Lawlywoodland: Truth, Justice & the American Way

You must catch the deer before you can skin it.

—A legal writer in medieval England

Greetings from an increasingly chaotic and disorienting United States, where we now appear to be hydroplaning through The Widening Turn. In 2025, the pursuit of innovation as a means to achieve a new kind of AI-enabled power in an increasingly multi-nodal (ie, multi-polar) world is a fraught process.

One of the wildest aspects of our current situation? All the ongoing legal maneuverings sparked by the clash between a particularly aggressive White House and an increasingly outraged ancien régime. America’s legal dramas—featuring layers of intrigue, power struggles, and not a few threats—are making the country look more and more like the set of a classic Hollywood noir thriller.

Welcome to Lawlywoodland.

The Innovator's Dilemma for Government

Why does this all matter? Because technological disruption is afoot, and the economy is in the uneven process of shifting to a generalized AI platform. And in the "Age of AI," the regulatory system in which technology operates is as important as the technology itself. It’s therefore worth wondering how the current disruption might affect how business gets done in the United States. How might business models for enterprises, the telecom sector, and the BPO space be impacted?

To make matters even more confounding, the U.S. legal system features often conflicting federal, state, and local laws. When it comes to the realm of AI governance in particular, there’s an extended tangle of sectoral regulations, executive orders, and tentative legislative efforts. We also happen to be witnessing a series of federal trials that are weighing antitrust break-ups of Big Tech firms like Meta Platforms and Google.

And so one might also wonder—what strange new technology-focused rules will emerge from our regulatory thicket? Will the regulatory environment impede AI’s economic impact or feed its full potential?

When it comes to President Trump’s mercurial tariff policies, it's also worth wondering how investors are supposed to effectively evaluate companies that import goods or engage in international commerce. What kind of future does a coherent set of AI policies have amidst all this chaos?

After all, we’re living at a time when laws that are passed could be outdated within minutes. What happens when new regulations quickly become obsolete in an environment of rapidly advancing technology?

It's nothing less than “The Innovator’s Dilemma” for the American government.

Judicial Questions: Rewriting the Rules

While Alexis de Tocqueville was right two centuries ago when he observed that, “There is almost no political question in the United States that is not resolved sooner or later into a judicial question,” Donald J. Trump is breaking the mold. The most urgent question right now is whether Trump, as president of the United States, has the legal authority under the International Emergency Economic Powers Act (IEEPA) of 1977 to impose sweeping tariffs that are rocking the global trading system.

According to Professor of International Relations Paul Sracic, “The law’s purpose was to address genuine crises—like foreign aggression or economic sabotage—not to serve as a catch-all to implement domestic policy preferences. Mr. Trump’s reciprocal tariffs stretch IEEPA beyond its intended scope, sidestepping Congress’s constitutional authority over trade and taxation.” In this view, Trump’s moves are a case of executive overreach, with the president claiming unilateral power to tax and regulate commerce, powers vested in Congress under Article I, Section 8 of the U.S. Constitution—

President Trump relied on the International Emergency Economic Powers Act to impose last week’s reciprocal tariffs.... This expansion of executive authority clearly oversteps the boundaries set by the Supreme Court’s major questions doctrine. Prominent in recent judicial rulings, the doctrine holds that federal agencies—and the executive branch—can’t make decisions of vast economic and political significance without clear congressional authorization.

For his part, the president argues that the fentanyl epidemic, not to mention the decades-long hollowing-out of the American working-class, combined with the continuing tsunami of China's global exports, is indeed a national emergency.

And so it seems inevitable that the United States Supreme Court, “the most powerful court in the world,” will eventually decide the matter. “That may be the only way to restore the delicate balance of power that defines American governance,” says Sracic.

But in the meantime, a host of other vexing policy questions abound. For example, was it legal for the Trump administration to send migrants to a prison in El Salvador without first holding a hearing? Are the Trump administration’s myriad demands on colleges and universities constitutional, including the deportation of student protestors? What about the legality of mass layoffs across the federal government spearheaded by DOGE?

