David Letterman Confronts Kim Kardashian West About Working With Trump

David Letterman knows how to make a splash. Over three seasons of his Netflix interview series My Next Guest Needs No Introduction—the most recent of which drops this Wednesday—the former Late Show host landed a majorly famous guest for each premiere episode.

First came former President Barack Obama in early 2018, giving his most in-depth on-camera interview since leaving office to the long-bearded Letterman. Last year, season two opened with a fiery sit-down with Kanye West, who both said he felt “bullied” by liberals for supporting Trump and admitted that he had never voted in his life. “Then you don’t have a say in this,” Letterman shot back to cheers from a crowd that included the rapper’s wife Kim Kardashian West.

Now, it’s that reality show star-turned-fashion mogul’s turn to join Letterman on stage for yet another fascinating conversation to open season three.

Letterman begins the interview, which was taped early this year, before the coronavirus pandemic began, by admonishing the Kardashian clan for arriving late to the theater. “Oh for Christ’s sake, the showtime’s not on the ticket?” he asks jokingly as Kris Jenner, Kourtney Kardashian and Khloe Kardashian file in. An empty seat next to Jenner is soon occupied by an even later Kanye West.

The interview itself begins with genuinely curious questions from Letterman about hair extensions before the host actually submits an apology of sorts for making fun of Keeping Up With the Kardashians in his Late Show monologues back in the day. “Well, here we are and we’re not laughing now,” he says, pointing to the overwhelming success her family has achieved. He also rejects the whole notion that Kardashian is “famous for being famous” because he admits there is some skill involved in making a show like theirs work.

From there, things quickly take a turn towards more substantive topics, including her father’s role in the O.J. Simpson trial—she still won’t say if she thinks he’s guilty out of respect for his children—and Kardashian’s most recent crusade as an advocate for prison sentencing reform. Which, of course, leads to her unlikely alliance with President Donald Trump.

“Hopefully, for the next multiple administrations, I’ll be working with the White House, helping them with clemencies,” Kardashian explains, as a photo appears onscreen of her with Alice Johnson, the woman whose life sentence she personally persuaded the president to commute, in the Oval Office with Trump.

Clearly uncomfortable with the notion of aiding Trump’s image, Letterman then asks, “But do you feel that what is being done on behalf of sentencing reform now via this current administration in any way allows the balance of democracy back in a corridor of viability?”

It’s a terribly worded, nonsensical question that elicits the only logical response from his guest, who replies, “Well, I have no idea what you just said.”

After the laughter and applause dies down, Letterman tries another tack. “I’m grateful for what you’re doing, but it doesn’t make me feel any better about the current administration,” he says. But as she has done repeatedly over the past couple of years, Kardashian refuses to say one bad word about the man in the White House, only telling him, “I understand that.”

She will not even tell Letterman who she’s voting for in the presidential election, sitting in silence as he presses her with, “I know who I’m voting for.” Though the interview was taped before Joe Biden had locked up the Democratic nomination and before Kanye West officially threw his MAGA hat in the ring, the obvious implication is whoever has the best chance of beating Trump.

“Trust me, everyone called me and said, ‘Don’t you dare step foot in that White House or your reputation is done,’” Kardashian says, arguing that it was a small price to pay for saving the lives of people who would otherwise die in prison.

“But see, your good work is overwhelming,” Letterman admits. “It’s a positive force that diminishes what I consider to be unacceptable behavior by the president.”

Trust me, everyone called me and said, ‘Don’t you dare step foot in that White House or your reputation is done.’

Kim Kardashian West

Instead of agreeing that any such “unacceptable behavior” exists, Kardashian only says she is “extremely grateful” for the administration’s work on criminal justice reform and will “stay focused” on what she can accomplish.

“Why don’t I feel like that? I’m not as good a person as you, maybe?” Letterman asks in response, before realizing that he has perhaps reached a dead end and moves onto other topics. Their conversation culminates with a truly harrowing account of the 2016 Paris robbery during which Kardashian says she was sure she was going to die.

Throughout the hour, Letterman’s obvious affection for Kardashian is apparent. Ultimately, he tells her that she’s “come out on the right side of everything.” But he is also clearly distressed by her outright refusal to criticize Trump, who he has known for decades should never have been given the power of the presidency.

Months after their interview, Alice Johnson appeared as a featured speaker at the Republican National Convention. But while she profusely thanked the president for commuting her sentence, she notably declined to endorse him for a second term. Like Kardashian, Johnson told CNN’s Jake Tapper that she was “focused” on this narrow mission and clearly did not want to say anything that might bruise Trump’s ego.

As a fellow reality show star, Kardashian knows that Trump cares far more about being liked than he does about actually helping people so she wasn’t going to reveal even the slightest hint of disapproval. Letterman has become a world-class interviewer in his new longer format, but even he couldn’t get her to break.

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