Free Speech Coalition v. Paxton: The Complicated Role of Technology in the Law

Background:

On June 12, 2023, the Texas legislature passed H.B. 1181, a law that would require any website whose content contains more than one-third sexual material harmful to minors to incorporate age verification methods. Before taking effect, plaintiffs sued, claiming that H.B. 1181 violated their First Amendment right to free speech. The district court ruled in favor of the plaintiffs, ruling that the age-verification requirement failed strict scrutiny, and launched an injunction. On appeal, the Fifth Circuit Court of Appeals ruled in favor of Texas, ruling that the age verification requirement only called for a rational basis review, and they vacated the district court’s injunction. The case was then appealed to the Supreme Court, which granted certiorari on July 2, 2024. The question before the court is whether H.B. 1181’s age verification requirement is subject to a rational basis review or strict scrutiny.

Technology and the Law:

What struck me most about the oral arguments was the underlying discussion about the role technology plays in the case. From discussions on age verification methods, online privacy, content filtering, and iPhones, this case felt representative of how technology and law are running at two completely different paces.

This discussion began when Free Speech Coalition’s attorney, Derek L. Shaffer, argued that age verification requirements were unnecessarily invasive of users’ privacy and that alternative, less restrictive means of regulating access to porn, such as content filtering, are far more tailored solutions that would satisfy strict scrutiny. However, this argument by Shaffer faced immediate pushback from Justice Barrett, who expressed apprehension regarding the efficacy of content filtering as an alternative to age verification. Speaking from her own experience as a mother of teenagers, she suggested that filtering technologies might not be as effective in shielding minors from explicit material, thereby questioning their viability as a less restrictive means. Many other justices echoed Justice Barrett’s concerns about technology, acknowledging the rapid evolution of technology and its impact on minors' access to online content. Justice Thomas made a concerted effort to discuss Ashcroft v. ACLU (2004) (“Ashcroft”), a case that ruled the Child Online Protection Act’s restriction on access to pornography for minors failed to satisfy strict scrutiny because it was not narrowly tailored to only apply to minors; the majority, which included Justice Thomas, believed the act was too restrictive on adults as well. However, Thomas argues that the decision was made in “a world of dial-up Internet” access, implying that the advancement of technology since 2004 has made the precedent obsolete.

Based on these discussions around the advancement of technology, it would seem that a significant block of justices are sympathetic to the Texan government’s concerns that technology has outpaced the law established in Ashcroft. As a result, they may rule that H.B. 1181 is subject to rational basis review rather than strict scrutiny, with the argument that despite age verification methods not being the least restrictive means of regulating porn, such methods are necessary as the rapid development of technology has made content filtering methods obsolete.

However, other justices, like Justice Jackson, were more hesitant to fully embrace this argument. Jackson suggested that age verification methods would place an undue burden on adults who, unlike minors, are allowed to access pornographic material. It would seem that Justice Jackson is more supportive of the Ashcroft decision, and believes strict scrutiny would be more appropriate, as the government’s desire to prevent minors from accessing pornographic content should not, in her view, override an adult’s First Amendment right. Thus, under this pro–strict scrutiny argument, age verification methods would not be properly tailored to achieving the government’s goal of regulating access to porn for minors since it would place an excessive burden on adults to access the same material.

Predictions:

By the end of oral arguments, it seemed clear to me that a general momentum had gone in favor of supporting a rational basis review for H.B. 1181. With a majority of justices expressing doubts about the effectiveness of content filtering due to rapidly changing technology, it seems like at least six or seven justices are poised to rule that rational basis review is the proper standard of review in this case, with possibly dissents only from Justices Jackson and Sotomayor. In the end, I predict this case will be decided either 7–2 or 8–1 in favor of Paxton.

Trump v. United States: Is the Outrage Warranted?

On July 1, 2024, the Court issued a highly controversial opinion on one of its most anticipated cases in the docket: Trump v. United States. The ruling, which significantly broadened the scope of presidential immunity, has sparked widespread public backlash, with many arguing that it undermines the principle of executive accountability. While these concerns are well-founded, they overlook the decision’s most flagrant flaw: its lack of constitutional grounding.