“In carrying out his campaign,” observes one reporter, “Mr. Trump’s actions often combine political clout, command of public attention and control of some federal spending, sometimes wrapped in language that is a cross between social media post and a legal brief.”

According to the editorial board of The New York Times, “(Trump) is straining the American system of checks and balances in ways it has not been tested in many decades.” For the editorial board of The Wall Street Journal, “President Trump is exercising executive power in aggressive and often novel ways.”

Lower Court Judges Rise Up

In response, a fusillade of nationwide injunctions against Trump’s executive orders are being issued by a number of federal district court judges. But does the issuing of such injunctions outside the confines of a certified nationwide class action translate to judicial overreach? Are unelected lower court judges able to overrule the executive branch?

Based on The Federalist Papers, Alexander Hamilton would point to the judiciary as the weakest of the three branches of government. And one suspects Thomas Jefferson—always wary of giving the lawyer class unbridled power in society—would point to the Declaration of Independence itself, which warned against dictatorial judges.

For now, as the Supreme Court begins to weigh in on all the litigation and injunctions confronting the administration, the justices appear intent on imposing some order. “Technical details of the rulings aside, the justices are reminding Trump-hostile lawyers and lower court judges that they have a duty to follow the rules on venues, cause of action, jurisdiction, and standing—and to exercise a little judicial modesty.”

In one court case that has many worrying about the independence of the Federal Reserve and its ability to conduct monetary policy free of interference, Supreme Court Chief Justice John Roberts just reversed a lower court ruling and allowed President Trump to proceed with the firing of two officials who lead independent agencies. As David Wilcox of Bloomberg puts it, "Their legal situation is the same as that of Federal Reserve governors, making the outcome of their cases pivotal to the Fed's own independence.... It's increasingly clear the issue eventually will be argued before the Supreme Court."

And this week the Supreme Court endorsed part of a trial judge’s order requiring the government to “facilitate and effectuate the return” of a Salvadoran migrant who was wrongly deported to a prison in El Salvador. But the court also "stopped short of ordering the return of the migrant, Kilmar Armando Abrego Garcia, indicating that courts may not have the power to require the executive branch to do so.... The case will now return to the trial court, and it is not clear whether and when Mr. Abrego Garcia will be returned to the United States."

But that's just for starters. Trump-adjacent legal questions are spreading like wildfire all across Lawlywoodland. And the wide-ranging and unrelenting aggressiveness of Mr. Trump's policy actions suggest a struggle with elements of the American Establishment that will have wide-ranging consequences.

AI Accelerationism & Rules Governing the Tech Industry

In September, 2023, top tech leaders made their way to Capitol Hill for a summit endorsing strict AI regulation in the United States. It was a moment of high drama that reached its crescendo with Elon Musk warning of “civilizational risks” posed by AI’s relentless march.

That was a lifetime ago. At warp-speed, we’ve skidded into the spring of 2025. American tech accelerationism is all abloom. Tech leaders now seek to vanquish excessive regulation and press ahead with pro-growth AI policies. OpenAI is raising the specter of DeepSeek, insisting that if Chinese developers “have unfettered access to data and American companies are left without fair use access, the race for AI is effectively over.” And so OpenAI urges the U.S. government to turn over as much data as possible to feed into its systems.

The King of Lawlywoodland, Donald J. Trump, says he agrees. He now declares that advancing AI is key to outpacing China in the race to innovate. On his first day in office, the president signed an executive order rolling back safety testing rules for AI used by the government. Two days later he signed another order asking industry to make suggestions on how best to, “sustain and enhance America’s global AI dominance.” That second AI executive order, “Removing Barriers to American Leadership in Artificial Intelligence,” mandates the development of a pro-growth AI policy within 180 days.

