Pop culture obsessives writing for the pop culture obsessed.

Former Trump aide Cliff Sims shares his regrets—like putting Stephen Colbert on Trump's enemies list

Chris Sims, Stephen Colbert
Screenshot: The Late Show

Stephen Colbert welcomed one Cliff Sims to The Late Show on Monday. And while Colbert is always here to give airtime to anyone dishing manure-rich dirt on the Trump White House, the fact that the unassuming Sims (who spent a year-and-a-half as “director of message strategy”) got first guest position over music legend Paul Simon might be considered odd. At least until, at the end of the interview, Sims—author of the (latest) Trump administration tell-all, Team Of Vipers—admitted to Colbert that, of all his regrets about serving under Donald Trump, one of his greatest is helping compile Trump’s “enemies list.” And that, as Colbert reacted in mock disappointment, the Late Show host and nightly Trump-basher was only slotted at number two.

Before that fleeting bit of gossip, however, Colbert did an admirably sly job of holding Sims’ feet to the fire about his time serving (some would say abetting) Donald Trump’s assault on everything that’s theoretically decent and admirable about the United States of America. While Sims was forthright about being one of the titular “vipers” who, he says, slither in self-aggrandizing gamesmanship around the White House halls of power, he also explained that he’s still on board with a lot of Trump’s “accomplishments.” Sims cites economic growth (which Colbert punctured by asking if Sims’ messaging included the farcical claim that Trump’s billionaire giveaway tax scam would “pay for itself within a year”), and Trump “pulling us out of some of these foreign engagements.” (Colbert got Sims to admit both that Trump’s scattershot approach has horrified the Pentagon, and that Trump hasn’t actually followed through on his announcements thereabout.)


Still, Sims said his book was about coming clean himself as much as vilifying those still serving Donald Trump, calling himself “ruthless,” “a coward,” and “self-serving” during his time in the administration. Colbert noted that Sims’ book talks about Sims letting down his Christian faith as being one of the things that most galls him about his time in the White House, although the author doesn’t get into just where said faith buoyed him through his 500 days of support of Donald Trump after Trump’s defense of Nazis after Charlottesville, putting babies in cages, calling Mexicans rapists, endorsing a pedophile for Senate, promoting birtherism, attacking the LGBTQ community, or, hell, here’s a list. And another. At least Colbert got some of the juicy details he was looking for, including the time that Sims—tasked with crafting the defense that White House spokesperson Kellyanne Conway wasn’t an inveterate leaker—watched in amazement as Conway leaked inside information to the press on the iPhone she had synced to the very laptop he was using. As Sims himself proves, Donald Trump truly hires only the very best people.

Share This Story

About the author

Dennis Perkins

Contributor, The A.V. Club. Danny Peary's Cult Movies books are mostly to blame.