The one that highlighted this for me was his interview with Andrew Tate where Tate said it was all completely unjustified, he was not charged with sex trafficking (or something like that) and it was all bullshit.
During, Tucker went "wow I can't believe that that's so corrupt" etc as he always does.
I'm paraphrasing because I watched it a long time ago, but you get the idea.
In any case, what did I find after looking up information on the case later? Tate was lying out his ass, and Tucker didn't try to verify anything he said to see if it was actually true.
Which I consider the job of a journalist, even if it's just through building rapport and asking good questions that give them enough rope to hang themselves with (funnily enough, as much of a midwit as he is, Rogan is usually good at doing this unless it relates to aliens and then he becomes completely useless).
I still watch Tucker, but I keep it in mind while watching. Double check what his guests say before believing it. Because, as far as I've seen, Tucker won't if it supports his own biases.
I do overall find him generally likeable and funny regardless, and do appreciate his willingness to talk to people others won't.