On March 25, 2025, Michael Kratsios, a Peter Thiel protégé who also worked in the first Trump administration, was confirmed by the U.S. Senate to lead the Office of Science and Technology Policy (OSTP). He's now sifting through thousands of suggestions companies have submitted for the administration's AI plan. His experience as a visiting scholar and instructor at China’s Tsinghua University, which is known for producing top engineering talent, will help him think deeply about how AI and national security collide in the race for technological supremacy with the Middle Kingdom. “The stakes," he said, "are a lot higher this time around."

As night follows day, lobbying firms are looking to capitalize on Trump’s deregulatory agenda and the fast pace of change; this year’s mantra at one D.C. firm (Invariant) is “chaos creates opportunity.” And the opportunity is huge—

Federal lobbying spending hit a record high in 2024, with companies, nonprofits and other interest groups shelling out $4.4 billion to influence policymakers. Meta Platforms was the largest big tech spender, dropping more than $24 million last year as policy debates roiled over privacy, free speech and child safety issues. In the fluid political landscape of 2025, these spending trends are likely to continue as the rules governing the tech industry get rewritten.

A giddy tech community crackles with ideas. “Meta, Google, OpenAI and others have asked the Trump administration to block state AI laws and to declare that it is legal for them to use copyrighted material to train their AI models. They are also lobbying to use federal data to develop the technology, as well as for easier access to energy sources for their computing demands. And they have asked for tax breaks, grants and other incentives.”

Meta has been particularly aggressive in prowling through Lawlywoodland hunting for legal access to more copyrighted works, pushing “the White House to issue an executive order or other action to ‘clarify that the use of publicly available data to train models is unequivocally fair use.’”

However, other forces are attempting to push back against Big Tech. Recently, federal Judge Sidney Stein rejected OpenAI's request to toss out a copyright lawsuit from The New York Times claiming the tech company exploited the newspaper's content without permission or payment. Attorney Steven Lieberman celebrated the judge's ruling by saying, "We appreciate the opportunity to present a jury with the facts about how OpenAI and Microsoft are profiting wildly from stealing the original content of newspapers across the country.”

Finally, while Meta and other tech firms lobby the White House to endorse open-source AI, the Center for AI Policy, a think tank and lobbying group, shouts HOLD ON!... we need third-party audits of systems for national security vulnerabilities!

Trump vs. Big Law

Meantime, if and when the Trump administration's vision for the future role of technology in American society starts to coalesce, and its plans for AI approach some kind of coherence, Lawlywoodland’s vast armies of lawyers will be in the thick of the scramble, many of them working on behalf of lucrative corporate clients.

In which case, what will it look like for Big Law, counsel to the world’s most powerful corporations, to thrive in the new world emerging? Alas, Big Law, which is “engaged in every sector of the marketplace and central to ensuring that the United States and global economy continue to spin,” is currently under attack.

Because the King of Lawlywoodland has declared all-out war on the kingdom’s legal institutions—

He has moved to purge the Department of Justice of all but those he perceives as loyal to him personally, demanded changes to law school curriculums, called with increasing furor for the impeachment of judges with whom he disagrees, attacked by name public-interest attorneys and bar associations that oppose his policies, and inched perilously close to defying court orders outright. In recent weeks Mr. Trump has also gone after the nation’s leading law firms—Covington & Burling; Perkins Coie; Paul, Weiss; and many more—with measures meant to hobble their ability to do business.

As The New York Times tells it, “President Trump’s campaign to get business leaders to play by his rules has sowed confusion and outright concern in C-suites amid escalating attacks on corporate America. The case of Paul, Weiss could stand as Exhibit A.” In brief, President Trump targeted that particular firm with an executive order that could have crippled its business.

Responding like a startled deer, Brad Karp, chairman at the firm, and a group of partners decided that it made more sense to broker a deal with the president instead of engaging in a drawn-out legal battle. And so “Karp and Trump met in the Oval Office, reaching an agreement on a number of concessions, including a pledge to provide $40 million in pro bono legal services on issues the president has championed.”

