Kimberly Guilfoyle Caught Begging Trump Donor to Pay Her $100K Amex Bill | Kyle MacLachlan

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From the most trusted journalists at Comedy Central, it's America's only source for news. This is The Daily Show with your host, Michael Kosta.

Michael Kosta (1:33)

One Trump donor finds that a bribe doesn't go as far as it used to. There's a new problem with the border wall, and Kimberly Guilfoyle's latest scandal will have you saying, Oh, right, her. And later on, the great Kyle MacLachlan will be here. But first, let's get into another edition of The Worst Wing.

What a bunch of losers.

Let's start with the US ambassador to Greece, Kimberly Guilfoyle. You might remember her as Don Jr.'s former fiancé. Sadly, the relationship fell apart after they got to know each other. Or you might remember her from the Trump campaign, where she gave this epic speech.

SPEAKER_1 (2:24)

Ladies and gentlemen, leaders and fighters for freedom and liberty and the American dream, the best is yet to come.

Michael Kosta (2:38)

Sadly, her sign language interpreter died of exhaustion. Of course, before Guilfoyle broke the sound barrier, she reportedly made history as the only woman to get fired from Fox News for sexual harassment. Hey, you go, girl. No, specifically to HR. Go to HR immediately.

With such a stellar resume, it's no surprise that she was nominated to be Trump's ambassador to Greece, a critical role in overseeing America's big fat weddings. And so, it's reassuring to know our diplomatic core is staffed with such paragons of integrity and above all, dignity.

SPEAKER_10 (3:19)

US ambassador to Greece and Donald Trump Jr.'s former fiance, Kimberly Guilfoyle, pushed a Trump donor to send her $100,000 to pay her American Express bill last year.

SPEAKER_3 (3:29)

Honey, please, I need you to get this done for me today.

SPEAKER_10 (3:32)

Adding a prayer hands emoji and a PDF with bill payment instructions from American Express.

Michael Kosta (3:37)

Wow, that was not subtle. Um, usually it's meet me in the parking lot with a suitcase full of bills, but Guilfoyle was like, here is a PDF with instructions for how to send me a bribe. Please send the bribe today, honey. Man, if the Justice Department still existed, you'd be in so much trouble. And damn, a $100,000 credit card bill. Ah, now her current job makes sense. Hmm, we need a new ambassador who really understands Greece. Kimberly, you're deep in debt. You'd be perfect.

Okay.

But yes, Kimberly Guilfoyle, seen here demonstrating the size of her debt, wanted this guy to pay off her Amex card. But the question is, well, what does he get out of it?

SPEAKER_5 (4:32)

Guilfoyle told him if he paid her Amex bill, quote, I will be your Trump ride or die forever and ever.

Michael Kosta (4:39)

Oh, Trump's ride or die. That's a good deal. Everyone knows there's no closer relationship than that of a man and his son's incredibly loud ex-fiance.

Now, maybe you're thinking, is it possible that Kimberly Guilfoyle was too stupid to understand that this was wrong? And that is a reasonable thought. But judging by her other texts, she knew.

SPEAKER_5 (5:02)

Guilfoyle began to express concerns about their dealings becoming public and sent him this message on Signal. Eric, I really wish you would stop papering all these things. It's really dangerous and not helpful to you or me, while you could simply just call me on Signal. She added, what a nightmare. You're literally cost me my ambassadorship. Stop writing.

Michael Kosta (5:22)

Oh, real criminal mastermind we got here. She left a paper trail about not leaving a paper trail. Didn't help that she named the group chat Paper Trail, parentheses, Crimes.

She had a point, though. Why wouldn't this guy just call her on the phone?