Kimmel Trolls Trump for Shipping Kimberly Guilfoyle to ‘Farthest Country Possible’: “What a Family”

Late-night host Jimmy Kimmel was back at it again, doing what he loves most— trolling President-elect Donald Trump. Kimmel dove right into the latest Trump family drama, delivering a sharp commentary on the President-elect for shipping Kimberly Guilfoyle to Greece. The decision came after photos of Donald Trump Jr. having an intimate brunch with Palm Beach socialite Bettina Anderson went viral on social media, hinting that his engagement with Guilfoyle was in fact over after months of speculation.

Kimmel wasted no time on his Tuesday monologue, drawing attention to the timing of the announcement. “The First Boy [Don Jr] has not made an announcement about the status of his relationship with…Kimberly Guilfoyle, but something sure seems to be up,” the comedian began. “He [Donald] made her ambassador to one of the farthest countries possible,” Kimmel further quipped. The appointment came less than 24 hours after photos of Don Jr. and Anderson hit the media, walking hand in hand, as per the Daily Beast .

“What a family this is,” Kimmel remarked, tossing in another jab about Donald’s vast network of relatives who have held significant political positions despite not having any expertise in the same. Kimel continued, “[Donald] has more family members working at the White House than I have on this show right now.”

Guilfoyle and Don Jr. were once considered the ‘prom king and queen of MAGA land,’ with their relationship being a key fixture in Donald’s political scene. Engaged and often seen together on the campaign trail , Guilfoyle worked as a senior adviser to the Trump campaign. On her latest appointment, Don Jr. gushed on X , “I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.”

Sources close to the couple claim their romance has cooled, with Don Jr. allegedly spending more time with Anderson. The source also let slip one juicy tidbit: it was Anderson who concocted a plan to send Guilfoyle, out of the country. “Bettina wants Kim out of the area,” an insider recently told People magazine . “They waited for the election to pass but they didn’t want the split to get in the way of anything to hurt Donald in the election,” the source added. Another dead giveaway was Don Jr.’s daughter Kai Trump following Anderson on Instagram rather than Guilfoyle.

While an official announcement of a split is yet to come, Guilfoyle embraces her new diplomatic role with characteristic élan, pledging to represent the United States in Greece. Donald’s announcement praised Guilfoyle’s credentials as a person with “extensive experience and leadership in law, media, and politics.” For her part, Guilfoyle saluted the opportunity, citing the historical connection between Greek democratic values and America’s founding principles.