“In deciding to bend to Mr. Trump,” noted another piece in the Times, “Mr. Karp likely saved his law firm, which had $2.63 billion in revenue last year and represents corporate clients like Exxon Mobil and Apollo Global Management, from hemorrhaging clients and lawyers.” Karp argued he had no choice. After all, rivals to Paul, Weiss were lurking throughout Lawlywoodland, looking to poach top lawyers from the wounded firm. As Princeton Professor Deborah Pearlstein puts it, “If the firm can just avoid open antagonism of the governing regime, the thinking may go, then it will survive until the turbulence subsides.”

But soon enough, law firm Jenner & Block also received its own executive order that accused it of engaging in “lawfare” and engaging in activities “that undermine justice and the interests of the United States.” Andrew Weissmann, a former partner at the firm, had once investigated alleged ties between Donald J. Trump’s campaign and Russia during his first term.

As for the foxes at elite law firm Skadden, Arps, Slate, Meagher & Flom, it too decided to seek out a preemptive deal with Trump’s advisors in order to save itself from the Lawlywoodland regime’s fury. “The talks represent an extraordinary turn in Mr. Trump’s campaign against law firms and the legal system more broadly, marking what appears to be the first time that a major firm has tried to cut a deal with the president before he could issue an executive order.” It wasn’t long before Skadden, Arps agreed to provide $100 million in pro bono work on issues President Trump supports and, according to the president, declared a “strong commitment to ending the weaponization of the justice system and the legal profession.”

But there was also internal pushback when “a group of alumni—all part of the law firm’s prestigious public interest fellowship program—began to circulate a letter. It urged the firm's leadership to ‘take every measure to resist unlawful interference with the rule of law, to fight any unjust actions’ and ‘to speak publicly about the critical, nonpartisan role of lawyers in defending democracy.’”

As the internal dissent gained momentum, Skadden leadership moved to squelch its spread. Some associates were blocked from announcing their resignations widely on Skadden’s email channels. “Two other associates said Skadden’s email system had not allowed them to send messages about their concerns about the deal to broad groups of lawyers. Those associates spoke on the condition of anonymity because they still work at Skadden.”

Days later, Trump was back on the hunt, like Henry VIII pursuing his prey on horseback through an English forest, issuing an executive order suspending the security clearance for WilmerHale, once home to former FBI director Robert Mueller III, one-time special counsel on the investigation into alleged Russian interference in the 2016 presidential election. The executive order accuses the firm of hiring lawyers who “weaponize” the legal system and engage in “partisan representations,” among other things.

“We look forward,” responded WilmerHale, “to pursuing all appropriate remedies to this unlawful order.” Perhaps they’re channeling the fighting spirit of Perkins Coie, another law firm willing to go to court to fight Lawlywoodland’s leader. Perkins Coie scored a small win when Beryl A. Howell of the Federal District Court for the District of Columbia issued an order temporarily barring a major portion of Trump’s order from taking effect, suggesting it reflects “retaliatory animus” and is unconstitutional. “I am sure that many in the profession are watching in horror at what Perkins Coie is going through,” the judge said. “It sends little chills down my spine.”

A day later, Judge John Bates and Judge Richard Leon of Federal District Court in the District of Columbia both issued temporary restraining orders blocking much of Trump’s executive orders targeting Jenner & Block and WilmerHale. But while the rulings barred punishments described in the executive orders like banning their lawyers from government buildings, meetings, or jobs, the judges let stand the parts of the president’s orders stripping security clearances from lawyers at the firms.

Jenner & Block and WilmerHale seem determined to build on that momentum, filing court papers seeking to permanently block executive orders that threaten their businesses and ability to represent clients in matters involving the federal government. “In its filing, Jenner & Block said that the executive order was ‘a plain violation of the First Amendment’ and that it punished the firm for representing clients President Trump did not like.” In its filing, WilmerHale said that “retaliatory animus and viewpoint discrimination infect every aspect” of the president’s order.

As for President Trump, the king of Lawlywoodland remained blithely confident in his hunting skills, like Henry VIII on his throne. “They’re all bending and saying, ‘Sir, thank you very much,’” he said, adding that law firms are saying, “‘Where do I sign? Where do I sign?’”

