You need to look at it from the viewpoint of the low information voter, not the politically engaged Freeper.
I think that is how the low information voter sees it. The system is against me. The system is against Trump and for Hillary. Trump says he is on my side, and Hillary says same thing. I believe Trump.
The low-information voter doesn’t care about the details that Holt challenged Trump on. Whether Trump opposed the Iraq war, or when, and the other details are not the important parts of this decision to most voters who are just tuning in. The narrative really is what matters, as liberals always say, and Holt helped the narrative.