90% of them.
dhobi ka kutta, na ghar ka na ghat ka