At the same time, a mercurial Mr. Trump has also suggested that some law firms that settle with the administration might help negotiate trade deals with countries he’s hitting with tariffs. “We’re going to have to use those, those great law firms, I think, to help us with that,” he pronounced.

For William McGurn of The Wall Street Journal, “In the end, almost all the litigation against President Trump comes down to this question: Does the law give him the authority to do what he is doing? Whether it is the right thing to do is a separate, political question that is not for the courts to decide.” Ultimately, the United States Supreme Court will need to decide the issue of a president’s executive authority and whether Trump has the constitutional power to continue with his hunting habit.

Enter D. John Sauer, just confirmed by the Senate, 52 to 45, to be the U.S. solicitor general—the top Justice Department official representing the federal government in arguments before the Supreme Court. Mr. Sauer will be, “in charge of Mr. Trump’s aggressive attempt to get the Supreme Court to intervene in a series of cases in which lower court judges have temporarily blocked wide pieces of the administration’s agenda.”

It's useful to recall that it was Sauer who represented Mr. Trump in his presidential immunity case last year by arguing that, “A former president could be immune from prosecution even if he ordered SEAL Team 6 to assassinate a political rival.” No wonder Big Law is running scared through Lawlywoodland.

However, there’s still work to be done for the foxes that remain on the prowl. Akin, Gump, Strauss, Hauer & Feld, which employs over 50 lobbyists, is staying focused on “helping clients navigate rapidly changing trade policy and coming AI regulation.” One of their specialties is defense tech. And a lot of their work “boils down to promoting national security and strategic competition with China.”

Indeed, well before President Trump unleashed a swarm of executive arrows at the forces of Democratic-leaning law firms as if he were Henry V at the Battle of Agincourt, Paul Weiss was one firm that was already repositioning on the chessboard. It seems that the firm “had begun to take down some references to its public interest work that conflicted with the administration.” It also appears Paul Weiss’s fox-like Mr. Karp “was prepared to offer pro bono work on causes supported by Mr. Trump, including helping the administration launch a sovereign wealth fund.”

As one outraged former federal prosecutor put it, “We’re in a unique moment where the rule of law is being threatened and part of lawyers’ duty as professionals is to uphold the rule of law and fight back…. And law firms are uniquely positioned to wage these battles but were more worried about their bottom lines.”

And after Willkie Farr & Gallagher joined the list of law firms striking a deal with the White House, pledging $100 million in legal services to causes that the Trump administration supports, its longest-serving lawyer, Joseph T. Baio, resigned. In an email to the firm’s executive committee, Baio explained that he had left so he could “join the fight against governmental tyranny, unconstitutional decrees and social injustice, particularly at this critical time.”

Plot Twist: The Smith-Mundt Act

If, dear reader, you’re wondering why the president of Lawlywoodland seems to have morphed into a Mad King on the warpath against Big Law, it’s important to understand it’s because he believes he’s been the victim of unremitting lawfare and information warfare that some of Big Law's cagiest Democrat-leaning attorneys (in hushed whispers behind the hand) helped support.

And to understand the logic behind such thinking, we need to go back to the year 2012.

You’ll recall that in 2012, Lawlywoodland was being buffeted by the churning after-effects of the Great Financial Crisis of 2008-2009, and lots of Americans were agitated and angry as they crawled out of the Great Recession. It was also a time when social media platforms were rapidly gaining scale and impact. Millions were online charging the U.S. government with breaking the social contract by leaving them high-and-dry while bailing out the Big Banks. It was a volatile situation that spawned protest movements such as Occupy Wall Street.

Meantime, something else was happening too—the competition between the United States and China was heating up, and both empires seemed to understand that the economic climate had the potential to destabilize their respective social orders in all sorts of insidious ways, which could in turn potentially impede their respective preparations for the next stage of the great tech war both knew was imminent. As a result, the governments of both great powers proceeded to make decisive moves to gain more influence, even control, over their domestic populations.

