Team of Vipers: Miss-Selling a Memoir

The copywriter Eugene Schwartz was a master growth hacker. Sometimes, he wasn’t sure if a product was worth manufacturing — so he’d run ads for it and sell it anyway, and just cancel the orders if demand wasn’t there. Sometimes, it’s the marketing campaign that creates the

The copywriter Eugene Schwartz was a master growth hacker. Sometimes, he wasn’t sure if a product was worth manufacturing — so he’d run ads for it and sell it anyway, and just cancel the orders if demand wasn’t there. Sometimes, it’s the marketing campaign that creates the product, rather than the other way around.

Right now, this is happening in publishing: anyone who worked in the White House in the last two years has a great marketing pitch. “We’re going to get a Twitter account with 58 million followers to tweet about our new book!” Now, all they need to do is write a book. As we get closer to 2020, the trickle of bridge-burning memoirs will turn into a deluge.[1] Some of them are good. Some of them are only fit for true political junkies. Omarosa’s is the politics junkie’s equivalent of turning the baggie inside out and licking it.

The only problem with the Trump-tweet marketing plan is that a positive tweet from Trump isn’t all that exciting. A negative tweet, though; that gets people going. In the last few years, marketers have learned to leverage Spitefully Partisan Consumption, where you buy something specifically because you’re pretty sure it would make other people mad. (This is bipartisan; it’s part of the pitch for gun ownership and coffee, as well as children’s books and index funds.) So, if you’re a book agent, you’re stuck — you have to find someone, anyone, who worked in the White House and wants to say something bad about the President.

Which is not hard. In fact, based on the volume of leaks, it would be a chore to find a White House staffer who only had nice things to say about Trump.

So there are two explanations for the media blitz around the newly-released Team of Vipers:

  1. The marketing people didn’t actually read it.
  2. They read it, and they hoped their target audience would all buy a copy before without reading any reviews.

Because Team of Vipers, while it fits into the genre of dishy bridge-burning books people people with White House access, the author seems to be a basically affable guy who mostly agrees with, and likes, Donald Trump. This is not the impression I got from the media coverage. Politico says “every warring faction has come together” to oppose it. The Huffington Post has embarrassing excerpts. Axios highlights the enemies list.

But here and there in Team of Vipers, Sims drops some subtle hints about his perception of Trump.

Lacking any filter, he’d make the same observation to the Queen of England that he’d make to a construction worker at one of his hotels. To those open to him, this can be one of his most endearing qualities — he just is who he is.

He’s the most self-assured person I’ve ever been around. He’s the alpha dog in every conversation I’ve ever seen him engage in, and he owns every room.

He refers to a pivot — interviewing Trump for his radio show, he asks about religious liberty and gets an answer about the unpopularity of “Merry Christmas” — as “far from the only example of Trump’s marketing genius.”

“The thing I remember most about his demeanor,” Sims says of Trump on the day the Access Hollywood tape hit, “was how remarkably calm he was… The trump I saw was somewhat defiant, but more than that, relaxed — placid… the entire country was coming unglued about Trump and he didn’t even seem flustered.”


One quality not often attributed to Trup was consistency… there was something to be said for someone who just keeps going, no matter what. When it’s a good day, he gets up and grinds it out. When it’s a bad day, he gets up and grinds it out. Then he does it again. Then he does it again. And again… Yes, Trump could be impulsive, even reckless. Sure, he operated almost entirely off of gut instinct. But he was also the most methodical, patient person I’ve ever seen in the midst of a crisis.

Cliff Sims, author of the latest devastating expose of Donald Trump is — actually a huge Trump fan!

So why did he write a damaging book?

Maybe Sims is a political naif. On the other hand, before he joined the Trump campaign, Sims wrote a political blog about Alabama news that brought down the governor. Maybe Sims had some sort of conversion experience, and decided he wasn’t so conservative after all — if so, it was a lengthy conversion, since the governor he took down was a fellow Republican. Or maybe, most likely, Sims was and remains a true believer, and he wrote a book dishing on everyone adjacent to Trump. He didn’t write the book to trash Trump; in his view, at least, he wrote a book exhorting Trump to take out the trash.

The last version makes the most sense.

In which case the book’s marketing is both deeply dishonest and tactically brilliant. The published excerpts can be read in two ways: you can look at Trump’s leaker crackdown, for example, as dictatorial behavior, or you can look at it as a President trying to stop leaks. He’s not the first chief executive to do that — when I worked at Yahoo, I overlapped by exactly one day with Carol Bartz, who once threatened to drop-kick leakers to Mars. Politico ran an extended excerpt involving Trump’s negotiations with Republican legislators trying to repeal Obamacare. If you like Obamacare, this is sinister; if you don’t, this is just politicians doing their job.

By spinning the book as an indictment of Trump rather than an indictment of people who got in Trump’s way, Sims’ publishers were able to get the ideal PR placement: a negative tweet from Donald Trump, which happened while Sims was live on CNN. Nice job! Twitter is TV’s Greek Chorus, but there’s one tenor who sings so loudly it breaks the fourth wall.

The Game Theory of the Leak

One thing I didn’t really get before Team of Vipers was the nature of The Leak. Why are people constantly trashing their coworkers to the media?

