Former Obama envoy slams Trump’s AI dumpster video following Colbert’s Late Show finale

Colbert signed off with an emotional farewell, calling the show a "joy machine" in a speech
PUBLISHED MAY 24, 2026
Richard Stengel at The Ziegfeld Ballroom in New York City. (Image Source: Getty Images | Photo by Slaven Vlasic)
Richard Stengel at The Ziegfeld Ballroom in New York City. (Image Source: Getty Images | Photo by Slaven Vlasic)

Former Under Secretary of State Richard Stengel blasted President Donald Trump after he posted an AI-generated video of him throwing late-night host Stephen Colbert into a dumpster, terming his rant a sign of a "weak" and "insecure" man.

Celebrity Sightings In New York City - May 21, 2026
Stephen Colbert is seen at an after-party for the finale of
Celebrity Sightings In New York City - May 21, 2026 Stephen Colbert is seen at an after-party for the finale of "The Late Show with Stephen Colbert" in New York City. (Image Source: Getty Images | Photo by XNY/Star Max/GC Images)

Stengel, who served under the Obama administration, lauded Colbert's final show for not mentioning Trump "even once" and characterized it as a "joyous" affair. In contrast, he added that Trump went on a rant in which he called Colbert a "total jerk".



"Who is the strong man and who is the weak one? Who is the secure man, and who is the insecure one? Which one do you want your kids to be like?" he concluded. Colbert took over "The Late Show" from David Letterman in 2015.

President Donald Trump speaks during a visit to the Fort Bragg U.S. Army base on February 13, 2026 (Photo by Nathan Howard/Getty Images)
President Donald Trump speaks during a visit to the Fort Bragg U.S. Army base on February 13, 2026 (Photo by Nathan Howard/Getty Images)

Stengel's post highlights the difference between the dignified conclusion of a late-night show after 11 years and Trump's aggressive social media response. His comments also reveal the fault lines between Trump and his critics, and how his way of dealing with them can often be vengeful, immature, and fundamentally beneath the office.

The video was not Trump's only attack against Colbert. He wrote that Colbert’s firing was the “beginning of the end” for "untalented, nasty, highly overpaid, not funny, and very poorly rated" late-night television hosts. He threatened that others, "of even less talent", will soon be following Colbert's suit.



The president's list of feuds with late-night show hosts runs long. He called for NBC's Seth Meyers to be axed in 2025 after he consistently ridiculed him in his monologues, accusing Meyers of suffering from "Trump Derangement Syndrome (TDS)".



ABC's Jimmy Kimmel is another host with a target on his back. Trump's long-running clash with Kimmel reached its nadir earlier this year, after he called for Kimmel’s firing when he quipped that First Lady Melania Trump had a “glow like an expectant widow,” a day before an alleged assassination attempt on Trump at the White House Correspondents' Dinner.

Colbert's bad blood with Trump might have played a role in his firing by CBS, according to many, including Colbert. He told The New York Times that something changed after CBS called him two years before the cancellation, and conveyed they wanted him to be "signed for a long time".



Things took a turn after he criticized CBS's parent company, Paramount, for settling a lawsuit with Trump over the editing of a "60 Minutes" interview with Kamala Harris, calling it a "big fat bribe". The ending's announcement came at a time when Paramount was seeking to merge with Skydance Media, a move that would have required the federal government's stamp of approval.

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