In the United States, that meant plans to “modernize” a piece of legislation passed by the 80th U.S. Congress and signed into law by President Harry S. Truman back in 1948 known as the Smith-Mundt Act. The Act was meant to regulate the broadcasting of programs for foreign audiences produced under the guidance of the U.S. State Department. But one of its provisions also strictly prohibited domestic dissemination of materials produced by such programs. In other words, the American people would be protected from being propagandized by their own government even as American influence campaigns took off overseas.

By 2012, thinking had changed due to fast-moving circumstances (ie, a traumatized financial system and the expanding reach of online platforms). And so the Smith-Mundt Modernization Act of 2012 (HR 5736) amended the restrictions of the original act. As of 2013, materials produced by the U.S. State Department and the Broadcasting Board of Governors (BBG) could be spread within the United States to shape domestic narratives and influence public opinion (“To amend the United States Information and Educational Exchange Act of 1948 to authorize the domestic dissemination of information and material about the United States intended primarily for foreign audiences, and for other purposes”).

To make things even more interesting, changes to Smith-Mundt were made the very same year that President Xi Jinping came to power in China pushing through similar methods of influence and control over his population. Alas, “Since rising to power in 2012, Mr. Xi has transformed China’s media landscape, restoring the primacy of party-controlled news outlets while silencing independent voices.” As in the United States, China’s new approach to media and internet governance was gathering steam.

A revision to China’s National Security Law made internet security a key component of national security, including the concept of “cyber-sovereignty.” The revised law included special legal controls, including provisions for the administration of internet news. In effect, a battle of narratives between two great empires on opposite sides of the globe was being ratcheted up even as threats to free speech intensified within both realms.

Such was the information ecosystem into which Donald J. Trump rode his escalator when he announced his run for the U.S. presidency in 2015. Concerned critics of changes to Smith-Mundt had argued that it would enable the dissemination of disinformation across the media landscape. And sure enough, it wasn’t long before we Americans were inundated with far-fetched claims that Mr. Trump was a Russian spy.

Was there a connection to the Smith-Mundt Modernization Act? Although Smith-Mundt hadn’t been updated with Trump in mind, it may have offered a convenient and tempting set of tools for those in power once Trump's insurgency shook American politics and threatened dramatic changes to the global trading and security systems long embraced by the American Establishment.

The unproven yet unrelenting accusations against Trump dominated America’s news ecosystem for years. Americans were being bombarded with a tale that read like a spy thriller or classic film noir detective saga. It was impossible to look away.

Unsurprisingly, according to a PBS News Hour/NPR/Marist College poll in July, 2017, 54% of Americans believed Trump’s dealings with Russia were unethical or illegal. According to a July, 2018 Quinnipiac University National Poll, fully half of American voters believed, "that the Russian government has compromising information about President Trump.”

Whatever the possible connections between the modernization of Smith-Mundt that took effect in 2013 and the information offensive against Donald J. Trump that commenced in 2015, one person now looking to restore the original Smith Mundt Act is none other than Elon Musk.

You see, Musk and others now note that, in just one example, the United States Agency for International Development (USAID) "sponsored Kiev-based outfits like Molfar, CCD and VoxUkraine as they sought to destroy the reputations of US politicians.” Trump and his team were determined to shut-down an information warfare apparatus that funneled money overseas which ended up funding stories that defamed critics of the Ukraine war like J.D. Vance and Tulsi Gabbard, portraying them as foreign agents.

This was doubtless part of the logic behind Trump going after not only USAID, but the U.S. Agency for Global Media as well, whose mission was supposed to be “to broadcast accurate news and advocate for American ideals around the world.” So much for that. In a March 14, 2025, executive order President Trump, ”called for the elimination of the U.S. Agency for Global Media to the extent possible by law. The agency oversees five international broadcasters, including Voice of America.”

