Ride or die.
Support The Bulwark.
  Join Now

“Team of Vipers” Is Actually a Mash Note to Trump

Cliff Sims’s tell-all memoir is mostly about how great Trump is and how badly served he’s been by a bunch of low-level nobodies.
February 5, 2019
Featured Image
(Illustration by Hannah Yoest / Shutterstock / photos: GettyImages)

Regrets, Cliff Sims has a few. But then again, too few to mention.

The memoir he penned about his time in the Trump White House, Team of Vipers, is presented as a good-faith attempt to distinguish himself from his tell-all peers by offering the view from the White House’s lone honest man. Sims fancies himself not a “sycophant” nor a “hater” but a simple Alabama boy who came to Washington certain that his moral compass was true until he was changed by proximity to power. It’s a tale as old as time, really.

He charts out a careful story designed to convince readers, the media, and possibly himself that the vipers are the people around Trump. The president himself remains, in Sims’ telling, a lamb.

This misdiagnosis is apparent from Sims first meeting with then-candidate Trump. At the time he’s humble blogger and talk radio host in Alabama, nervously excited that Hope Hicks has granted him an interview in the summer of 2015 before Trump’s massive speech in the state. Before the interview Sims writes about how he is the son and grandson of a preacher and “wanted to get Trump talking more about his faith… Needless to say, I was raised to believe that faith is the foundation of character. At the time, my faith was one of the reasons I struggled with Trump’s unexpected rise,” he writes.

So Sims confronted Trump in the interview, asking him first about abortion and then about faith. On the former, Trump tells a story about an unnamed family that was going to terminate their pregnancy and didn’t: “The child has turned out to be so incredible. Every time I see them they say, ’Can you believe that we were thinking of . . .” When asked about faith and religious liberty, Trump pivots to—hand to God—the War on Christmas.

Given Trump’s history of making up fake characters, the bizarre prospect of a person bringing up the time that they almost aborted their child every time they see Donald Trump, the fact that the War on Christmas answer came in the summertime, and Sims pre-interview wind-up about his concerns about Trump’s character, you might expect this to be a foreshadowing of problems that would occur in the White House. But no. The abortion answer he “didn’t find to be insincere.” And the “War on Christmas” clip was instead presented as an example of Trump’s marketing genius. The interview went viral and Sims got hooked on Trump.

This disconnect repeats itself over and over again. Sims touts a moment of ethical clarity or a higher purpose that are in obvious conflict with the ethos of Trump, yet this tension never seems to occur to him.

Consider that Sims spends time in the book reflecting on how he helped take down Alabama governor Robert Bentley by exposing his extramarital affair, which cut against “Christian witness.” Yet the subject of Trump having paid off a porn star paramour while his wife was home with a newborn doesn’t faze him and is barely mentioned in the book, despite it being a massive news event while Sims was on the communications team. Sims describes the proudest moment of his time in the White House as General Kelly talking to the staff about the calls he received after the death of his son in combat. But he glosses over the fact that the same day, Trump used Kelly’s son’s death in a bizarre boasting that he was better than Obama at calling gold star parents to console them on the deaths of their children.

This is a lot of sleight of hand for a book that’s supposed to be telling all.

Upon entering the White House Sims writes that his “senses were heightened by the weight of history all around me.” Five pages later he is writing a draft of Sean Spicer’s infamous (and lie-riddled) first press conference remarks about the size of Trump’s inaugural crowd. Seven pages after that he is reveling over how seriously the president took White House decor after Obama left the carpet a “dingy, yellowish color.” And after that there’s an extended vignette about the president’s “red button” which lets him call for a Diet Coke. This is capped by Trump giving Ben Carson the red-button treatment because he was bored with hearing the secretary’s plans for addressing poverty and literacy.

The chapter ends with Sims waxing about the majesty of a conference call with astronauts in the space station and a retelling of the story, behind the story, of how Spicer stole a mini-fridge from the younger comms staffers.

For Sims, the weight of history turned out to be incredibly light.


Team of Vipers has been sold as Straight Talk about the Trump administration. But the book contains almost no serious reflection about Trump’s flaws and obsesses mostly about the duplicitousness of random staffers who, by total coincidence, are largely Sims’ internal rivals.

To demonstrate how reliable Sims is on Trump himself, he affirmatively defends the travel ban, the Comey firing, and the use of Wikileaks in the campaign. He does not believe there was any wrong-doing related to Russia. He blames Paul Ryan for the failure to repeal Obamacare. He likes Trump’s tweets. He divulges no personal views about the Access Hollywood tape. He repeatedly defends Trump against charges of racism and tries to explain away Trump’s response to the white supremacist march in Charlottesville and then questions the motivations of other staffers who contemplated jumping ship in that moment. He writes that Trump never treated women as badly as Hillary Clinton did. Trump is depicted at various times as, humbled by the presidency, having a desire to be a “uniting figure,” and “the bravest person I’ve ever seen in the face of public scrutiny.”

