'The only way to lose': Analyst explains why 'appeasement' of Trump is a doomed strategy

21 July

U.S. President Donald Trump walks before signing the "Genius Act", which will develop regulatory framework for stablecoin cryptocurrencies and expand oversight of the industry, at the White House in Washington, D.C., U.S., July 18, 2025. REUTERS/Nathan Howard

On Friday, July 18, the big media story in the United States was President Donald Trump filing a $10 billion lawsuit against the Rupert Murdoch-owned Wall Street Journal and its parent company News Corp in response to recent reporting on Trump's connection to Jeffrey Epstein. But according to MSNBC's Steve Benen, another important story on Trump and the media flew under the radar that day: the demise of Trump's almost-$50 million lawsuit against veteran reporter author Bob Woodward.

It was also on July 18 that U.S. District Judge Paul Gardephe dismissed Trump's lawsuit against Woodward, who, Trump argued, had no business publishing audio recordings of his interviews with the president for a 2020 book. Gardephe, an appointee of President George W. Bush, wrote, "There is almost no support in the case law for the notion that an interviewee has a copyright interest in his responses to interview questions, and such a conclusion would run counter to animating principles of the Copyright Act."

"In case anyone needs a fresher," Benen explains in a July 21 column, "it was in early 2023 when the Republican first filed a civil suit against Woodward and his publisher, claiming that the longtime journalist did not get his consent to release audio recordings of their interviews. Trump sought nearly $50 million in damages. He'll end up with nothing but legal bills…. The outcome was hardly unfamiliar."

The MSNBC columnist continues, "When Trump sued CNN and demanded $475 million, the case was thrown out; when he sued The Washington Post, the case was thrown out; and when he sued The New York Times, seeking $100 million, the case was thrown out. In each instance, the Republican and his legal team filed highly dubious, politically motivated cases, each of which was based on claims that can charitably be described as 'thin.' And in each instance, the journalists and their employers fought back — and won."

Woodward, now 82, became famous in the early 1970s for his historic reporting on Watergate with fellow Washington Post reporter Carl Bernstein. In 1976, Woodward and Bernstein's Watergate-related book "All the President's Men" became the basis for a Hollywood film starring Robert Redford as Woodward and Dustin Hoffman as Bernstein.

Benen notes that some major media organizations agreed to large payments to settle lawsuits from Trump — even though Trump's cases were badly flawed.

"When Trump filed a similarly weak case against ABC News," Benen observes, "the network agreed to a controversial $15 million settlement with the president. More recently, in response to a bizarre lawsuit from the president, CBS News' corporate parent agreed to an even more controversial $16 million settlement. The broader lessons should be obvious. For one thing, those wildly unnecessary out-of-court settlements only emboldened Trump, effectively encouraging him to sue other news organizations that bothered him for one reason or another."

Benen adds, "Indeed, the president explicitly referenced the ABC News and CBS News payments when outing his new civil suit against The Wall Street Journal. For another, the recent pattern suggests the only way to lose in a fight against Trump is to pursue a course rooted in appeasement. It's true when it comes to law firms; it's true when it comes to higher education; and it’s true in his court fights against news organizations."

Steve Benen's full MSNBC column is available at this link.

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