On “The Late Show” Wednesday night, host Stephen Colbert had on former Trump Administration staffer and recent “Big Brother” participant Omarosa Manigault-Newman to discuss anything and everything Colbert could think to ask her about her time working for the president in a 20-minute interview.
The version of the interview that aired on CBS ran just under ten minutes.
After a warm welcome and small talk, where Colbert introduced Omarosa as someone who “went from the White House to the ‘Big Brother’ house and managed to make it out of both of them alive,” the host asked about the viral clip of Omarosa telling one of her “Big Brother” housemates regarding Trump that “it’s going to not be okay.”
Omarosa laughed at the clip, saying it was actually the first time she’d seen it.
“Was that a joke? Because you’re laughing about it,” Colbert said. “But he’s chilled, and I’m chilled by watching it because you know Donald Trump, you were in the White House, you were close to the events that were happening. What do you mean it’s not going to be OK?”
Initially, Omarosa didn’t directly answer the question, saying that the clip was out of context and that it was part of “a bigger discussion…about immigration and roundups.” But after continued prying from Colbert, she said that “we’ll have to wait and see.”
That back-and-forth kicked off a long sequence of similar interactions in which Colbert tried his hardest to get Omarosa to spill some beans and also give some greater context for what in the world is going on in the Trump administration, but for the most part, she hedged her answers. She was willing to discuss her disapproval of Trump’s Twitter habit, but avoided expressing displeasure with his political platforms.
She did, however, explain why it’s so hard for her to speak ill of Trump.
“Look, Donald Trump was my friend for 15 years,” Omarosa said.
“Watching him in this position has caused me to be excited sometimes and sometimes be very, very concerned. And I think if you woke up and your best friend was president tomorrow, you would have that same range of emotions.”
Colbert did not agree with that assertion.
“If my best friend was president tomorrow, I’d feel better,” Colbert said, triggering cheers from the audience and laughter from Omarosa. “Because she is way smarter than I am.”
Colbert asked Omarosa about probably the biggest news item from the Trump White House today, which was the resignation of White House Communication Director Hope Hicks — Omarosa’s old boss.
Hicks’ resignation came after she admitted to investigators that she had lied on Trump’s behalf — though the details on what exactly Hicks had lied about are not publicly known. That led Colbert to ask Omarosa if she knew what the lies were, prompting another laugh.
“I would suspect the first big one would be about crowd size,” Omarosa joked, referring to the administration’s claim that Trump’s inauguration drew the biggest crowd ever for a presidential inauguration.
“But I don’t really wanna go into it,” she continued, laughing again and drawing pleas from the audience.
“No please, let’s go into it,” Colbert replied, to cheers. “The people wanna know! You worked in the office of communications, let’s communicate how big the crowd was.”
At that, she gave in a little: “I got to attend the inauguration of Bill Clinton, Bush, Obama, and when we got to the Trump inauguration and they said this was the largest crowd size, I’m like, man, I’ve been to a lot of inaugurations and this isn’t the biggest crowd size. But I didn’t wanna be the one to break it to him. I didn’t wanna be that person!”
Late in the interview, Colbert listed off a bunch of Trump’s worst hits while she was working for him either during the campaign or in office, and Omarosa categorized all of them as either “awful” or “unacceptable.” Colbert reminded her that she stuck around through all of them.
“I don’t work for him, nor do I regret trying to be a voice of reason at the table and try to be the change,” she said.
Colbert then asked for further context for her comment about leaving the White House feeling like she’d been “freed from a plantation.”
“You know, the White House that I worked in, that Trump administration was — it was troubling and it was very difficult,” she told Colbert. “And my analogy of it being a plantation, meaning an ecosystem where people feel oppressed, is pretty clear. When you aren’t allowed to do the job that you were brought to do, to help be a change agent, to help be the liaison for communities that needed that assistance, that’s where that oppression comes from. And that’s what that analogy meant.”