In the closing weeks of the year, two of television’s most prominent late-night hosts used their stages to deliver an unusually pointed critique of former President Donald Trump — and to warn of what they described as mounting pressure on the press.

On a recent broadcast of “The Late Show,” Stephen Colbert addressed reports that a major network had settled a lawsuit Mr. Trump filed over the editing of a “60 Minutes” interview with a Democratic candidate. The network characterized the settlement as a business decision; Mr. Colbert called it troubling. “It is important to have a free press,” he told his audience, adding that journalists should not be required to pledge loyalty or seek approval before reporting unclassified information.

Across town, on “Jimmy Kimmel Live,” Jimmy Kimmel took aim at Mr. Trump’s fundraising tactics and his frequent social media posts attacking critics. The two hosts, though distinct in style, converged on a common theme: that political power and media independence are colliding in ways that merit public scrutiny.

The friction escalated after Mr. Trump posted a series of late-night messages criticizing Mr. Colbert by name, calling him untalented and suggesting that networks reconsider his future. The former president has long targeted television personalities who mock him, but his recent posts were unusually personal, arriving shortly after midnight on Christmas Eve.

In response, Mr. Colbert opened his show by reading excerpts from the posts and placing them in a broader context. He replayed clips of Mr. Trump confusing him with Mr. Kimmel during a public appearance at the Kennedy Center, then deadpanned: “I hosted those honors. Jimmy didn’t.” The audience laughed, but the underlying message was clear: the president’s grievances were less about accuracy than about irritation.

Mr. Kimmel’s monologue took a different tack. He focused on a series of campaign emails that he said were designed to create urgency among supporters, using phrases like “alert” and “brink of disaster” in bold type. One email included a small-print notice indicating that by checking a box, recipients would authorize an additional automatic donation. Mr. Kimmel argued that such tactics could confuse elderly donors. “What exactly are you fundraising for?” he asked, noting that Mr. Trump is constitutionally barred from seeking another term.

The allegations have also been amplified by commentators at the MeidasTouch Network, who have described the emails as deceptive. They argue that the formatting and language resemble high-pressure marketing schemes. The Trump campaign has denied wrongdoing and maintains that all solicitations comply with federal election law.

The dispute over media independence intensified when the Federal Communications Commission, led by Chairman Brendan Carr, discussed new policies regarding press credentials at the Pentagon. Critics, including Mr. Colbert, characterized the proposal — which would require journalists to pledge not to publish information that had not been explicitly cleared — as an infringement on press freedom. Supporters of the measure said it was necessary to protect national security and prevent leaks.

Meanwhile, speculation swirled around corporate decisions in the entertainment industry. CBS announced that “The Late Show” would conclude in 2026, describing the move as financially driven. The timing prompted questions because the network’s parent company was simultaneously seeking federal approval for a merger. Some commentators suggested that the settlement with Mr. Trump and the cancellation of a program that frequently criticized him were linked. The company has denied any connection.

The Writers Guild of America publicly urged the New York attorney general to examine the circumstances, citing concerns that business interests could influence editorial choices. Senator Elizabeth Warren, Democrat of Massachusetts, said the public “deserves transparency” about whether political pressure played a role.

For his part, Mr. Trump celebrated the cancellation on social media, writing that he “absolutely loved” seeing Mr. Colbert lose his show. He has framed criticism from late-night hosts as evidence of bias within legacy media institutions and has repeatedly accused networks of conspiring against him.

Yet the clash underscores a larger dynamic in American politics: the increasingly blurred boundary between governance and entertainment. Late-night television, once a relatively safe harbor for bipartisan humor, has become an arena where constitutional questions about free speech and executive influence are debated before studio audiences.

In recent broadcasts, both Mr. Colbert and Mr. Kimmel have argued that what may appear to be a feud between a politician and comedians is in fact a test of democratic norms. “It always starts small,” Mr. Colbert told viewers, warning against incremental concessions to authority. Mr. Kimmel, alternating between satire and pointed commentary, suggested that laughter can function as a form of oversight.

Whether audiences see the hosts as defenders of free expression or as partisan antagonists depends largely on their political allegiances. But the exchange has ensured that the relationship between political power and media independence remains in the spotlight — even if the stage is set with a desk, a band and a laugh track.

As the new year begins, the confrontation shows no sign of abating. Mr. Trump continues to post; the comedians continue to respond. And millions of viewers, tuning in for jokes, find themselves watching a deeper argument about the boundaries of criticism in a democracy.