This exploratory qualitative study utilizes a conceptual content analysis to better understand the prog-left media ecosystem. Prog-left media is short for the progressive left media in the U.S. The use of the term, “progressive” distinguishes them from the center left of the American political spectrum. We performed two rounds of coding on seven prog-left programs that appeared between June 2019 and January 2021. During the second cycle of coding, we used pattern coding to categorize the codes into themes: Guests, Neoliberalism, Professional Managerial Class, Elites and Elite Culture, and Mainstream Media. We then compiled these themes into four findings: the prog-left programs have diverse formats, but reoccurring guests; prog-left programming largely centers on critiques of neoliberalism; the prog-left programs frame U.S. political parties as anti-working class servants to wealthy elites; and the prog-left programming illuminates and denounces the influence of elite culture on U.S. institutions. This study contributes to the advancement of the application of media ecology theory in digital spaces, and provides a rich understanding for future research on the prog-left media ecosystem