If you are new to the Reality Winner story, this is an excellent place to begin. There are a number of things I disagree with in this podcast, especially the assumptions and analysis of Chris Hayes at certain points, but it is well worth listen to.
If you only have time to listen to one podcast, I would suggest The Majority Report. Sam Seder consistently chooses material that is challenging and different from anything you will hear on the corporate media.
Sam hosts USC Law Professor Jody Armour (@niggatheory) to discuss his new book N*gga Theory: Race, Language, Unequal Justice, and the Law and the importance of eradicating anti-black bias in America. The class distinction masquerading as a moral distinction in black respectability politics. The destructive impact of these ideas on the fight for racial justice, particularly with regard to police and prisons. How Obama represents the limits of respectability politics. The need for our criminal justice system to move away from retribution and towards restoration and rehabilitation, even in cases of interpersonal violence.