Neal Katyal’s Pro Litigation Moves: Winning Supreme Court Cases

In an era defined by rapid societal shifts and deeply polarized public discourse, the Supreme Court of the United States stands as a pivotal battleground where the future of our nation’s laws is forged. Every term, the justices weigh cases that touch the very fabric of American life, from digital privacy and economic regulation to fundamental civil liberties and human rights. The stakes are astronomically high, and the path to victory demands not just unparalleled legal acumen, but an almost alchemical blend of strategic insight, persuasive storytelling, and an unwavering grasp of precedent. It’s a theater where only the most brilliant legal minds dare to tread, transforming complex legal theory into actionable outcomes that reverberate for generations.

Among these elite practitioners, few possess the formidable reputation and track record of Neal Katyal. A distinguished Georgetown Law professor, former Acting Solicitor General of the United States, and an attorney who has argued an astounding number of cases before the Supreme Court – often against daunting odds – Katyal has become synonymous with crafting winning arguments at the highest echelons of American jurisprudence. His approach isn’t merely academic; it’s a dynamic, almost ‘pro-litigation’ philosophy that blends deep constitutional understanding with a keen eye for real-world impact and ethical advocacy, pushing the boundaries of legal possibility in our complex, interconnected world.

We sit down with Neal to dissect the moves that define Supreme Court success. This conversation isn’t just a look behind the curtain of high-stakes legal battles; it’s an exploration into the art of persuasion, the critical importance of a nuanced legal strategy, and the innovative ways top advocates navigate the complexities of constitutional law in the digital age. Prepare for practical insights, fresh perspectives on legal strategy, and a deeper understanding of what it truly takes to influence the course of American law.

What, then, are the foundational principles that truly differentiate a winning Supreme Court argument from one that falls short?

Neal Katyal’s Pro Litigation Moves: Winning Supreme Court Cases

The legal landscape is shifting at warp speed, redefined by algorithms, data streams, and decentralized networks. As a young digital lawyer, steeped in the promise and peril of this new frontier, I’m constantly seeking wisdom from those who have navigated the most complex legal battles. Few have done so with the consistent brilliance of Neal Katyal, whose Supreme Court arguments have shaped constitutional law and administrative practice for decades. But how do the ‘pro moves’ of a Supreme Court litigator translate to the intricate, often uncharted, territories of AI ethics, data governance, and digital rights? I had the opportunity to ask him exactly that, probing for the practical insights that can empower individuals, startups, and even established tech giants in this volatile digital era.

Interviewer: Mr. Katyal, your career is a masterclass in navigating the highest legal stakes, often involving intricate constitutional questions. As we see technology rapidly outpace traditional legal frameworks—think AI deepfakes challenging defamation, or blockchain’s inherent anonymity clashing with regulatory demands—what foundational lessons from your Supreme Court work apply to the emerging challenges of AI, data, and decentralized systems?

Neal Katyal: It’s a fascinating parallel. At its core, Supreme Court litigation, much like navigating the digital legal frontier, is about understanding underlying principles. Whether it’s free speech in the context of online content moderation, due process in algorithmic decision-making, or privacy in a world of pervasive data collection, the challenge is often the same: fitting new facts into old legal boxes. My approach always starts with identifying the core values at stake. Is it individual liberty? Public safety? Economic innovation? The framers didn’t envision neural networks, but they did build a framework for protecting fundamental rights against new forms of power, whether governmental or, increasingly, corporate. For instance, in Packingham v. North Carolina, where we argued for the First Amendment rights of a registered sex offender to access social media, the principle was clear: the internet is the modern public square. The medium changes, but the constitutional imperative to protect open discourse remains. The ‘pro move’ here is to distill the novel into the foundational, identifying the constitutional bedrock upon which to build your argument, even if the technology seems utterly alien.

Interviewer: Given the sheer scale and speed of data collection and algorithmic decision-making, where do you see the most significant ‘legal blind spots’ for individuals and even sophisticated tech companies? What common mistakes, from a litigation perspective, are being made in this evolving landscape?

Neal Katyal: One of the biggest blind spots, surprisingly, isn’t always about novel legal theories but about basic contract and consent. Individuals click ‘accept’ on terms of service without reading, effectively signing away rights to their data or even their digital creations. On the corporate side, I’ve seen companies get into hot water because they designed systems for efficiency, not for legal defensibility or ethical compliance. They often overlook the chain of consent for data, or they fail to audit their AI models for bias before deployment, leading to discriminatory outcomes that invite class-action lawsuits or regulatory fines. A real-world example? The growing body of cases around AI-driven hiring tools that inadvertently discriminate against protected groups. The mistake isn’t necessarily malice, but a lack of foresight: neglecting to build legal and ethical reviews into the design process, not just as an afterthought. From a litigation standpoint, if you can’t demonstrate transparent data provenance, clear consent pathways, and robust fairness audits, you’re building a house on shaky ground. The legal system, even if slow, will catch up to fundamental injustices.