If this is Sims’ unvarnished view of the president, just imagine what it looked like back in 2016 when he was really trying to shine Trump up to get a job.

Instead of pointing out the successes and failures of the commander-in-chief, Sims gives us a lengthy accounting of the shortcomings of Michael Short.

Haven’t heard of him? Short is a midlevel comms staffer whose main crime was quitting the campaign around the time of the Access Hollywood tape. Even Sims’ juicy story about having evidence that Kellyanne Conway leaks to the press is followed by him defending her leaks as being different in character from the really problematic leaks from the national security team.

That’s when you realize that, despite everything, Team of Vipers is actually not much more than Trump fan-service: Sims believes that the president is great; his family is great; most of his closest advisers are great. The only reason this administration hasn’t been a roaring success is because of the low-level snakes nipping at the great man’s heels. In that sense, even Chris Christie’s book is tougher on Trump because it fingers high-level people such as Jared Kushner and Steve Bannon, and admits that Trump is a terrible judge of character and ability.


The only substantive reflection in the entire book is on the issue of refugees.

Some years ago, Sims made several trips to refugee camps in the Middle East and was moved by their plight. His concern seems entirely sincere. Yet the only action Sims seems to have taken on the subject was conversation with Steven Miller where Miller tells him that President Trump’s goal is for the United States to not accept a single refugee. Sims then laments that the faith leaders who advised Trump didn’t press him on the subject.

If Sims mentioned his concerns about the cratering refugee resettlement numbers to Trump, or Kushner, or anyone else in power, he doesn’t mention it.

In the end what Sims seems to take with him is a koan from Kellyanne Conway, who tells him that “There’s a difference between what offends you and what affects you.”

This fortune-cookie wisdom is, of course, a logical fallacy. And yet it is the overall moral sense of Sims’ book. Somehow, he seems oblivious to the truth that what merely offends him might actually affect others.

The final chapter of Team of Vipers opens with a self assessment of the author’s time in the White House: He allows that he had been ambitious, unkind, quick to seek revenge, too quick to pass judgment on his enemies while granting himself moral superiority in the process. It ends with Sims bragging about the time where he showed President Trump polling numbers on kneeling NFL players that highlighted how popular his call to owners to “get the son of a bitches off the field” was and Trump responding with how entertaining he expects it will be to attack Democrats on that issue in 2020.

Regrets, indeed.


Five Additional Essential Nuggets

(1) Trump on the gravity of being elected president:

On the verge of his ultimate victory, a historic repudiation of all of his critics, a moment when he could have taken the high road as his place in history was assured his first thought was retribution. “When I get to Washington I’m gonna shove it up Kasich’s ass!” he declared.

(2) Jared Kushner’s “key man”:

“This is our key man right here,” Kushner told me, putting his hand on Stephen [Miller’s] shoulder. “If we took out key-man insurance on any one person on the campaign, it’d be him. We’d be lost without him.”

(3) Sims claims Spicer screwed him out of $30,000 per year:

Though we’d gotten along fine during the campaign, now that his job was assured, Spicer never answered a single one of my phone calls during the transition, and called me only once. He offered me the job of Special Assistant to the President and Director of White House Message Strategy, told me I’d be working in the West Wing and laid out what my salary would be. I wouldn’t find out until I moved to D.C. that my salary was actually thirty thousand less than Spicer had promised in that phone call. When I broached the subject with him, he told me, “you should be honored to even have a chance to work for the President” and I should “go work someplace else” if I didn’t like it.

(4) Mooch was really into being Catholic:

You might recall a classic line from Scaramucci’s 11-day White House tenure, when he told the press corps that it upset him ‘as a Roman Catholic” that they would leak news of a staffers termination before the staffer had been told. Well turns out the leaker who sinned was actually. . . Anthony himself. . . .

The story’s lead was all about the firing of Michael Short, which obviously had not happened yet. “I don’t know why they’re reporting this,” Scaramucci snapped . . . “I don’t know why she would do this,” he complained. “I told her not to post it until nine!” I glanced at my watch. “Mooch it’s 9:15.” . . . Shortly thereafter Mooch went on another tirade vowing to rid the White House of leakers. “This is actually a terrible thing. Let’s say I’m firing Short today. The fact that you guys know about it before he does really upsets me as a human being and as a Roman Catholic,” he told reporters. “I should have the opportunity if I have to let somebody go to let the person go in a very humane, dignified way.”

(5) Sims does not think Sarah Sanders is a liar:

These gymnastics with the truth would tax even the nimblest of prevaricators, and Sarah was not that. She was not a natural liar and, I believe, in most cases she was not an intentional one.

For some people, that sort of thing seems to come pretty easy.

Correction: An earlier version incorrectly spelled Mr. Sims’ name.

Tim Miller

Tim Miller is The Bulwark’s writer-at-large. He was previously political director for Republican Voters Against Trump, communications director for Jeb Bush 2016, and spokesman for the Republican National Committee.