Donald J. Trump has clashed with late–night comedians for nearly a decade. But his simmering feud with Jimmy Kimmel and Stephen Colbert has now hardened into something closer to a sustained, two–front media war — one that blends television, politics and personal grievance, and that, according to critics, reveals as much about Trump’s approach to power as it does about the role of comedy in American public life.

In a recent online video that quickly circulated on social media, a liberal commentator stitched together segments from Kimmel’s ABC monologue and Colbert’s CBS “Late Show,” framing them as part of a coordinated effort to “expose” what he called the former president’s “dirty secrets” — from his handling of a shooting near the White House to his resistance to releasing files related to Jeffrey Epstein, to his habit of monetizing the presidency through merchandise and crypto ventures.

The piece opened with a pointed image: Thanksgiving, a holiday Trump has often used to unleash late–night social media tirades, passing in unusual quiet. “Donald Trump is panicking and he has gone mute,” the narrator declared, noting that the former president had not yet posted his customary grievances. That silence became a narrative fulcrum: a man who built his political brand on constant, unfiltered communication suddenly framed as rattled and unsure.

From there, the video moved quickly through a collage of late–night jokes and political developments. One thread focused on Trump’s social media boast that he was on a lengthy call with President Vladimir V. Putin of Russia — a boast Kimmel and Colbert seized on as emblematic of Trump’s need for attention. “Why are you posting about a phone call while you’re on the call?” one quipped, likening Putin to a prankster who calls simply for amusement, with Trump cast as the perennial mark.

Another segment highlighted Trump’s claim, made in a friendly television interview, that no other president had “ended a war,” while he insisted that he had ended “eight of them.” Colbert treated the assertion less as a policy statement than as a window into Trump’s indifference to fact, remarking that it illustrated the risks of “never learning anything” because it might “damage your self–esteem.”

But the commentary that wrapped around the jokes pressed a darker argument. The narrator repeatedly referred to the “Trump regime,” accusing it of mishandling a high–profile shooting in Washington, and of having granted asylum earlier in the year to the alleged gunman, an Afghan who had previously worked with U.S. forces. Citing televised briefings and cable reports, he portrayed a government eager to blame lax vetting while, in his telling, sidestepping its own role in bringing the man into the country. Those claims, presented in highly charged language, could not be independently verified within the video itself.

The same piece wove in another controversy: a lopsided House vote to move toward releasing long–sealed Epstein–related records. Late–night hosts, the narrator noted, seized on the one “no” vote as a punchline, speculating — in jest — that Trump himself might fear appearing in the files. Kimmel dramatized the moment with a riddle about a figure who “rides a golf cart in the afternoon and is totally in the Epstein files,” a line that drew big laughs but underscored how deeply the Epstein case has entered the realm of political insinuation.

On air, Colbert and Kimmel cast their relationship as something stronger than professional collegiality. During the 2023 writers’ strike, they joined three other hosts in launching a limited–run podcast, “Strike Force Five,” to raise money for their idle staff members. That experience, Colbert later said, turned the late–night rivals into “podcast brothers.” In the new video, that phrase is treated almost like a pact: a promise that when Trump targets one host, the other will answer.

That dynamic played out around the Academy Awards in 2024, when Kimmel, hosting the ceremony, read one of Trump’s social media attacks about his performance and responded in real time, joking that it was past the former president’s “jail time.” Trump continued to fume online in the weeks that followed; Colbert, in turn, used his own program to mock the outburst, portraying Trump as consumed by late–night television at the expense of governing.

What the commentator behind the latest video argues is that Trump’s response has not been limited to insults. He points to a tangle of lawsuits, regulatory pressures and corporate decisions — including a settlement paid to Trump by a major media conglomerate — as evidence of a broader attempt to chill criticism from entertainers who command large audiences. In this telling, late–night monologues are not merely jokes but acts of resistance against an increasingly authoritarian political figure.

At the same time, the video dwells on Trump’s commercial ventures, including a line of branded watches promoted on conservative cable networks and what it describes as substantial profits from cryptocurrency. Kimmel joked that Trump, who is rarely seen wearing a watch, was selling products of dubious quality to loyal followers. The narrator, more pointedly, suggested that this was part of a pattern: leveraging the aura of the presidency for private gain.

The piece ends on a note of unvarnished admiration for the comedians it features. “That’s not just comedy,” the commentator says over a montage of applause and laughter. “That’s courage.” He frames the Kimmel–Colbert partnership as a model for how media figures might respond when political leaders seek to punish or silence criticism, arguing that their willingness to “look him in the eye” and push back reflects a broader public desire not to “bow down to a president who can’t take a joke.”

For now, the conflict remains asymmetrical: two network hosts and a constellation of online critics on one side, and on the other a former president with a fervent base, deep cultural reach and, should he return to office, formal powers that extend far beyond the programming choices of late–night television. But the video’s underlying suggestion is that the battleground has shifted. In an era when jokes double as political argument and ratings can rival turnout, late–night stages have become yet another arena where the fight over Trump’s legacy — and his future — plays out, punchline by punchline.