Trump Keeps Losing in Court, Yet His War on the US Press Rolls On Regardless

Losing the battle, winning the war?

Donald Trump has spent the past few years racking up an impressive collection of legal defeats against American media organisations. You would think that being repeatedly told 'no' by federal judges might cool his enthusiasm for suing newspapers. You would be wrong.

The courtroom losses keep piling up. The pressure on the press, somehow, keeps intensifying. It is a peculiar sort of strategy: lose the lawsuit, win the chilling effect.

The latest courtroom flop

On 13 April 2026, Judge Darrin Gayles tossed out Trump's eye-watering 10 billion dollar defamation suit against The Wall Street Journal, brought over its reporting on a birthday note allegedly sent to Jeffrey Epstein. The dismissal was without prejudice, meaning Trump's lawyers can polish up the complaint and try again, but for now it is a clear loss.

It joins a growing pile. The 2022 suit against CNN over its election-rigging coverage was binned in 2023 by Judge Raag Singhal and upheld on appeal. Judge Randolph Moss ruled on 31 March 2026 that Trump's executive order defunding NPR and PBS was unconstitutional. The Pentagon's restrictive press-access rules have been struck down as unconstitutional twice in the past month alone.

That is not a winning streak. That is a man wandering into a courtroom with a banana and being surprised it is not a sword.

So why does anyone still flinch?

Because the lawsuit is not really the point. The point is the cost, the inconvenience, the regulatory leverage, and the very loud message sent to every newsroom watching from the sidelines.

Look at ABC. Rather than face a defamation case stemming from on-air remarks by George Stephanopoulos, the network agreed to pay 15 million dollars to Trump's future presidential library. Was the case winnable? Plenty of legal observers thought so. Did ABC fight it anyway? It did not. That is the whole game in a nutshell.

The FCC enters, stage right

If you cannot beat the press in court, you can always lean on the regulators. Enter Brendan Carr, the FCC chair, who has taken to his role with the energy of a man who has just discovered a new toy.

After Jimmy Kimmel made an 'expectant widow' joke about Melania Trump in April 2026, Carr's FCC reportedly ordered Disney to file early licence renewals for ABC stations. The signal to broadcasters could not be clearer: cross the administration and your paperwork suddenly becomes very interesting to the federal government.

Then there is the Paramount saga. CBS's parent company settled with Trump for a reported 16 million dollars over an editing dispute on 60 Minutes. Shortly afterwards, the FCC waved through the 8.4 billion dollar Paramount-Skydance merger. Make of that what you will. Stephen Colbert certainly did, calling the settlement a 'big fat bribe' on The Late Show. Paramount then cancelled his programme. Funny how these things work out.

The body count beyond the courtroom

The lawsuits are only the visible tip of a much larger iceberg, and it is worth zooming out to see the scale.

• Voice of America has been gutted, with Kari Lake leading the dismantling effort before being ruled to have been illegally appointed in March 2026.
• The US Press Freedom Tracker has logged around 170 reported assaults on journalists in 2026, 160 of them by law enforcement.
• An FBI search of a Washington Post reporter's home on 14 January 2026 drew widespread condemnation.
• The Varieties of Democracy Institute's 2026 report found US freedom of expression has declined to levels not seen since the Second World War.

That last point should give any UK reader pause. We tend to think of America as the country with the First Amendment tattooed on its forearm, the loudest defender of press freedom in the room. The data now puts it in territory more commonly associated with countries the State Department lectures.

At least nine lawsuits and counting

Since 2020, Trump has filed at least nine lawsuits against major media companies, according to press freedom analysts at Variety and Poynter. Most have failed. Some are pending. A few have produced settlements that look suspiciously like protection money.

The pattern is the strategy. You do not need to win every case. You just need to make every editor pause before signing off on the next critical headline. You need every general counsel to ask whether the story is really worth the legal bill. You need every broadcaster to wonder whether their licence is the next bit of paperwork to be 'reviewed.'

Why this matters for British readers

It would be tempting to file all this under 'mad American politics' and move on. That would be a mistake.

British media operate in a global ecosystem that leans heavily on US reporting. When American newsrooms self-censor, the rest of us get a thinner version of the world. Beyond that, the playbook being tested in Washington — sue, settle, regulate, repeat — is portable. It travels. Anyone who has watched the slow drumbeat of UK debates around BBC funding, Ofcom powers, and SLAPP-style lawsuits should recognise the family resemblance.

The verdict

Trump's legal scoreboard against the press is genuinely poor. Judges keep ruling against him. The constitution, occasionally, still does its job. But the courtroom is one battlefield among several, and on the others — regulatory pressure, settlement-by-attrition, executive orders, intimidation — the picture is far less reassuring.

The American press is not being silenced by a single dramatic blow. It is being worn down by a thousand small ones. Each lost lawsuit costs Trump nothing he was not happy to spend. Each settlement, each cancelled show, each early licence renewal teaches the next newsroom to think twice.

That is not a war that needs to be won in court. It only needs to be fought there.

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