Update: We have closed the submission form after the news that White House press secretary Sean Spicer has resigned. If you’re here from the Read These Comments newsletter, you can still participate in The Guesstimator by suggesting to us what the next question should be by clicking here.

Given that Donald Trump kept himself in the limelight for years with “The Apprentice,” it’s surprising that the president has yet to turn to anyone in his administration and utter “You’re fired!” Just as surprising, with the exception of former national security adviser Michael Flynn, no one in the president’s innermost circle or Cabinet has resigned.

Which Trump staffer do you think will be next to fall or flee? Read on. The reader with the best guesstimate will receive a free “Democracy Dies in Darkness” T-shirt. Congratulations to last round’s winners, Mo Dodge and Sara Wisner!


At one point or another, observers believed that staffers such as Stephen K. Bannon, Kellyanne Conway and Sebastian Gorka were on the verge of leaving. Press secretary Sean Spicer’s departure has been expected at several points.

And the next resignation or firing only seems a matter of time. Between loans and back channels, Jared Kushner is reportedly under special counsel Robert S. Mueller III’s microscope. Commerce Secretary Wilbur Ross’s interminable teleconference babbling to a Christian Democratic Union meeting in Berlin made him a laughingstock in Germany — and we know that the president is not amused by public mockery. National Economic Council director Gary Cohn has angered conservatives who believe him a moderating force on the president.

Something — or someone — has got to give. You would think.

Timothy Naftali, who formerly ran the Richard Nixon Presidential Library and is now a clinical associate professor of public service at New York University’s Robert F. Wagner Graduate School of Public Service, says that making such a call is nigh on impossible. He sees interlocking parts creating a kind of administrative chain mail that’s tough to pierce (though important to assess):

Patrons and alliances always matter but especially in an administration dominated by a volatile personality: National Security Adviser H.R. McMaster seems to work very well with Defense Secretary Jim Mattis and might get his protection were President Trump to sour on him — plus there is no reason to doubt that Mattis, who has a lot of delegated authority, enjoys anything less than the full confidence of the President. Health and Human Services Secretary Tom Price seems connected to Vice President Michael Pence. Chief of Staff Reince Priebus is apparently close to House Speaker Paul D. Ryan. And Treasury Secretary Steven Mnuchin is a Trump guy. Secretary of State Rex Tillerson, however, is an enigma — his worldview, his administrative loyalties, his hot buttons.

Predicting Trump may be a fool’s errand, but that hasn’t stopped our other experts. 


David Boaz, executive vice president of the libertarian Cato Institute: “Rex Tillerson spent 40 years rising to the top of Exxon, an organization that made decisions in an orderly manner, based on research and study. He will soon tire of working in a chaotic organization, in which he can’t appoint senior staff, decisions and policies are subject to being overridden on Twitter, and the boss’s son-in-law usurps his authority.”

Ron Klain, former chief of staff to Vice Presidents Al Gore and Joe Biden: “I think Attorney General Jeff Sessions will be the first to go. Yes, Spicer will lose his podium, but he’ll still have a White House job. And Priebus remains at risk, but hangs on. I think Sessions is likely to go because the number one thorn in Trump’s side is the Russia investigation, and the only way to exercise any leverage over it is with a new attorney general. Sessions is recused, and Trump has tweeted his anger at the official reports to deputy attorney general Rod J. Rosenstein, who has ruled out firing or constraining Mueller. The only way for Trump to regain any control is to have Sessions leave, and replace him with an AG who is not conflicted — making that new Trump pick the person to whom Mueller reports, who can try to impact Mueller’s work — or fire him if that is what Trump wants.”

Bruce Ackerman, Sterling Professor of Law and Political Science at Yale: “First to go, Rex Tillerson. He is regularly humiliated by Trump, and his effort at State Department reorganization has failed to get off the ground — isolating him from the area specialists who could support his quasi-sensible impulses with serious analysis, making it easy for the president’s ignorant cronies, like Jared Kushner, to dominate crucial diplomatic initiatives. There is nothing left for him to do but resign.”

The Guesstimator: While Spicer may be in hot water, we predict he’s getting kicked upstairs, not out the door. Instead, we see a near-term exit for Reince Priebus. In the second week in June, Politico reported that Trump had berated his chief of staff for the White House “mess” and was giving him until the Fourth of July to clean it up. That was supposed to coincide with Senate Majority Leader Mitch McConnell’s deadline for health reform passage, so the reckoning obviously has been delayed. But Priebus, with apologies to John Donne: Ask not for whom the ax swings, it swings for thee.

Who do you think will be first out the door? Submit your own guesstimates for this question below. (If the form is not displaying, click here.) The reader with the best guesstimate will receive a free “Democracy Dies in Darkness” T-shirt. (Want to suggest a question for the Guesstimator? Click here.)