In this essay, I look at the problems facing progressives and those on the political left in the United States in participating in political analysis and debate in mainstream journalism and the news media. I focus on radio broadcasting, as this is where much of political discussion takes place in the United States. Radio broadcasting is the least expensive of the media for production and reception, is ubiquitous, has adapted itself to the Internet, and is uniquely suited for locally based programming. I leave aside the matter of the Internet, as this is an issue I address in detail elsewhere; while the digital revolution is of indubitable importance, it does not alter my basic argument appreciably (McChesney 2013). I also stay away from television, cable TV news networks in particular. While those channels are important, they too do not affect my core points. I look specifically at my own experience at hosting a weekly public affairs program on an NPR-affiliated radio station in Illinois from 2002–2012. This was, to my knowledge, the only NPR series ever hosted by a socialist in the network’s history. But before I draw from my personal experiences, some context is necessary.