Times Jimmy Kimmel Brutally Slammed The Trump Family

Known for his critical stance on former President Donald Trump, Comedian Jimmy Kimmel has found additional ammunition in the New York civil fraud trial involving the Trump family. On November 13, 2023, Kimmel celebrated his 56th birthday with a standup routine targeting the Trumps, whom he labeled a "very dumb crime family." His jokes revolved around the Trump family's alleged strategy of consistently denying knowledge of the fraudulent practices for which they were found liable.

Kimmel also dubbed them the "Gambozos," merging the infamous Gambino crime family and the slang "bozo." His routine humorously featured an interview skit, with talk show personality Guillermo Rodriguez as the interviewer. When Rodriguez asked what appeared to be an AI-generated Trump to identify his two sons, he responded, "These are people that are very, very disturbed." This isn't nearly the first time Jimmy Kimmel has aimed at the Trump family. Over his decades-long career, the talk show host has frequently criticized various Trump family members. Here are five of Jimmy Kimmel's most brutal digs at the Trump family.

Melania Trump, often portrayed as the long-suffering matriarch of the Trump family, has not been spared by Jimmy Kimmel's comedic jabs. A notable instance followed a November 10, 2023, report by The Washington Post. The article featured an interview with Melania's former advisor, Stephanie Winston Wolkoff, who revealed that Melania delayed moving to the White House until a new toilet was installed. In response, Kimmel joked that she probably wanted to ensure it was "large enough to flush herself down."

On Melania's 52nd birthday in 2020, Kimmel couldn't resist a playful dig, joking that Trump sent her a birthday email beginning with, "Dear supporter." Kimmel also played on words after learning that Melania was discovered by photographer Stane Jerko, commenting that she "eventually married a much bigger Jerko." The comedian has consistently poked fun at the supposed signs of Donald Trump and Melania's split. On October 26, 2020, he made a tongue-in-cheek comment about her alleged body double, suggesting that such a smile would have been a reality for Melania had she married someone else.

Jimmy Kimmel's playful roasting of the Trump family inevitably includes former First Daughter Ivanka Trump. In 2017, when Ivanka received an office in the West Wing, Kimmel remarked that she would bring her "20 years of foreign and domestic policy experience that she gained selling sandals to Nordstrom" (via Business Insider). He also humorously suggested that Ivanka was positioned close to her father to prevent him from deploying nuclear weapons (via Yahoo Finance).

Kimmel didn't shy away from commenting on how Ivanka Trump almost lost her job as a White House advisor. He sourced material from the book, "Confidence Man" by Maggie Haberman, which stated that Trump planned to fire Ivanka and her husband, Jared Kushner, via a tweet. Kimmel jested that Ivanka was saved by a KFC chicken thrown across the room to distract her father. On February 15, 2023, when Donald Trump expressed a desire to reinstate firing squads, Kimmel's response was expectedly sharp-witted: "If Trump executes all the criminals, who's going to send him a Father's Day card? Friends of Ivanka?"