The case before the Supreme Court centered on the August 2023 indictment, which charged former President Trump with countless federal crimes related to his efforts to overturn the 2020 presidential election results. These indictments marked an unprecedented legal challenge against a former U.S. president, accusing Trump of conspiring to defraud the United States, obstructing an official proceeding, and undermining voting rights.

At the heart of the case was the question of whether a former president can be criminally prosecuted for actions taken while in office and, if so, under what conditions. The long-winded majority opinion authored by Chief Justice John Roberts established a three-tier framework: absolute immunity for acts within the president’s “conclusive and preclusive” constitutional authority, presumptive immunity for other official acts, and no immunity for unofficial conduct. Thus, this ruling effectively shields former presidents from criminal liability for a broad range of actions taken in their official capacity unless prosecutors can overcome a strong presumption against prosecution.

While Roberts made clear in his opinion that “The President is not above the law,” many fear that the ruling creates a dangerous loophole, allowing presidents to engage in misconduct under the guise of official duties. Critics argue that by granting such sweeping immunity, the Court has made it substantially more difficult to prosecute former presidents for actions that might otherwise be considered criminal, sparking concerns that future presidents could abuse their executive authority without fear of legal consequences after leaving office.

Justice Sonia Sotomayor echoes these concerns in her dissent, warning that Presidents may “feel empowered to violate federal criminal law.” Perhaps her most compelling critique, however, is her argument that the decision lacks a solid constitutional foundation, as the majority fails to ground its expansive interpretation of presidential immunity in the text or history and tradition of the Constitution. The Brookings Institute reinforces this point, asserting that “the Constitution nowhere says that a past president is by virtue of having once held that office immune from prosecution for crimes committed while in office.” If anything, the Constitution suggests the opposite. Article II explicitly states that a president may be subject to criminal prosecution after impeachment and removal, implying that former presidents can be held legally accountable for their actions. So, then, what in the Constitution grants former presidents immunity? The majority offers no clear textual or historical support for this broad protection, instead relying on speculative concerns about the separation of powers.

Moreover, as Sotomayor highlights, the “Framers [of the Constitution] clearly knew how to provide for immunity from prosecution,” implying that they knew how to grant immunity when they intended to do so. Article I, for instance, explicitly grants members of Congress protection from arrest during attendance at sessions and immunity from prosecution for speech and debate in the legislative context. Even this immunity is limited in scope and purpose, narrowly tailored to preserve legislative independence, not to shield lawmakers from accountability. The absence of any comparable constitutional protection for the president strongly suggests that no such immunity was intended. If the Framers had wanted to exempt presidents from criminal prosecution for official acts, they would have done so explicitly. Instead, the Court’s ruling fabricates a new, much more expansive form of immunity unmoored from constitutional text, history, or precedent.

As this ruling stretches the limits of executive authority, one crucial question remains: where will the Court draw the line on presidential power? Though many, including Trump and his administration, took the Trump v. United States ruling as an indication that the Court would continue deferring to the executive, recent cases seem to point to otherwise. For instance, in Department of State v. AIDS Vaccine Advocacy Coalition, the Court refused to grant the Trump administration’s emergency request to block $2 billion in foreign-aid payments, signaling the judiciary’s willingness to check executive power in certain contexts. Ultimately, this decision suggests that the Court’s approach to executive authority is not entirely compliant, leaving open questions about how it will rule on future challenges to presidential actions.

Andrew v. White

On November 20, 2001, Rob Andrew was shot and murdered. His estranged wife, Brenda Andrew, and her new partner, James Pavatt, were quickly framed as suspects in the shooting. Though Pavatt ultimately confessed to the shooting, he denied that Brenda Andrew was involved. However, the State still charged Andrew with capital murder; at the trial, the prosecution drew from extensive evidence that depicted Andrew as sexually provocative and morally depraved. Andrew’s sex life became a central issue in the trial, with prosecutors arguing that her sexual history made her a “bad wife, bad mother, and a bad woman.” Andrew was convicted of murdering her husband and sentenced to death.

