I originally wrote and posted this at the end of 2018. I'll add some current [August 2022] thoughts at the end.
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I've long made a habit of listening to Michael Medved and I've often read his columns. I have a couple of this books.
While he seems to be personally very conservative (as in his personal life), he hasn't been a "the Republican way is the only way; screw Democrats" kind of guy when it comes to politics. He's tried to be fair to disagreeing callers Left of him, and to those Right of him (and there have been a lot of those lately!)
He has given his Democrat/Leftist friends plenty of air time and is generally very polite, trying to find common ground with just about anyone. He has always said he wants the President to succeed no matter who it has been, so that has included Obama.
I first thought things might change for him in 2016, when he refused to endorse or vote for Trump. Mind you, he didn't vote for this classmate, Hillary, either. Salem talkers who did endorse Trump were sent on a tour that year to try to get out the vote. Medved did participate in Salem townhalls, at which many in the audience were disappointed at his refusal to endorse Trump.
Since Trump was elected, Medved has praised the things the President has done that he likes and criticized (usually constructively) the things he hasn't liked, and there have been plenty of those.
The writing was on the wall once Sebastian Gorka, one of the many people with Trump Administration experience, started filling in for various Salem talkers when they were away from their own shows. Gorka is very much in Trump's corner, and not just because that's who happens to be the (Republican) President. Gorka has an accent and voice some listeners find appealing. I did often listen to his guest hosting stints, whereas I listen to very few guest hosts. Gorka expressed, on-air, his enjoyment of hosting.