Stephen Colbert’s Trump Leaks Segment Went So Far, Even He Was Uncomfortable

The jokes were raining down on The Late Show Monday night, and most of them were hitting the president. Stephen Colbert called Trump “leaker in chief,” which might have been even funnier if that weren’t taken straight out of a New York Times article quoting the president’s own aides.

“Donald Trump is obsessed with his staff leaking information. You know how I know that? His staff leaked that information to The New York Times,” Colbert said, starting off a series of jokes at the president’s expense. Colbert continued, at times reading from The Times piece:

"West Wing aides are instructed to drop their personal phones into small storage lockers when they come to work." Wait a second, they’re taking away the phones of everyone except Donald Trump? How does that work? How does that help? That’s like saying, "No one can bring knives to work, except you, O.J."

That one got Colbert an uncomfortable laugh from the audience, but the late night host carried on. “If this sounds paranoid, it’s only because it is,” Colbert said. “Former Trump aides say the president ‘thrives on a sense of dominance and control of his environment’ so much so that he ‘has a longtime fear of having his food contaminated.’ Yes, and for good reason. Once he was eating what he thought was a safe meal and he found a vegetable in there.”

The Late Show with Stephen Colbert on YouTube

But it wasn’t just the president who came under fire. It was the entire administration. “The behavior of some of his staff has been extreme,” Colbert started his joke. “The ‘junior aide was found to be taping meetings with Mr. Trump and playing them to impress friends.’ Really? I find it hard to believe that someone who works in the Trump administration still has friends.”

Then came the president’s title of the night, and one of the most uncomfortable — if funny — jokes about the country’s commander in chief. “During the campaign, Trump aides were afraid that whatever they said to him would end up in the press, and behind his back they called him 'leaker in chief.'”

Then Colbert came back into the shot looking physically uncomfortable. “Fight it,” Colbert said to himself. “Fight it, Colbert, it’s not worth this.”

But then the joke won out. “More like 'leaker on sheets' — damn you, Satan!” Colbert said, mockingly upset about the slip. “Damn you, Satan. Get thee behind me.”

The Late Show With Stephen Colbert

Colbert tried to put his jokes, and the article, in more context. “I know I talk a lot about how the president has become a delusional megalomaniac who lives in a reality of his own making, but that’s not fair,” Colbert said. “Trump was that way before he was president too.”

For an example, Colbert brought out an interview to prove it. It was with Pete Davidson of Saturday Night Live who talked about when Trump hosted the show. Davidson claimed Trump faked a phone call during the last table read and told the cast that his book had been listed as number one.

Colbert said his answering his finger phone must have given it away (and then reenacted Trump talking on a finger phone — something you’ll have to watch the video to see). “Not only was this rando phone call apparently faked,” Colbert said, “but the book he’s referring to, Crippled America, never made it to number one on the bestseller list. It was like Moscow, Trump just sat there while someone else went number one.”