Greetings and a warm welcome to *Regulator*. Not long ago, I found myself gliding through downtown Washington, D.C., on a bright green Lime scooter — yes, I admit it without shame — darting through traffic at the bustling intersection of 16th Street and I Street NW. As I zipped by, a familiar building caught my eye: the office of the Motion Picture Association. But something had changed. Its recognizable emblem had been replaced by the insignia of *America 250*, gleaming above the doorway like a new badge of purpose. The last time I had encountered this particular nonprofit, it was not in a quiet city moment but amid the brash spectacle of the 2025 Bitcoin Conference, where America250 was busily pressuring the cryptocurrency sector to fund one of President Donald Trump’s most divisive passions — his much-debated military parade.
In the months that followed that encounter, it seems America250 — officially a nonprofit organization established by Congress to orchestrate the nationwide celebrations honoring the 250th anniversary of the Declaration of Independence — had expanded its funding operations with renewed vigor. The building’s entryway now displayed a constellation of corporate logos: Netflix, Amazon MGM Studios, Disney, Paramount, Sony, and Universal Studios. Each of these entertainment giants appeared to be lending its name and likely its money to the America250 initiative. The coincidence was striking: at least three of these firms were simultaneously engaged in corporate mergers undergoing scrutiny that required signoff from none other than the Trump administration.
This scene dovetailed unexpectedly with the reporting project occupying my attention that week — a deep investigation into the chain of events behind *YouTube’s astonishing $24.5 million settlement* in a lawsuit initiated back in mid-2021 by Trump and several of his close MAGA allies. In an alternate political universe, the plaintiffs might have prevailed in court, arguing that YouTube had infringed on their First Amendment rights when it suspended their channels. However, under American law, YouTube, as a private company, is not beholden to such constitutional constraints; it retains the freedom to determine who may or may not use its platform to publish content.
Yet the reality we inhabit is far different. In this version of history, Trump secured reelection and now directly presides over a regulatory apparatus that exercises an extraordinary degree of influence over Google and its many subsidiaries. Upon returning to power, Trump inherited two Department of Justice antitrust suits filed against Google, each having already yielded findings that the tech titan had maintained unlawful monopolies in distinct spheres — online search and advertising technology. Although Google has, so far, avoided a forced divestiture of its indispensable web browser, Chrome, it currently faces a high-stakes remedies trial that could determine whether it will be compelled to relinquish control of its ad tech exchange.
What technology executives are beginning to grasp — a lesson well known to the cutthroat veterans of Trump’s inner circle — is brutally simple: survival in Trump’s America depends less on compliance and more on affection. To avoid falling from favor, one must endear oneself to the president on a personal and transactional level, ensuring he prefers you more than the adversaries he delights in punishing.
Trump’s fondness extends most easily to those he has entrusted with carrying out his vendettas against perceived enemies — in media, technology, and politics — and who can deliver tangible victories. There are numerous examples: FCC Commissioner Brendan Carr momentarily succeeded in nudging Jimmy Kimmel off the airwaves; Attorney General Pam Bondi famously orchestrated the arrests of Trump’s rivals after he publicly clamored for retribution on Truth Social; and even Elon Musk enjoyed a brief stint within Trump’s good graces when his ventures coincidentally aligned with the administration’s goal of dismantling large swaths of the federal bureaucracy. A Republican lobbyist specializing in technology policy confided to me that the administration is now saturated with fervent anti–Big Tech loyalists bent on dismembering Google, even if the company survives its current legal tests. “The threat is always there,” he told me curtly. “It’s like a gun left permanently on the table.”
Yet, the enduring enigma within Trump’s governance is his internal calculus: does he ultimately value the allegiance of impoverished loyalists or the deep pockets of corporations capable of writing enormous checks — particularly when he can redirect those funds toward the self-aggrandizing projects he favors? Earlier this year, for instance, Trump decreed that the settlement proceeds from his lawsuits against Twitter and Meta — totaling $10 million and $25 million respectively — should be allocated toward constructing his presidential library. According to attorney John P. Coale, who represented Trump in those same cases as well as the one against YouTube, the president specifically wanted his portion of the YouTube settlement redirected to building a new, 900-seat ballroom within the White House. “Everybody’s happy,” Coale observed matter-of-factly. “Trump’s happy, the plaintiffs are happy.”
If preliminary reporting holds true, this so-called ‘White House ballroom fund’ may soon become another America250 in spirit: a quasi-charitable conduit through which technology firms can funnel millions under the guise of civic philanthropy while effectively underwriting Trump’s vanity infrastructure. In August, the White House publicly stated its intent to raise $200 million from private donors for the ballroom’s construction; astonishingly, within only two months, it was reportedly nearing that goal. Simple arithmetic makes one detail stand out — YouTube alone financed nearly 11 percent of what Trump has proudly dubbed the “Big, Beautiful Ballroom,” a design he claims was inspired by his own Scottish golf resort’s grand hall.