Appealing the ruling, Andrew claimed that the prosecution had introduced irrelevant evidence about her sexual history, rendering the guilt and penalty phases of her trial “unfair.” By case precedent in Payne v. Tennessee (1991), Andrew argued that when “evidence is introduced that is so unduly prejudicial that it renders the trial fundamentally unfair, the Due Process Clause of the Fourteenth Amendment provides a mechanism for relief.” Citing this reasoning, she contended that evidence in her trial was prejudicial, violating the Due Process Clause. However, the U.S. Court of Appeals for the Tenth Circuit rejected the claim under the assumption that no holding of the Court clearly established a rule that erroneous inclusion of prejudicial evidence could constitute a violation of due process.

Coming before the Supreme Court in January 2024, Andrew, then the only woman on death row in Oklahoma, reappealed for federal habeas relief. To challenge the legality of one’s incarceration through federal habeas relief, the death-sentenced prisoner must show that the state court “unreasonably applied ‘clearly established Federal law, as determined by’ the Court.” In a per curiam decision, the Court vacated and remanded the ruling by the U.S. Court of Appeals of the Tenth Circuit, arguing that Payne established that the Due Process Clause can protect against the use of prejudicial evidence that renders a trial fundamentally unfair. However, by sending the case back to the lower courts, the Court did not rule on whether the precedent of Payne applies to Andrew’s case. As Justice Alito acutely highlights in his concurring opinion, acknowledging that Payne and other case law are sufficient to establish the protections of the Due Process Clause does not constitute an admission that Andrew’s case meets the “high standard” necessary. Future rulings by lower courts will determine if the trial court’s admission of evidence was so prejudicial that Andrew’s trial was fundamentally unfair.

Beyond the Court’s immediate decision, Andrew v. White invites greater debate over the stereotyping of women in the criminal justice system. The prosecution convicted Andrew under the pretense that she did not fit the norms of the ‘ideal’ woman; her clothing was not demure enough, and her behavior was too sexually promiscuous. To impose these rigid gender norms as justification for the death penalty can pose a suffocating threat to any woman who does not adhere with the traditional stereotypes of womanhood. In a legal system that lauds itself on the ideals of impartiality, incorporation of biased stereotypes is “odious…[and] pernicious in the administration of justice.” Andrew v. White marks a potential turning point, as the Court seems to be signaling that the prejudicial evidence attacking women on the basis of their nonconformity to gender norms might pose a fundamental violation to women’s constitutional rights.

On Facebook, Inc. v. Amalgamated Bank

In December 2015, The Guardian revealed that Cambridge Analytica had harvested data from 30 million Facebook users through a personality quiz created by employee Aleksandr Kogan. This data was used to create "psychographic profiles" of Facebook users initially sold to Ted Cruz's presidential campaign and later used by Donald Trump's presidential campaign. Though Cambridge Analytica agreed to delete this data in January 2016, reporters discovered in October that the firm continued using it despite its commitments. The breach remained largely contained until March 2018, when public revelations about Cambridge Analytica's continued data misuse caused Facebook's stock to plummet, harming investors alongside the users whose data was compromised.

Investors brought suit under Section 10(b) of the Securities Exchange Act of 1934 and SEC Rule 10b-5, alleging that Facebook materially misled them by characterizing data breaches as hypothetical risks in its 2016 Form 10-K when the company knew Cambridge Analytica had already improperly accessed user data. The case, Facebook v. Amalgamated Bank, was centered around a fundamental question: when does a company's characterization of a risk as hypothetical become misleading because the risk has already materialized? This question tests the boundaries of the statutory prohibition against making "any untrue statement of a material fact" or omitting material facts "necessary in order to make the statements made, in light of the circumstances under which they were made, not misleading." The Ninth Circuit ruled that investors adequately pleaded falsity, reasoning that Facebook's warnings about risks that "could" harm its business directly contradicted what the company knew when it filed its 2016 10-K. The Supreme Court granted certiorari in June 2024 and heard oral arguments in November, but just two weeks later issued a one-line order dismissing the writ as "improvidently granted" — a rare procedural move essentially admitting the Court should not have taken the case in the first place.

