Former Obama envoy slams Trump’s AI dumpster video following Colbert’s Late Show finale
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.
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".
This is an official government account in a democracy.
— Mehdi Hasan (@mehdirhasan) May 23, 2026
This is what Orbanism looks like. The president bragging, via AI video, that he forced a comedian who mocked him off the air and ‘into the trash’. https://t.co/NHWnO3ooMv
"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.
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.
Stephen Colbert has a talent for making people laugh and encouraging them to stay curious, stay engaged, and stay hopeful about the world around them.@StephenAtHome: Thank you for your voice, your creativity, and so many memorable conversations over the years. Cheers to you. pic.twitter.com/etK8Izb7NY
— Kamala Harris (@KamalaHarris) May 21, 2026
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)".
Congratulations to @StephenAtHome on over a decade of The Late Show with Stephen Colbert.
— Senator Alex Padilla (@SenAlexPadilla) May 22, 2026
Like so many, I looked forward to tuning into the Late Show for a fresh take on the day's news, a good laugh, and genuinely meaningful commentary.
A source of joy when the nation… pic.twitter.com/8qtCAJcJRf
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".
Congratulations to Stephen Colbert on an incredible run with The Late Show. I really enjoyed appearing on your predecessor show the Colbert Report CBS and late night television are going to sorely miss your wit, your kindness, and your commitment to making Americans laugh every… pic.twitter.com/glRwD1nlUI
— Governor Jared Polis (@GovofCO) May 22, 2026
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.