DC reminds me of the Souk Al-Manakh crash. For a brief period in the 1980s, Kuwait had the third most-valuable stock market in the world. Like all bubbles, it was sustained by credit; in the Kuwaiti case, by post-dated checks. As long as everyone is writing checks they can’t back, asset prices rise, and by the time the checks come due you can pay them. If everyone is doing it, everyone has an incentive to play along.

DC is like that, but with reputations: everyone takes credit for everything. Any time a law gets passed, twenty different people modestly claim that they were only half responsible. This creates a massive bubble in, well, credit. And journalists can pop it, by writing an article on how so-and-so is really only as important as his job title implies, if that, or that such-and-such used to have a lot of pull but now nobody returns his calls.

To survive in DC, you need the leverage of apparent influence, and you can’t let anyone pop your bubble. To maintain this juggling act, you give the prospective bubble-poppers ammunition to go after someone else; if you’re a source, you won’t be a victim.

This gives two equilibria: either nobody leaks, so there are few damaging stories floating around, or everybody leaks all the time and nobody trusts each other.

The ubiquity of leaks has had the paradoxical effect of making the Trump administration the most open and transparent presidency of my lifetime. It’s not intentional; they just hate each other.[2]

This theory of leaks gives a leak-averse administration a couple angles, other than the obvious one of catching and penalizing leakers. One thing they can do is focus on lots of small, technocratic tweaks; if I worked in DC, I would probably gravitate towards some incredibly boring regulatory topic in the hopes that nobody would bother with media assassination. Another related option is compartmentalization: if you have small teams of people who spend all their time on a single project, you have fewer people to leak, and fewer people reduces the odds that any two people in a meeting will hate each others’ guts. You could also staff your administration with people who will say outrageous things on the record. Finally, you can just make lots of spontaneous, last-minute decisions, so there’s nothing to leak. The last two seem popular right now.

The Book

The way to read a Trump book is to imagine he’s some important historical figure whose name you recognize, but with whom you don’t have any emotional associations. Louis XIV, Peter the Great, Enrico Dandolo, a Henry or Richard the Nth who didn’t get a Shakespeare play. You assume some people liked him (or he wouldn’t have been in charge); you assume some people hated him (you try keeping more than half the country happy), but you mostly want to know what happened. To render a popular bumper sticker twice as inclusive: nobody who was well-behaved ever made history.

So I tried to read it as if I don’t have an opinion on wars, taxes, health care, civility, immigration, or whatever else.

This turned out to be stupid and impossible — of course those biases matter. The difference between bold and reckless, between rakish and boorish, between charisma and demagoguery — it depends entirely on who you’re rooting for.

We’ll get a good Trump book some time in the next few decades, but it won’t use the name “Trump.” It’ll be set in Ming China or Renaissance Florence or an asteroid-mining colony. It’ll be written by a literary figure who, a few years hence, will suddenly shock everyone by registering as a Republican — a Mamet, Bellow, or Helprin.

Sims says very little about Trump that’s not already part of the story — yes, he’s obsessed with his media coverage (Sims is impressed with the volume of news he reads); sure, he makes impulsive decisions (many of which Sims decides were smart after all); and of course he’s surrounded by people he can’t trust (many of whom, coincidentally or not, are Sims’ internal rivals). The most striking detail to me was how much care Trump takes in his media presentation. In an older political system where legitimacy is based on forced, kings were expected to lead their forces into battle; now Presidents who derive legitimacy from popularity know what camera angle makes them look best.

The meat of the book is about the internal politicking at the White House. If I had to diagnose a root cause, it would be that Trump had some loyalists, but not enough to staff every job, so he hired people from the RNC. He basically put together the two subsets of the Republican party that most loathe each other, and asked them to work together. The closest parallel I can think of is when a company gets bought by a private equity sponsor: you have a small group of people in charge, who feel like they just won, and a lot of people reporting to them who wonder if they just lost. If Trump and Romney kept their views and personalities, but switched careers, we’d live in a very different world.

Within the Trump loyalist circle, there’s another division: the intellectuals and the operators. The intellectuals read a bunch of Machiavelli; the operators are the ones who were born to be Borgias.[3] They both seem to understand each other. Operators recognize the intellectuals as just another egghead who will be easy to crack. The intellectuals hear about what Bannon or Conway did and say “That’s exactly like Agathocles of Syracuse!”


I changed my mind about very little after I read Team of Vipers, although I picked up some supporting anecdotes for my pet theories. Mostly, I came away from the book liking the author: Sims seems earnest, he has his beliefs, he ultimately took a big risk that didn’t pay off in quite the way he’d hoped, but he mostly kept track of what matters. Sims and I disagree on important matters of policy, but he sounds like a fun guy to argue with.

On the other hand, how reliable a narrator is he? “Everyone who made it into the Trump White House was a cruel sociopath (except me).” Well, that’s what a decent person would say, and that’s what a sociopath would say, so let’s consider our base rates and thus consider the possibility that Sims is a bad dude.

If he’s a bad guy, he’s probably lying at various points in the book, but that just means the genre’s wrong: it’s historical fiction set in an extremely recent part of history.

So Team of Vipers is a very indeterminate book. It’s not what it was sold as, but it was sold as something there’s a lot of demand for. The author might be a decent guy or the book might be his latest stiletto to the back of his rivals. Uncertain, outrageous, but ultimately hard not to like — it’s the perfect encapsulation of American politics in 2019.