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Unpacking Donald Trump’s history with this fall’s debate moderators

These are the people lobbing questions at Republican Donald Trump and Democrat Hillary Clinton when they go head-to-head at the 2016 presidential debates. (Video: Sarah Parnass/The Washington Post)
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After months of uncertainty, Donald Trump has committed to participating in the general-election presidential debates.

“I expect to do all three. I look forward to the debates,” Trump told reporters in Ohio on Monday. “I think it is an important element of what we’re doing. I think you have an obligation to do the debates.”

One reason for the long delay in Trump's agreement to join Hillary Clinton onstage this fall had been complaints about the schedule — in particular, two debates that conflict with prime-time National Football League games.

But perhaps the biggest reason for the holdout: the identities of the journalists asking the questions at those face-offs. “I'll have to see who the moderators are,” the Republican nominee told Time magazine last month. “Yeah, I would say that certain moderators would be unacceptable, absolutely.” Trump had boycotted a primary debate because he was unhappy with the inclusion of Fox News host Megyn Kelly as a moderator. The stakes were lower then, but he showed he was willing to follow through on the threat.

As of Friday, the lineup was out: NBC’s Lester Holt will moderate the first debate on Sept. 26 at Hofstra University in Hempstead, N.Y.; ABC’s Martha Raddatz and CNN’s Anderson Cooper will lead a town-hall-style forum at Washington University in St. Louis on Oct. 9; and Fox News’s Chris Wallace would handle the questioning at the final debate on  Oct. 19 at the University of Nevada at Las Vegas.

Why Donald Trump might not debate Hillary Clinton

The diverse roster named by the Commission on Presidential Debates included:

  • The first African American moderator (Holt) since Carole Simpson in 1992 (Gwen Ifill moderated vice-presidential debates in 2004 and 2008, and Bernard Shaw moderated the VP debate in 2000)
  • The first openly gay moderator (Cooper)
  • And the first moderator from Fox News (Wallace)

Vice-presidential debate moderator Elaine Quijano also represented a couple of milestones, as the first Asian American moderator of a general-election debate and the first to work primarily for a digital network (CBSN).

None of the names on the list were deal-breakers for Trump. But he has tangled with all of them in the past.

The GOP nominee probably had no objection to Wallace, given that he twice agreed to participate in GOP primary debates moderated by the “Fox News Sunday” anchor. But Wallace was tough on him at those events, most memorably when he used full-screen graphics to fact-check Trump on the spot.

Wallace later told me: “Do I take a certain pleasure when I open the gate and he decides to walk down the path and I’ve got the bear trap at the end of the path? Yeah. Sure.”

Holt, who moderated a Democratic primary debate, has likewise tripped up Trump with fact-checks. In a June interview, he pressed for evidence to support Trump’s claim that Clinton was asleep at critical times during the 2012 attack on a U.S. diplomatic compound in Benghazi, Libya, and got the casino magnate to admit that his assertion might not be true.

“She was asleep at the wheel, whether she was sleeping or not,” Trump conceded. “Who knows if she was sleeping?”

Later in the interview, Holt flummoxed Trump by asking how he could say for certain that Clinton's private email server was hacked.

HOLT: But is there any evidence it was hacked other than routine phishing?
TRUMP: I think I read that, and I heard it, and somebody also gave me that information.
HOLT: Where?
TRUMP: I will report back to you. I will give it to you.
HOLT: You said it with such certainty yesterday.
TRUMP: I don't know if certainty. Probably she was hacked.

Holt isn't the only journalist with a record of throwing Trump off balance.

Trump participated in a primary debate moderated by Raddatz but faced only a few questions from her: Raddatz split duties with ABC’s David Muir, and there were seven candidates onstage. The exchanges were uneventful.

But Raddatz absolutely grilled Trump last summer in his first interview after saying Sen. John McCain (R-Ariz.) was “not a war hero.” She also confronted Trump about his rhetoric in general.

“There seems to be a pattern, Mr. Trump,” Raddatz said. “When you’re criticized or attacked, you often respond with name-calling, using terms like ‘dummy,’ ‘loser,’ ‘total losers’ on Twitter and elsewhere. You even demean some people’s physical appearance. Is that something you would continue doing if you were president? Isn’t that language beneath the office of the president?”

Trump has granted many interviews to Raddatz’s partner in the second debate, Cooper, who moderated two Democratic primary debates. When the GOP standard-bearer finally agreed to appear on CNN recently for the first time in more than two months, it was on Cooper’s program.

That interview produced more headlines about Trump’s immigration flip-flops, as Cooper pressed him to reconcile the “softening” he had described to Sean Hannity with the hard-line stance he took early in the campaign. At one point in the conversation, Trump accused Cooper of being on Clinton’s side.

“I know you want to protect her as much as you possibly can,” said Trump, who often refers to CNN as the Clinton News Network.

The hard questions Trump has faced from these moderators were well within the bounds of fairness. But Trump is not one to limit himself to rational bias claims. Even those fall moderators who have been involved with a presidential debate in past cycles can expect to oversee face-offs unlike any they have handled before.

What Donald Trump is doing on the campaign trail

MANCHESTER, NH - NOVEMBER 7: Republican presidential candidate Donald Trump speaks during a campaign event at SNHU Arena in Manchester, NH on Monday November 07, 2016. (Jabin Botsford/The Washington Post)

This story has been updated.