CHRIS HAYES (HOST): One of the other things in your piece I thought was really interesting was the relationship with Trump and Roger Ailes of Fox, which as been one of the more fascinating sort of subplots of this campaign season. You talk about a sort of acrimonious departure of one of Ailes' top lieutenants, a guy who sort of threatened to spill the beans, and Trump's role in that exit. Tell me that story.

GABRIEL SHERMAN: It's really fascinating and this sort of helped me connect the dots to figure out why Trump has been able to do something that no other Republicans have done, which is to go up against Fox News with impunity and kind of brazenly challenge Roger Ailes and Fox News. And what I learned is that, in 2013, when Roger Ailes fired his longtime PR confidant, who was privy to the darkest, most interesting controversial secrets about Fox News, Donald Trump played mediator to help them work out a severance deal for Roger Ailes' PR confidant, and learned all of the dirt that he was going to spill, that Roger Ailes ended up paying millions of dollars to keep secret. So now, Donald Trump goes into this fight knowing that Ailes presumably knows that he knows things that he doesn't want public, and really that's why, although you've seen Fox fight back, it has not been a scorched earth campaign. Roger Ailes has not turned over Fox News' airwaves to attack Trump 24/7, the way he's done against his other political enemies.

HAYES: So, it is your supposition or implication at least that the knowledge, the sort of secret knowledge Donald Trump has, the dirt he has on Roger Ailes has acted as a kind of shield throughout this campaign in terms of the coverage he's getting from that network?

SHERMAN: You know, that was my -- that was basically what emerged from my reporting. Now, it's important to point out, Trump himself did not say "I'm using this against Roger Ailes. He did tell me that he mediated this private negotiation. I do know from my reporting that the dirt was very damaging, so it stands to reason that all of these parties know what Trump knows and that explains why he's been able to get this far with attacking Ailes.

Related: 

Talking Points Memo: Report: Trump Still Has Major 'Bombs' To Drop In Flame War With Fox News

Previously:

Report: The Trump Campaign Is Tearing Apart Fox News

Journalist Gabriel Sherman: Roger Ailes' Executives “Are Doubting His Judgment” In Debate Conflict With Trump

Following Trump-Fox Standoff, Trump Says He Loves Fox And Has “Great Respect For Roger Ailes”

The Donald Trump Vs. Fox News Clusterfuck, Explained