Recurring Guest Characters Andrew Weissmann 23 guest appearances Neal Katyal 15 guest appearances Rep. Jamie Raskin 11 guest appearances Rep. Dan Goldman 10 guest appearances Preet Bharara 8 guest appearances George Conway 8 guest appearances Sherrilyn Ifill 7 guest appearances James Carville 7 guest appearances Jim Messina 6 guest appearances Tim Miller 6 guest appearances Lisa Rubin 6 guest appearances Rep. Adam Schiff 6 guest appearances Claire McCaskill 6 guest appearances Guest Host 6 guest appearances Nancy Pelosi 5 guest appearances Jon Favreau 5 guest appearances Sen. Cory Booker 5 guest appearances Molly Jong-Fast 5 guest appearances Sen. Elizabeth Warren 5 guest appearances David Plouffe 4 guest appearances ⇤ « 1 2 3 4 5 6 7 8 9 10 » ⇥