Stephen Colbert Uses 'Late Show' Emmy Win To Epically Troll Trump's 'The Apprentice' Gripe

MAGA Republican President Donald Trump has a long history of sore losing. He notoriously cheats at golf and carries grudges every time he's bested in court or in the court of public opinion.

During a 2016 presidential debate, former Democratic Secretary of State Hillary Clinton brought up how Trump claimed Emmy voting was rigged when The Apprentice failed to win an award after two nominations.

Secretary Clinton said:

"There was even a time when [Trump] didn’t get an Emmy for his TV program … and he started tweeting that the Emmys were rigged against him."

In response, then candidate Trump griped:

"Should have gotten it."

The man lacks the maturity to accept his many failures in business, in life, and now in politics without lying about the loss or cheating to try to win. Trump's Big Lie after losing handily to Democratic candidate Joe Biden in 2020 and the insurrection he and his cronies incited on January 6, 2021 to try to overturn his loss, taught the world the lengths he'd go to protect his fragile ego.

Trump also lacks the maturity to see any of the many people he holds grudges against succeed.

Just look at the fool he continues to make of himself and all of his allies in his desperation to get a Nobel Peace Prize because Democratic President Barack Obama has one.

Sunday dealt another blow to Trump's fragile ego when The 2025 Emmy Awards were broadcast. Trump may not have tuned in, but he was undoubtedly unhappy with some of the winners and their acceptance speeches.

The Late Show With Stephen Colbert won best talk series for the first time, beating Jimmy Kimmel Live! and The Daily Show.

Colbert has been a frequent critic of Trump, his administration, and his cronies. The Late Show host has also shone a spotlight on Trump's relationship with the best buddy Trump wishes everyone would forget, Jeffrey Epstein.

On Tuesday, Colbert began his first monologue since the Emmys by saying:

"Ladies and gentlemen, welcome one and all. Welcome to The Late Show. I’m your host, Stephen Colbert. I’m sorry. I meant to say welcome to the Emmy Award-winning Late Show."

"On Sunday night we won our first Emmy for outstanding talk series. Man, I'm telling you, we should have gotten cancelled years ago."

After acknowledging the staff and crew behind the show's success, Colbert quipped while holding the golden statuette:

"Speaking of Emmys, Donald Trump doesn’t have one."

Hopefully the staff at Windsor Castle, where Trump reportedly spent the night during his state visit to the United Kingdom, knows how to get ketchup off walls.

You can see Colbert's riff on Trump here.

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People congratulated the show on their win and loved Colbert rubbing his Emmy in Trump's face.

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Colbert and his team received a standing ovation on Sunday as they took the Emmy's stage to accept their award.

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The Late Show with Stephen Colbert and the show's host have received a lot of industry support in recent months after CBS announced in July that the show would end in May 2026 for "financial reasons." Critics speculated that the motive was financial, but not for the reasons CBS cited.

Trump had recently received a $16 million payout for a frivolous, baseless lawsuit from CBS parent company Paramount. At the same time, the company needed approval from Trump's FCC for a planned deal with Skydance Media.

Paramount had joined numerous private law firms, corporations, and educational institutions to make payouts and undisclosed settlements or broker undisclosed agreements with Trump in order to continue business as usual without sanctions or punitive actions from the Trump administration after lawsuits filed or threats issued by Trump.

Colbert's criticism of the bribe was cited by many as contributing to the decision to kill his show, or possibly even part of Paramount's settlement with Trump—especially after Trump gloated on social media after the cancelation was announced.