When Donald Trump announced a new round of defamation lawsuits this week, the targets were familiar: major news organizations, late-night television, and critics he has long accused of conspiring against him. Less familiar was the response. Instead of cautious silence, one of those critics, Jimmy Kimmel, chose to confront the threat head-on—on live television.

Mr. Trump’s latest legal action, filed against CNN, accuses the network of defamation for commentary and reporting that, he says, damaged his reputation. The lawsuit follows a pattern that has become increasingly central to Mr. Trump’s post-presidency strategy: casting media criticism as not merely unfair or biased, but unlawful. In public statements, he has portrayed the suits as a defense of free speech and personal dignity. Critics counter that the cases are designed to intimidate journalists and commentators.

Complicating matters was a brief flurry of claims online suggesting that Mr. Kimmel’s show on ABC had been canceled—claims the network quickly denied. Mr. Trump seized on the confusion, mocking Mr. Kimmel’s ratings and talent in social media posts and suggesting that the host’s continued presence on the air reflected political favoritism rather than audience support.

On the next broadcast of Jimmy Kimmel Live!, the host responded directly. Rather than avoiding the lawsuit threat, Mr. Kimmel invited it into the open, treating Mr. Trump’s legal and rhetorical offensives as material for scrutiny rather than intimidation. The studio audience reacted with sustained applause, signaling a shift in how such threats are received in popular media.

Mr. Kimmel’s approach was notable for its structure. He did not simply ridicule Mr. Trump’s language or posture. Instead, he inverted the former president’s own talking points. When Mr. Trump attacked the host’s ratings, Mr. Kimmel countered with polling data from Mr. Trump’s presidency, noting that approval numbers—by Mr. Trump’s own standard—would have warranted dismissal. The comparison drew laughter, but it also underscored a broader argument: that the metrics Mr. Trump uses to judge others apply equally to himself.

The segment then widened its scope. Mr. Kimmel referenced Mr. Trump’s separate, multibillion-dollar lawsuit against The New York Times, questioning how a publication Mr. Trump frequently labels “failing” could simultaneously be expected to pay damages of such magnitude. The contradiction was left to stand without extended commentary. In the logic of late-night television, the point landed precisely because it was understated.

Legal experts note that defamation suits involving public figures face a high bar under American law, requiring proof of actual malice. While Mr. Trump has succeeded in drawing attention to his grievances, courts have historically been skeptical of claims that opinionated commentary constitutes defamation. Several of Mr. Trump’s previous suits have been dismissed or withdrawn.

What distinguished this episode was not the legal substance of the claims but the cultural response. Mr. Trump has long relied on the threat of litigation as a show of strength, a signal that critics should proceed cautiously. Mr. Kimmel’s decision to laugh at the threat—rather than hedge against it—suggested that the tactic may be losing its deterrent effect, at least in entertainment media.

The host also drew attention to the internal strain such conflicts place on political organizations. He described aides scrambling to reframe Mr. Trump’s statements as jokes or misunderstandings, only to be undermined by subsequent posts that reiterated the original attacks. The image presented was not of a coordinated legal strategy but of reactive escalation, driven by impulse as much as planning.

By the end of the segment, Mr. Trump’s lawsuits were portrayed less as disciplined legal campaigns than as expressions of grievance. The laughter in the studio was loud, but it was not merely dismissive. It reflected a recognition that the balance of intimidation had shifted. Where once the threat of being sued might have silenced a critic, it now served as fodder for critique.

For Mr. Trump, the confrontation highlighted a central tension of his public life: the desire to dominate the media narrative while remaining deeply engaged with it. For Mr. Kimmel, the moment reinforced the evolving role of late-night television—not simply as entertainment, but as a forum where power is tested through irony, facts, and audience judgment.

As legal proceedings move forward, the courts will determine the merits of Mr. Trump’s claims. But in the court of public attention, the exchange offered a clear lesson: threats that rely on fear lose force when met with transparency and humor.