Truly, in the early 21st century, Lawlywoodland has morphed into a shadowy bog where truth and fiction are engaged in a constant struggle for control. A confluence of Big Law, Big Tech, Wall Street, and Capitol Hill has morphed into a giant scrum scrambling to define the future development of American society. And at the center of it all is Donald J. Trump, a ruler widely feared across the kingdom. As William A. Galston of The Wall Street Journal notes, “Creating fear is his go-to strategy for inducing people to comply with his wishes. If threats don’t suffice, he moves against vulnerable individuals and institutions, making examples of them to terrify others into obedience.”

The viciousness of the struggle between a president with a maximalist view of his powers and an outraged ancien régime seems almost medieval. And the fact that American law is based on English Common Law brings to mind something Peter Ackroyd pointed out in his book, Foundation: The History of England from its Earliest Beginnings to the Tudors—

One of the paradoxes of medieval society lies in the presence of extreme violence and disorder alongside an appetite for great formality and hierarchy. England was in many respects a lawless society, but it was also a litigious one. People loved law, just as they disregarded it; they could not get enough of it. It was consoling. It represented authority and tradition, even as they were being flouted. It was like listening to the king’s voice even though, if you had come to Westminster Hall on a law day, you would have found yourself amid a babble of voices.

Another Plot Twist: Section 230's Babble of Voices

And speaking of a babble of voices.... ironically, while claims that Trump was a Russian spy dominated the internet for years, some Lawlywoodland politicians (perhaps including the president himself) are calling to shackle Big Tech with cumbersome new rules that hinder the industry’s room for maneuver in the specific sphere of online content.

In effect, there’s a renewed bipartisan push to pull back tech firms’ longstanding legal immunities by sunsetting Section 230 of the Communications Decency Act. The act largely protects tech firms from being held legally responsible for third party or user content. And while both Democrats and Republicans are supporting the bill, their stated reasons for reforming the law differ. “Democrats’ pursuit of Section 230 reform has largely revolved around holding tech companies responsible for the harms their platforms allegedly cause users, including kids and teenagers…. Meanwhile, Republicans often go after Section 230 by arguing it gives large social media companies too much protection if a person, group or organization claims censorship of certain political views.”

Either way, Lawlywoodland is all astir with the idea of forcing clever tech companies to accept new rules of the game for the internet. Is the legislation that helped give birth to the digital age actually in danger? Some context is instructive—

In June 1995, two young congressmen reached across the aisle to introduce legislation that would become the defining legal protection of the internet era: Section 230 of the Communications Decency Act, which shields internet companies from liability for content created by users. Now, nearly 30 years later, another bipartisan duo hopes to drastically alter that law. With both parties aligned—and President Donald Trump seemingly interested too—they stand a better shot at actually accomplishing the task than those who’ve previously attempted it.

According to sources on Capitol Hill, Senator Dick Durbin, a Democrat, and Senator Lindsey Graham, a Republican, plan to introduce a bill that would set an expiration date of January 1, 2027, for Section 230. “If all goes according to plan, Durbin and Graham’s proposal would be the first bipartisan bill introduced in Congress that could repeal what’s often lauded as the 26 words that created the internet.”

Sounds dramatic. But Lawlywoodland is a murky place. Nothing is quite as it seems. The motivations behind the move against a cornerstone of the U.S. economy appear to be somewhat subtle and unclear. “The lawmakers say they don’t want to fully dismantle Section 230, which would have profound implications for free speech online and would devastate swaths of the tech industry. Instead, they hope the threat of an impending repeal date will push tech companies to engage in good-faith negotiations over new regulation—something the industry wouldn’t be keen to do without an ultimatum.”

Doubtless, lobbying firms are wading into the fray with glee. Franklin Square Group is one such firm that helps clients, “determine which political threats actually have teeth and which politicians are just grandstanding.” As its co-founder puts it, “Somebody that can tell them what’s real and what’s not—that’s half the battle of lobbying.”

But the Lawlywoodland fox hunt in pursuit of Big Tech doesn’t stop with the federal government. Dozens of states are also on the hunt against Section 230, with a number of state bills introduced of late. Behold—

At the same time, judges around the country have been slowly but surely chipping away at Section 230, issuing a slew of conflicting and often difficult-to-interpret rulings that make it harder for tech companies both big and small to predict their liability risks. And a deluge of pending cases regarding social media addiction will only further muddle the legal landscape, using novel legal theories that aim to sidestep Section 230 protections in an effort to hold tech giants accountable for alleged harm to children.