The Supreme Court's reticence to rule on the case became apparent during oral argument, where the Justices struggled to pinpoint the exact legal issue at stake. Facebook had portrayed the matter as a question of whether risk disclosures must include past incidents — even when they present "no known risk of ongoing or future business harm." Rather than focusing on the circuit split that Facebook emphasized in its petition for certiorari, the panel instead explored a series of hypotheticals to determine when conditional statements about future risks — if X then Y — suggest that X has not yet occurred. Justice Thomas suggested that a reasonable person would infer from Facebook's risk warnings that no data breaches had previously occurred, while Justices Sotomayor and Jackson likened Facebook's disclosures to a realtor warning about future crime risks without mentioning recent neighborhood burglaries. Even Chief Justice Roberts and Justice Kavanaugh, who seemed more inclined to support Facebook's position, found it challenging to establish a clear standard for when omitting past events renders a risk disclosure misleading. The Justices' overall uncertainty seems to have contributed to their conclusion that the case was a poor vehicle for resolving the purported circuit split that Facebook had highlighted in its petition for certiorari.

The court’s dismissal of its own certiorari reflects a guiding principle of securities law: context matters in determining whether statements are materially misleading. By declining to craft a bright-line rule, the Court effectively endorsed the case-by-case approach articulated in the Ninth Circuit's opinion, which aligned with In re Alphabet Securities Litigation in recognizing that "risk disclosures that speak entirely of as-yet-unrealized risks and contingencies and do not alert the reader that some of these risks may already have come to fruition can mislead reasonable investors." This approach requires courts to examine each statement in its full context, considering what a reasonable investor would infer from both what was said and what was omitted. The practical implication for public companies is that generic forward-looking risk factor language may constitute securities fraud when the company possesses specific internal knowledge contradicting these characterizations, particularly when those risks have already begun to materialize.

The Court's reluctance to wade into this dispute also reflects concerns about the role of the judicial branch in securities regulation. Justice Kavanaugh explicitly questioned why "the judiciary [should] walk the plank on this [. . .] when the SEC could do it," noting that “[t]he SEC knows how to write regulations that require disclosure of past events.” This judicial modesty also appeared in the Roberts court’ approach to NVIDIA Corp. et al. v. E. Ohman J:or Fonder AB et al.: like the Facebook case, the Courts initially granted certiorari before dismissing it as improvidently granted in December 2024. Ultimately, the Court left it to lower courts — and regulators — to decide when forward-looking disclosures become materially misleading.

Salesmen vs. Overtime: Preserving the Integrity of the FLSA

The Fair Labor Standards Act (FLSA) was enacted in 1938 under President Franklin D. Roosevelt as part of the New Deal to protect workers from exploitative labor practices. It established a federal minimum wage, required overtime pay for employees working more than 40 hours per week, and imposed child labor restrictions. Over time, the law has been amended to expand protections and adjust wage standards. However, the FLSA also includes several exemptions, meaning certain workers are not entitled to overtime pay. Among them are bona fide executives, agricultural workers, and outside salesmen—employees who primarily work away from their employer’s place of business. The recent Supreme Court ruling in EMD Sales, Inc. v. Carrera (2025) reaffirms this important exemption and ensures that the legal standard for classification remains consistent and reasonable.

In this case, EMD, a food distribution company, was sued by its sales representatives for failing to provide overtime pay, arguing they were misclassified under the FLSA. EMD contended that its sales representatives were outside salesmen and, therefore, exempt from overtime requirements. The legal question revolved around which standard of proof employers must meet to prove an exemption: a standard of clear and convincing evidence (meaning that the evidence leads to a firm belief in the allegations) or a standard of preponderance of the evidence (meaning that a claim is more likely true than not, requiring a much lower burden of proof). In a unanimous decision, the Supreme Court ruled that the preponderance of the evidence standard applies when an employer claims an FLSA exemption. In the opinion, delivered by Associate Justice Brett Kavanaugh, the Court reasoned that 1) the FLSA does not specify a heightened burden of proof; 2) the default standard in civil litigation is preponderance of the evidence; and 3) no constitutional rights or unusual coercive actions necessitate a stricter standard. Thus, the case was remanded for reconsideration under the correct legal standard.

