Caving to Trump: The Top Ten Worst Offenders of 2025
The newsroom leaders, tech oligarchs, law firm chairs, and university presidents who helped Trump coerce and capture large swathes of the media, the legal profession, and academia.
The defining characteristic of the Trump administration has been its radical use of state power to punish private individuals and institutions and to coerce them into bending to Trump’s ideological whims. Some targets have stood up to this harassment better than others. These are the ten most consequential capitulations to Trump in 2025.
Tim Cook, Apple CEO — Cook, like other liberal-leaning leaders of major tech companies, has worked hard to win Trump’s favor. Cook donated $1 million to Trump’s Inaugural Committee, attended the inauguration, made multiple visits to the White House to lobby Trump on tariffs, and, during one public Oval Office session, pledged an additional $100 billion in U.S. investment. Those moves may be distasteful; however, they were understandable in the face of Trump’s tariffs and other economic policies that could have been ruinous for Apple. But in September, after the assassination of Charlie Kirk, Apple made a decision to appease MAGA that was categorically different. The company pulled an 8-episode limited series, “The Savant,” about a suburban mother and a veteran who infiltrates extremist online forums and hate groups to help prevent domestic terror attacks. Unlike Cook’s earlier efforts to appease Trump, spiking “The Savant” had nothing to do with Trump’s economic threats. This was Apple tailoring its creative strategy—and selling out its actors and other artists—to appease right-wing ideological enforcers inside and outside the government who were trying to weaponize Kirk’s murder against Hollywood. Apple claimed the show would air “at a later date,” but it still hasn’t been released.
Bob Iger, Disney CEO — Quite a year for Disney. After Trump was elected, Disney, the parent company of ABC News, agreed to pay $15 million toward Trump’s presidential library (plus legal fees) and posted an editor’s note of regret to settle Trump’s meritless defamation suit over some on-air statements. In September, the company suspended “Jimmy Kimmel Live!” after a Kimmel monologue triggered a right-wing pile-on, and Trump’s FCC chair threatened the company. The show returned after a backlash to the backlash, a reminder that doing Trump’s bidding is rarely popular when the public is fully informed of the facts.
Jeff Bezos, Amazon Executive Chair — Through his meddling and gutting of the once-great Washington Post, and by leveraging Amazon’s cultural and economic power, Bezos has capitulated to Trump in many ways. In response to Trump’s obsession with DEI, Amazon ended longstanding programs to diversify its workforce, and Amazon Studios discontinued its “Inclusion Policy and Playbook,” standards intended to increase on- and off-screen representation. But the most clarifying example of how Bezos does Trump’s bidding came in April, after Trump’s initial round of tariffs. Amazon was reportedly preparing to show consumers how much the Trump-imposed import fees added to prices, a move the White House attacked as a “hostile and political act.” Trump then personally called Bezos, and the plan was scrapped.
Shari Redstone — In the most depressing merger story of the Trump era, there are few executives who came out looking good. But Redstone emerged from the long Paramount-Skydance drama as a major villain, taking a wrecking ball to CBS News's editorial independence along the way. As Paramount’s controlling shareholder, Redstone ran the parent company of CBS when it made one of the most shameful decisions of any media conglomerate in recent history: paying Trump $16 million to settle an absurdly frivolous lawsuit against “60 Minutes,” a payment that was credibly described by several Democratic senators as a potential illegal bribe. Redstone’s caving to Trump via the settlement and her subsequent attempts to monitor the show’s coverage of Trump to win FCC approval for the Skydance deal led the head of CBS News and the executive producer of “60 Minutes” to resign, and paved the way for the new pro-MAGA editorial climate at the once-celebrated news show. Redstone, who reportedly earned over $500 million from the deal, later said the settlement with Trump was the “right decision.”
David Ellison, Paramount Skydance CEO — Redstone’s partner in turning CBS News into a safe space for the president and his allies, Ellison readily caved to unusual FCC mandates in order to win the commission’s blessing for Skydance to take over CBS’s broadcast licenses. At the government’s direction, Ellison also agreed to hire an ombudsman to review complaints, ensure that CBS News programming is “free of bias,” and end any DEI programs. It amounted to full-on government meddling in the editorial independence of a major news entity, setting a precedent that future administrations—on the right or left—will surely remember.