While I was taking note of these developments in Washington, journalist Lauren Feiner was stationed in a Virginia courthouse, covering the ongoing Google ad tech remedies trial. After the final gavel of that session fell, we spoke about her observations. She explained the existential stakes now confronting Google and why, from the company’s pragmatic perspective, a $22 million financial concession might seem a small price to pay compared with the potential devastation that could arise from an unfavorable judgment. Even if such payments cannot ultimately safeguard Google from the unrelenting scrutiny of MAGA-aligned antitrust crusaders, for the moment, everyone wins: Trump gains his opulent ballroom and YouTube secures a sizable tax deduction.
Feiner noted that the case against Google remains rooted in longstanding legal traditions that predate the Trump era, despite the radical tone of current politics. Much of the litigation originated under Biden’s administration, prosecuted by his appointees. Though Trump’s Department of Justice has steered policy in more constitutionally questionable directions, the core arguments in both of Google’s antitrust trials have, to her surprise, remained consistent. The ad tech trial itself concluded this Monday, with closing arguments scheduled for November. If procedural continuity persists, Google may soon face serious structural repercussions.
Feiner went on to describe how each case represents a different piece of Google’s economic foundation. The search lawsuit strikes at the very heart of the company’s business model — the element most people instinctively associate with Google — while the ad tech trial involves the complex, often-overlooked infrastructure that underpins much of online advertising. These proceedings collectively illuminate how Google allegedly leveraged its dominance across multiple market segments to perpetuate unfair advantages. The outcome could reshape not only one company’s operations but also the broader financial ecosystem sustaining digital publishing.
Indeed, revenue derived from open web displays — the advertisements users encounter flanking news stories or adorning independent blogs — sustains countless publishers from small startups to legacy institutions like *The New York Times* and *The Wall Street Journal*. As AI-driven interfaces begin to disrupt traditional online engagement, this revenue stream is shrinking, though still vital. Thus, the court’s eventual decision holds significance well beyond Google’s corporate boundaries; it speaks to the future economics of journalism itself.
The intriguing continuity across administrations cannot go unnoticed. Even after personnel upheavals within Trump’s Department of Justice — including the headline-making dismissal of two senior antitrust officials following a disputed merger approval — the government’s stance in both Google cases has remained consistent, suggesting institutional inertia deeper than partisan politics. Yet observers throughout Washington wonder whether this delicate balance can withstand Trump’s mercurial impulses.
Feiner acknowledged that both the DOJ and the FTC are juggling numerous high-profile cases against Big Tech firms simultaneously — effectively squaring off against all four industry titans at once. Settlements, such as the recent resolution of the Amazon Prime case, which falls under consumer protection law rather than antitrust statutes, offer glimpses into possible compromises. However, the sheer magnitude and political profile of the Google proceedings make it unlikely that these matters will quietly fade.
Speculation continues regarding Trump’s personal involvement. Although he has refrained from commenting directly on Google’s lawsuits, his prior interactions with CEOs reveal his transactional approach. Recently, he even mused publicly about breaking up Nvidia before abruptly changing tone after a conversation with the company’s leadership. The pattern is familiar: Trump’s opinion often shifts in direct proportion to the flattery he receives or the perceived loyalty of business interlocutors. Many recall how his meeting with Mark Zuckerberg prior to the Meta trial triggered fears among antitrust advocates that a settlement might emerge through personal persuasion rather than policy. To date, however, no such preferential interference has materialized.
Feiner also observed an underappreciated truth in public coverage: amid all the legal maneuvering, Google has already been found liable for maintaining monopolistic practices. The current phase is less about guilt or innocence and more about the scale of remedial action — what, specifically, the company might lose. As Google executives defend their creations as beneficial to both users and publishers, they face a judiciary that has already determined those same tools inflicted measurable harm on competitors and the open web.
In court, a parade of CEOs from rival firms testified about how Google’s practices stifled their businesses, while others, including figures from OpenAI, speculated enthusiastically about acquiring parts of Google’s empire — notably Chrome — should regulators force divestitures. Even when enthusiasm appeared muted, the underlying motive was unmistakable: the opportunity to claim a fragment of one of the world’s most profitable data ecosystems is irresistibly appealing.
In the end, whether through settlements, lawsuits, or so-called charitable contributions, the line between public governance and private interest continues to blur. Trump’s America thrives on this ambiguity, transforming every legal challenge and every donation into a potential transaction of loyalty. For now, the grand ballroom rises in marble and gold, YouTube’s check clears the account, and the machinery of politics and technology spins inexorably onward — its participants smiling, its stakes immeasurable.
Sourse: https://www.theverge.com/column/794975/big-tech-trump-nonprofits-donations-regulator
