The makeup mogul, 39, joined the TV personality on the newest season of Netflix's My Next Guest Needs No Introduction, and the 73-year-old confronted the reality star on her criminal justice reform work with the White House.
"Trust me, everyone called me and said, 'Don't you dare step foot in that White House or your reputation is done,'" the KUWTK star shared with Letterman, according to the Daily Beast. "And I said, 'I have to step foot in there or these people's lives don't have a chance.'"
She added, "Hopefully, for the next multiple administrations, I'll be working with the White House, helping them with clemencies."
"But see, your good work is overwhelming," the comedian replied. "It's a positive force that diminishes what I consider to be unacceptable behavior by the President." While the mother of four wouldn't comment on Trump's "unacceptable behavior," she continued to answer questions about their relations and work.
"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?" Letterman asked, leading the Skims founder to respond: "Well, I have no idea what you just said."
"I'm grateful for what you're doing, but it doesn't make me feel any better about the current administration," the host noted, to which Kardashian replied, "I understand that." The socialite also said she knows who she is voting for in the 2020 presidential election but wouldn't say who.
During the interview, the fashion mogul said she is "extremely grateful" for the chance to work with the administration as she is determined to "stay focused" on her goals for change. Kardashian previously worked with Trump in 2018 to grant clemency to Alice Marie Johnson after she spent 20 years behind bars of her life sentence.
Kardashian's work for change is far from over. She released her new documentary Kim Kardashian West: The Justice Project on April 5, which took viewers through the process of her criminal justice reform work. "What I wanted to do with this documentary is take people along with my journey, how I started off with Alice, non-violent drug offender, to going into people that have done some really serious crimes," she told CBS This Morning co-host Gayle King in an interview at the time. "Realizing that their life doesn't have to be thrown away, that they do deserve a second chance.
"Once I really got to know Alice, and realizing that there are thousands more Alices, I couldn't just sit back and not try to make a difference and not try to change," the businesswoman added. When asked if she cares if people judge her from the way she grew up on reality TV, Kardashian candidly responded: "I can honestly say that I don't care if someone views me as this way or that way or however. I just know what I'm doing and I'm focused on that."
Kardashian has since gotten three women who were facing lengthy sentences for nonviolent crimes commuted by the President. Trump's order has granted clemency to 11 convicted people. When previously asked during an interview with Stephanie Gomulka why the successful mother cares so much about this topic, Kardashian explained: "I have kids. I'm raising two Black sons, that, if you look at the statistics of who ends up behind bars, it scares me to know the system is so broken and so unfair. So anything that I can try to do to have a better life for them, is why I love doing what I’m doing."
The Letterman interview was taped before Joe Biden officially secured the Democratic nomination and before husband Kanye West entered into the race. West — who shares daughters North, 7, Chicago, 2, and sons Saint, 4, and Psalm, 1, with Kardashian — is on the ballot in 12 states as the Birthday Party/Independent Party candidate. In a recently released campaign ad — just three weeks prior to the election — the "Gold Digger" singer vowed to "restore the nation's commitment to faith" and "build a stronger country by building stronger families."
Season three of My Next Guest Needs No Introduction will be released on Netflix on Wednesday, October 21.