Mark Zuckerberg, Meta CEO — After the January 6 insurrection at the Capitol, Facebook suspended Donald Trump’s account “indefinitely” because “the risks of allowing President Trump to continue to use our service during this period are simply too great.” Trump sued Facebook over the suspension a year later—a lawsuit that Facebook told a court was without merit, used legal theories that have been “rejected repeatedly,” and “should be dismissed with prejudice.” Then Trump was re-elected, and Zuckerberg’s new era of capitulation began. Zuck’s first move was to pay a $25 million settlement to Trump, with most of the money earmarked for Trump’s presidential library.
Brad Karp, chairman of Paul, Weiss, Rifkind, Wharton & Garrison — When Trump began targeting law firms with spurious executive orders, Karp was the first head of a firm to cut a deal with the White House rather than fight. Karp’s early capitulation to Trump signaled to the rest of the legal industry that caving was an acceptable response. The embarrassing deal, which required Paul Weiss to do $40 million worth of Trump-friendly pro bono work, triggered a stampede of big law firms racing to the White House to seek similar agreements, whether or not they were mentioned in Trump’s original executive orders. Karp’s decision looked even worse when other large firms targeted by Trump—Perkins Coie, WilmerHale, Jenner & Block, Susman Godfrey—challenged Trump in court and won decisive victories. One federal judge called the Trump orders “a shocking abuse of power,” and another judge said the orders were “an unprecedented attack on” America’s “foundational principles.”
Claire Shipman, Columbia University acting president — In July, after months of attacks and investigations by the Trump administration, Columbia agreed to pay $221 million in fines and made a series of unprecedented concessions that ceded control over aspects of the school’s policies on admissions, hiring, promotions, and curriculum to the federal government. Like Karp and the law firms, Shipman’s capitulation made it safer for schools across America to buckle, an outcome that Trump officials celebrated. “It is our hope this is going to be a template for other universities around the country,” Education Secretary Linda McMahon said after the deal was announced. “We’re already seeing other universities taking these measures before investigation.” Critics called Columbia’s decision caving to “exhortation” and warned that it was “likely to provide cover for the Trump administration’s ongoing, lawless assault on higher education.” Brown, UVA, Cornell, Northwestern, and others have all fallen in line since then.
Sundar Pichai, Alphabet (Google) CEO — Like every other tech oligarch, Google has accommodated itself to Trump in numerous ways this year—paying $24.5 million to settle a frivolous Trump lawsuit over his YouTube suspension, rolling back its diversity goals, backing away from EU disinformation “fact-check” commitments, removing Google calendar observances for Pride Month and Black History Month—but there was one Trumpian change this year made to Google’s omnipresent products that stands out above the rest. In February, Google Maps, used by 1 in 4 people on Earth, began displaying the Gulf of Mexico as the Gulf of America.
Bari Weiss, CBS News editor-in-chief — One of the most consequential stories of 2025 was how corporate media became captured by the Trump administration, and nothing exemplifies this trend more than the depressing drama of how David Ellison came to control CBS News and install Weiss to refashion it as a MAGA-friendly outlet. I like Weiss and had hoped, against the available evidence, that she would prove her critics wrong and not end up as a tool for the ideological and corporate pursuits of her boss. But so far, the critics are looking prescient. Whatever one thinks of the alleged left-leaning slant at CBS, what’s needed now more than ever is a news media that is unapologetically oppositional to those in power, not an editor-in-chief who thinks obsequiousness is a corrective to perceived bias. This was all predictable. In the Biden years, The Free Press under Weiss was an exciting contrarian publication, but now it too often reads like long apologias for Trumpism. At CBS, Weiss is making the same mistake she made running her niche Substack publication: believing that in the age of Trump, the most serious illiberal threats come from the left. That mistake is far more consequential now that she’s applying her misdiagnosis of American politics to the enormous global platform of CBS News. Here’s hoping she reverses course in 2026.
Anyone else find it funny that Bari Weiss is basically an IRL version of Olivia Nuzzi's TV show pitch main character? Gay former liberal journalist who becomes a de facto regime media censor out of a pure fascination and obsession with power... It's too perfect.
You know, Ryan, I really enjoy your writing and even pay for it (although I wish you'd get back to the Olivia chronicles) and I'm … gasp … totally MAGA. All it takes to cave in to Trump is to live in my small coastal California City amid houses with “in this house” lawn signs and out in our channel Katy Perry cavorting with Justin Trudeau on her Caravelle yacht and you look at Bari Weiss and think “she never looked this happy working at NYT and hey, she's even showing her rack now.” Happy New Year, Ryan. I hope you sell the Olivia story as a series. It's too good a guilty pleasure for it to stop.