Colbert's judgement in question

I found the convention episode with Elizabeth Warren & Billy Eichner painful to watch for 2 reasons. First, I understand the strategy of playing the devil's advocate, but he seemed to be going out of his way to defend Trump's convention performance while interviewing those two (who obviously were going to take the other side). It was painful to watch Colbert trying to give that hateful demagogue the "benefit of the doubt," and it was a wild misreading of his own core (anti-Trump) audience.

Second, I found it totally cringeworthy to see Colbert suggesting over and over again to Warren that she would be Clinton's VP pick. Of course, now we know that wasn't going to happen, but even then, NO ONE believed she would get the nod. Does Colbert not even really follow the news?? Warren had to keep smiling gamely while Colbert kept hinting she'd be the choice. All the leaked reports suggested there were 2 or 3 finalists, none of whom were Liz Warren. She was chosen to speak on Day One of the DNC, which was a clear indication that she wouldn't be the pick! SHE knew it, WE knew it, why didn't Colbert know?