Before this ruling, courts were split on the level of proof required for employers to classify workers as exempt from FLSA protections. The Fourth Circuit’s higher standard made it harder for employers to claim exemptions. The preponderance of the evidence standard, used by six other circuits, aligns with broader civil litigation practices, ensuring fairness and consistency. By ruling on the lower standard, the Supreme Court brings much needed uniformity across jurisdictions, making it easier for businesses to operate without excessive legal hurdles.

This decision reinforces that outside salesmen operate differently from traditional hourly employees. A precedent for this distinction was set in Christopher v. SmithKline Beecham Corp. (2012), where the Supreme Court ruled that pharmaceutical sales representatives qualify as outside salesmen under the FLSA and are therefore exempt from overtime pay. The Court emphasized that these employees were compensated primarily through commissions, exercised a high degree of autonomy, and performed work consistent with the traditional definition of sales. This ruling aligns with EMD Sales, Inc. v. Carrera by reaffirming that outside salesmen are distinct from hourly workers.

Unlike hourly workers, salesmen typically receive performance-based compensation such as commissions and bonuses, which often far exceed what they would earn under an hourly wage structure. Since the nature of their work is independent, flexible, and results-driven, they are not subject to the same protections as other workers. So while the FLSA’s exemption for outside salespeople may at first seem like a loophole, it is actually a necessary distinction that acknowledges the unique compensation structures and responsibilities of these roles.

This ruling preserves the original intent of the FLSA by maintaining a balanced approach to worker classification. Ensuring that sales representatives remain exempt from overtime, recognizes their earning potential and rewards their performance rather than hours worked. If commissioned salespeople were subjected to overtime requirements, the industry’s compensation model would be completely disrupted and would result in unintended consequences such as lower base salaries or reduced commission structures.

The FLSA protections affect over 140 million workers in the US, making it crucial to uphold a fair and predictable framework that benefits both employers and employees. By affirming the preponderance of the evidence standard, the Supreme Court’s decision upholds a fair and pragmatic interpretation of the FLSA. This ruling does not diminish worker protections but rather reinforces a system that has functioned effectively for decades, allowing businesses and employees alike to thrive under established compensation models. As the labor market evolves, maintaining clear and consistent standards is essential for ensuring economic stability and continued opportunities for workers in commission-based roles.

Bessent v Dellinger Re: Order Issued February 21, 2025

In what could have been the Supreme Court’s first meaningful engagement with a Trump-related appeal, Bessent v. Dellinger instead offered little judicial clarity, as the justices sidestepped substantive questions by holding the government’s application in abeyance, leaving broader legal issues unresolved. Hampton Dellinger was confirmed by the Senate to serve as the Special Counsel for the Office of Special Counsel on February 27, 2024, following a nomination from then-President Joe Biden. The Office of Special Counsel’s primary function is to protect governmental whistleblowers and safeguard against political corruption. On February 7, 2025, President Trump announced that he had fired Dellinger. Trump’s removal of Dellinger follows a familiar pattern of politically charged firings of government watchdogs, often without clear cause, undermining the independence of officials tasked with oversight. Dellinger sued the administration arguing that his firing violated 5 U.S.C § 1211(b), which states that the Special Counsel shall serve a 5 year term, and can be removed by the President “only for inefficiency, neglect of duty, or malfeasance in office.” District Judge Amy Berman Jackson issued a temporary restraining order (TRO), which restrained President Trump from firing Dellinger, effectively reinstating Dellinger as Special Counsel for the duration of the TRO (14 days). The Department of Justice immediately appealed on the Supreme Court’s emergency docket.

The petitioners in Bessent asked the Court to consider both a procedural and substantive question. First, does the Court have appellate jurisdiction over TROs, which are not generally appealable, under the All Writs Act in “light of the core executive power assertedly restrained”? Second, does 5 U.S.C § 1211(b) violate the principle of separation of powers, by unduly restricting a President’s authority? The majority answered neither question. Instead, the Court held the application in abeyance until February 26, when the TRO is set to expire. But in doing so, the Court merely kicked the can down the road and will have to answer these questions on their merits when this case eventually winds up back in the Supreme Court, presumably when District Judge Jackson rules on a preliminary injunction.

