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The White House Correspondents’ Association (WHCA) is surely hoping that Donald Trump will take a more diplomatic tone later this month when he makes his first appearance as president at the organization’s glitzy dinner in Washington DC, an annual event meant to honor and celebrate journalists and press freedom.

On Monday, Trump threatened to imprison a journalist if they refused to reveal the source of information that a second US airman was still missing after being shot down by Iran last Friday, which he claimed put the service member at risk.

“The person who did the story will go to jail if he doesn’t say,” Trump told a packed room of White House reporters, without specifying which reporter and which outlet he was referring to. The comment shocked watchdogs even at a time when the White House has become increasingly hostile to the media.

While some journalists and news organizations have long questioned the optics of the press mingling with the administration officials they cover, those questions have only grown louder after Trump’s threats and actions. In the first 14 months of his second term, Trump’s government has overseen a multi-pronged effort seemingly aimed at curbing news organizations that have been deemed hostile to his administration, threatening (and in some cases filing) lawsuits against media companies, cutting off access at the Pentagon by creating onerous new regulations, and even raiding the home of a Washington Post reporter.

Trump has avoided the dinner since his political ascendancy a decade ago. He last attended in 2015, when Barack Obama was still in the White House. In 2011, he appeared to be deeply angered when Obama and comedian Seth Meyers made jokes at his expense.

His return to the event has reignited discussions about the optics and utility of the event, which is nominally focused on raising money for journalism scholarships but has also been dubbed “Nerd Prom” – the biggest, most glamorous night of the year for the unglamorous scribes who cover the White House.

A veteran White House correspondent said some newsrooms were “wrestling” with whether to attend. “Last year was bad. This year is worse,” said the correspondent, who was not authorized to comment. “I understand it’s customary to invite the president, but we’ve never had a president like this before. It’s not about party affiliation. It’s not even about policy. It’s about the war he and his administration have conducted on the press and the first amendment and our ability to do our job.”

The news organization HuffPost announced on Monday afternoon that it would not attend the dinner, despite regularly doing so in the past.

“Donald Trump’s second term is an affront to the free press,” HuffPost’s editor-in-chief, Whitney Snyder, told the Guardian. “He has weaponized the FCC [the US media regulator], punished publications for exercising their first amendment rights, threatened to jail journalists and used lawsuits as a tool of intimidation – and that’s far from a comprehensive list. We refuse to celebrate journalism and share laughs with a ruler who holds such a dreadful record.”

Officially, the WHCA is pleased that Trump will be attending the dinner. “We’re happy the president has accepted our invitation and look forward to hosting him,” Weijia Jiang, a CBS News White House correspondent, said in a statement last month. (Representatives for the WHCA did not respond to a request for comment.)

In a town that craves a return to normality, some White House correspondents view Trump’s attendance at the dinner as a good thing, an indication that he was still willing to mingle with what he has deemed the opposition. Despite his regular broadsides against the media, Trump has taken dozens of calls from reporters since launching an attack against Iran, though the quick calls rarely generate much in the way of news and are often contradictory.

“I don’t think that letting him have an open microphone at the dinner is the complete disaster that some people think it’s going to be,” said a second veteran White House correspondent who requested anonymity because they were not authorized to comment. “He’s an entertainer, and I think he will probably go into it knowing who his audience is. I think he knows he’s not going to get the applause if he gets up there and starts telling us how much we all suck.”

The correspondent said he was most concerned about the logistical impacts of the president’s attendance and the Secret Service screening that comes with it: “It will turn leaving at the end of the dinner into a security circus.”

Jim Acosta, the former CNN anchor and now an independent journalist, said he considered getting a table this year until he found out that Trump was attending.

“What else is he going to do but show up and spike the football on news organizations that he has put over a barrel?” he said in an interview. “I don’t understand for the life of me why these news organizations go along with it. This is a moment, in my view, to stand up to this guy and say, ‘We’re not good with this.’”

The New York Times has long stayed away from the dinner, viewing its attendance as contributing to an unhelpful perception of coziness between the press and the administration. That policy has been fully vindicated by this year’s dynamic, argued Peter Baker, chief White House correspondent for the newspaper.

“This is exactly the kind of scenario that our editors decided a long time ago would be untenable,” he told the Guardian. “We are now hosting a dinner with a president who calls us ‘enemies of the people’, who is suing several of our organizations, who is using the power of government through the FCC to put pressure on other organizations. How this makes any sense is beyond me.”

This year, the WHCA won’t have to worry about the prospect of a comedian embarrassing the Trump administration, as Michelle Wolf did in 2018 when she roasted the then press secretary, Sarah Huckabee Sanders. Instead, the night’s entertainment will come from “famed mentalist” Oz Pearlman, who appeared on Fox Business Network this week and seemed giddy that Trump will be attending. “Make no mistake,” he said, “I have been training for 30 years for this moment to get inside the mind of somebody who says he is unreadable.”

As usual, news organizations are jockeying to invite cabinet members and elected representatives to sit at their tables, including some who have been particularly vocal in their criticism of the press. Among other administration officials, CBS News – now led by the heterodox commentator Bari Weiss – has invited the reliable media-basher Pete Hegseth, the defense secretary, a source with knowledge of the situation confirmed – though it is unclear if he will show up. CBS has also invited elected officials from both parties. (The media newsletter Breaker first reported Hegseth’s invitation.)

A CNN spokesperson declined to name the network’s guests, but said it has invited representatives of both parties as usual. (The Guardian’s table at the dinner will include leaders from press freedom organizations as well as Georgia Fort, the independent journalist arrested after covering a church protest in Minnesota in January.)

Some journalists attending the dinner may be wearing pocket squares or pins touting the importance of the first amendment, a quiet protest against the president’s anti-press rhetoric, as part of a campaign by the Reporters Committee for Freedom of the Press. But, Acosta asked skeptically: “What’s the point of a lapel pin when Donald Trump is shredding the constitution?”