Trump is not going to win.” That’s what podcaster Jon Favreau declared in 2016 to The Hollywood Reporter, two weeks before Donald Trump did just that. Had Trump’s Democratic opponent, Hillary Clinton, taken the presidency, Favreau and fellow ex-Obama staffers Jon Lovett and Tommy Vietor probably would have ended their popular political podcast, then called Keepin’ It 1600. Instead, the three friends found themselves, on the morning after the election, pushing Lovett’s car down Sunset Boulevard after they ran out of gas en route to recording a new podcast. That’s when, as Favreau recalls, they decided, “We should have a media company.”
The company they went on to build, Crooked Media, is an unabashedly left-leaning organization whose flagship podcast, Pod Save America, has been downloaded 321 million times and is…