The majority’s failure to reject the application on procedural grounds is concerning. It is widely understood that TROs are not appealable, primarily because they are only in effect for 14 days—by the time briefing and arguments have occurred on the appellate TRO, the TRO would no longer be in effect. But the Trump administration is asking the Court for an exception, presumably because TROs impinge on the President’s ability to take bold and decisive action. But this could be a dangerous argument for the Court to accept. As of February 25, 2025, there are 92 pending lawsuits against the Trump administration and some of its facially lawless orders. If the Court grants the Trump administration free reign to appeal every TRO, it risks stripping District Courts of their authority to uphold the rule of law, reducing their orders to mere temporary suggestions endlessly challenged on appeal.

Justices Sotomayor and Jackson would have denied the application for TRO vacatur. Justices Gorsuch and Alito dissented from holding the application in abeyance, citing that the TRO acts as a preliminary injunction due to the special nature of the President’s executive power.

Through its substantive second question, this case has also teed up the Court to overturn Humphrey’s Executor, a 1935 case that upheld the constitutionality of “for cause” removal provisions. Conservative justices have long been chipping away at Humphrey’s Executor, such as in Seila Law LLC v. Consumer Financial Protection Bureau (2020) ruling that Humphrey’s Executor could not extend to “an independent agency led by a single Director and vested with significant executive power.” If the Roberts Court’s treatment of precedent cases like Roe (1973) and Chevron (1984) is any indication, Humphrey’s Executor could soon meet its end.

On March 1st, District Judge Amy Berman Jackson ruled in favor of Hampton Dellinger and awarded injunctive relief preventing the Trump administration from firing Dellinger on the basis of 5 U.S.C § 1211(b). There is no dispute regarding the statutory interpretation of 5 U.S.C § 1211(b), but the Trump administration instead challenged its constitutionality. The question presented was “whether it is an unconstitutional intrusion on the President’s Article II powers to say that he may remove the Special Counsel for reasons related to his performance, but he cannot do it on a whim or out of personal animus.” Unsurprisingly, the Trump administration argued that “the President of the United States must have control over the head of this small federal agency” and therefore “the President should have unfettered authority to fire him for no reason at all.” In a sixty-seven page decision, Judge Jackson methodically found that the statute is not unconstitutional and that “the elimination of the restrictions on [Dellinger’s] removal would be fatal to the defining and essential feature of the Office of Special Counsel as it was conceived by Congress and signed into law by the President: its independence.”

The Trump administration’s appeal of this District Court order is inevitable. The real question lies in how they choose to proceed. Will they follow the conventional path to the United States Court of Appeals, or will they bypass it entirely, seeking immediate intervention from the Supreme Court and Chief Justice Roberts? Equally revealing will be the speed with which the Supreme Court grants certiorari and schedules arguments. These procedural choices will serve as an early litmus test for how the Court will engage with the Second Trump administration.

On March 5, 2025, the United States Court of Appeals for the District of Columbia released a short, unsigned order to stay the District Court’s preliminary injunction. The order “gives effect to the removal of [Dellinger] from his position as Special Counsel of the U.S. Office of Special Counsel.” Briefing has been set for the expedited date of April 11, 2025 with oral arguments to follow. Dellinger is likely to appeal this stay to the Supreme Court on the emergency docket.

One day after the Court of Appeals issued a stay in the proceedings, Hampton Dellinger announced on March 6, 2025 that he would be dropping the case, citing that his odds of prevailing at the Supreme Court “are long”. As a result, the Court will have no opportunity to review the constitutionality of 5 U.S.C § 1211(b). Some may welcome Dellinger’s decision, as it prevents the Court from overturning Humphrey’s Executor and radically reshaping presidential authority. However, the Trump administration may interpret the Court of Appeals’ decision and Dellinger’s withdrawal as a green light to carry out more unlawful firings without fear of judicial intervention.