No wonder that defenders of Section 230 are worried. Adam Kovacevich, founder of center-left tech lobbying firm Chamber of Progress, says that, “I think most members of Congress tend to think of repealing 230 as a punishment for tech. But the reality is that without 230, platforms would either look like Disneyland, which would be a sanitized environment where every user post had to be pre-screened, or it’d be a wasteland, where essentially they never looked for anything and every platform looked like 4chan, because they didn’t want to have liability for even looking at potentially defamatory content.”

But don’t worry, says one congressional aide, “The idea would be to force them to the table, and if they don’t come to the table and agree to meaningful reform, then ultimately Section 230 would be repealed.” To which Peter Chandler, executive director of the Internet Works Association, responds by insisting, “It would be absolutely devastating.”

But in what ways and to whom? Columbia Journalism Review points out that, shorn of 230’s protections, platforms could face—

… increased liability risks for any attempts at moderation, which could result in prolonged legal battles and costly fees to defend themselves, even if they win. While major players like Meta and Google may be able to absorb these costs, it could be devastating for smaller fish in the internet pool, such as blogs, nonprofits, and newer social media sites…. Ironically, the big platforms that attract most of the negative media coverage—and thus the ire of Section 230 critics—may be in better shape to deal with the consequences of its weakening. 

Ultimately, it’s also worth wondering how AI’s continued rise and influence might one day be impacted by this storm of competing interests. Could further changes to this particular law hamper the tech economy in ways that also hinder AI’s expanding reach? Or might the reverse scenario play out by somehow invigorating Big Tech dominance?

In Lawlywoodland, the kingdom of unintended consequences, it’s hard to know.

The Verdict

In the movie, The Verdict, washed-up alcoholic Boston attorney Frank Galvin goes through life in something akin to a state of vertigo. He tries to find solid ground amid the legal and ethical bogland he finds himself wading through. In preparation for the role, actor Paul Newman insisted that Galvin’s shoes be worn down at the heels. “He’s a man who’s walked the same blocks over and over,” Newman said, “hoping they’ll lead somewhere new.”

Until the spring of 2020, we Americans had been walking through our lives in much the same manner as we had for decades. When the pandemic triggered a sudden rise of the homeshoring model, it was a major disruption that changed everything. But today, AI seems destined to be even more disruptive to the workplace and our lives. So too the Trump Revolution.

As the forces of AI and the Trump administration coalesce and promise to lead us somewhere altogether new, one big question remains—if the rule of law is an economic argument of comparative advantage, in this kind of chaotic American legal wilderness, what will it really look like for enterprises and their BPO partners to catch the AI deer and skin profit from it?

Ultimately, the chaotic nature of the U.S. legal system’s case-by-case approach could mean uneven adoption of AI—perhaps some industries will surge ahead while others get stuck in legal limbo. Still, it’s hard to imagine regulation fully stopping AI’s advance. At most, it might channel its development in unexpected directions.

However, considering the nature and complexity of ongoing legal struggles within the United States, it also seems like a fair bet that the process could become increasingly chaotic and destabilizing.

To offer just one example, just imagine if Trump administration policies double-down on incentivizing AI-enabled automation as a means of reindustrializing the American economy. On the other hand, imagine the sudden imposition of taxes on AI-driven automation, intended to fund displaced workers or slow job loss; a sort of internal tariff, a duty that seeks to protect certain categories of American labor.

In Donald J. Trump’s Lawlywoodland, kingdom of tariffs, you just never know. Right now, all that seems sure is that, in the words of Professor Paul Sracic, “Mr. Trump’s tariffs aren’t regulatory tweaks; they are transformative economic policies with far-reaching consequences.”

Image credit: Stephen Loynd’s idea, GPT Image Generator's design (March, 2025)