Why Donald Trump's Feud Against Late-Night Keeps Going Viral: Inside His Clash With Stephen Colbert

The feud between late-night television and President Donald Trump’s orbit has become so familiar that it now functions as its own kind of media storyline.

The latest example came this week when White House Communications Director Steven Cheung unleashed a viral tirade against The Late Show host Stephen Colbert.

Cheung’s attack — posted on X alongside an article about Colbert’s final season before the show ends May 21 — called the host “a sad and pathetic excuse for a human being” and predicted that he would soon be forgotten.

The outburst quickly circulated online, drawing attention not just to the insult itself but to a recurring dynamic: political figures responding publicly to late-night comedians.

Media analysts say ridicule often hits political leaders differently than traditional criticism.

“Political leaders tend to react very differently to ridicule than to policy criticism,” said Kaivan Shroff, media and cultural analyst and founder of the Yale School of Management Social Media Lab.

“A policy argument can get lost or obfuscated in the details,” he explained. “A joke that resonates or goes viral, on the other hand, can shrink a public figure’s stature or authority on a subject in seconds.”

That power, Shroff noted, helps explain why comedians become political targets.

“That’s why comedians so often end up treated like political adversaries and can become the first targets of authoritarian regimes — because they strike at the very legitimacy of those they mock,” he said.

Cheung’s remarks also reflect a strategy the Trump political operation has used repeatedly: responding aggressively to critics in the entertainment world.

The communications chief has previously lashed out at other late-night hosts, including Jimmy Kimmel, often using social media to deliver personal insults aimed at discrediting their commentary.

But this approach can backfire.

“Usually, the politicians engaging with the comedians is a losing proposition,” Shroff added. “Leaders are supposed to be held to a higher standard and getting into the mud with entertainers can appear unfocused and unserious.”The political attacks end up drawing more attention to a comedian, Shroff said, often increasing their influence instead of diminishing it.

“This White House is always eager to punch and punch back, so their strategy is always to state their position and retort as aggressively as possible to appear strong,” he continued. “This may work for certain parts of their base, but if anything, that kind of reaction often gives even more power to the comedy or satire that irked them in the first place.”