Interviewer: We’re witnessing a global scramble for AI regulation, from the EU’s AI Act to various state-level privacy laws like California’s CCPA. How are these nascent legal responses, or even the threat of them, beginning to alter public behavior or corporate strategy in the tech space? Are we seeing a shift towards more proactive ethical design, or more reactive compliance?

Neal Katyal: It’s a complex mix, and frankly, we’re seeing both. The specter of significant fines and mandatory transparency is undeniably pushing many corporations towards more reactive compliance—they’re hiring legal teams, updating policies, and running audits to avoid penalties. However, for genuinely forward-thinking companies, and indeed for many startups, there’s also a growing recognition that ‘ethical AI’ or ‘privacy by design’ isn’t just a regulatory burden, but a competitive advantage and a brand differentiator. Consumers, increasingly aware of their digital footprints, are starting to demand more transparency and control. You see this reflected in a subtle but measurable shift in public behavior; people are more likely to scrutinize privacy policies, use privacy-preserving tools, or even opt out of data-hungry services. Studies, like those from the Pew Research Center, show a significant increase in public concern over data privacy. This public demand, coupled with regulatory pressure, is fostering a slow but steady shift towards a more proactive integration of ethics and law into the very architecture of technology. It’s a societal feedback loop: public concern drives regulation, which in turn influences corporate strategy, ultimately shaping user experience.

Interviewer: For the next generation of innovators and digital citizens, understanding their rights in this complex digital ecosystem is paramount. From your vantage point, what’s one critical piece of advice on how to approach digital contracts, data usage agreements, or even the terms of service that govern so much of our online lives?

Neal Katyal: The most critical piece of advice, which many find tedious but is absolutely vital, is to read and understand the terms. I know, it sounds elementary, but the sheer volume and complexity often lead to a blanket ‘accept.’ However, these are legally binding contracts that dictate what can be done with your data, your content, and even your digital identity. My ‘pro move’ here is to treat them like any other significant contract. If it’s a service you rely on heavily, or one that deals with sensitive personal information, take the time to understand the key provisions: what data they collect, how it’s used, who it’s shared with, and crucially, how you can revoke consent or exercise your deletion rights. Don’t be afraid to use tools or browser extensions that summarize these terms, but always verify the core details. For innovators, this means drafting terms that are not only legally sound but also clear, accessible, and fair. Trust is built on transparency, and confusing legalese erodes that trust instantly. Remember, a contract isn’t just a legal shield; it’s a reflection of your commitment to your users.

Interviewer: That point about reading and understanding terms, though seemingly simple, reveals so much about the asymmetry of power in the digital world. It’s not just about what laws exist, but about how effectively individuals can exercise their rights within those frameworks.

The digital world, for all its dazzling promise of connection and innovation, often feels like a sprawling, untamed frontier. We’ve built towering cities of data, forged currencies out of code, and granted intelligence to machines, yet the legal and ethical maps for navigating this new landscape are still being sketched, often in the frantic aftermath of a new crisis. It’s in these moments of rupture, when technology outpaces our collective wisdom, that the tension between what’s possible and what’s permissible becomes blindingly clear.

# Part 1 — The Digital Dilemma: When Reality Fractures

Just last year, the internet was ablaze with outrage over deepfake images of prominent public figures. It wasn’t just a matter of photoshopped memes; these were sophisticated, hyper-realistic fabrications, often non-consensual and sexually explicit, disseminated across platforms at the speed of light. The technology, once a niche tool for special effects, had democratized malice, making it terrifyingly easy for anyone with ill intent to digitally violate, defame, or exploit another. What struck me most acutely, beyond the immediate harm to the individuals, was the profound sense of helplessness. Imagine seeing your face, or the face of someone you know, plastered onto a digital lie, completely outside your control, eroding trust and reality itself. This wasn’t just a fleeting scandal; it was a potent demonstration of how rapidly AI can weaponize information, blurring the lines between truth and deception, and exposing gaping holes in our societal and legal defenses.

This particular incident, while vivid, is merely a symptom of a larger systemic challenge. We’ve witnessed similar digital tremors across various domains:
Data Leaks & Breaches: From the infamous Equifax breach in 2017 to countless smaller, yet devastating, corporate data exposures, sensitive personal information—financial records, health data, even deeply intimate details—has become currency in a shadow economy. These incidents aren’t just technical failures; they’re invasions of our digital selves, leaving individuals vulnerable to identity theft, fraud, and profound emotional distress. I remember counseling a friend through the aftermath of a minor data leak from a health app; the anxiety and feeling of exposure were palpable, far beyond the immediate financial concerns.
NFT Fraud & Copyright Confusion: The meteoric rise of Non-Fungible Tokens (NFTs) promised to democratize art and empower creators through blockchain’s immutable ledger. Yet, it also unleashed a torrent of copyright infringement. Artists have woken up to find their work minted and sold as NFTs without their permission, often by anonymous actors exploiting the nascent, unregulated nature of web3. The very decentralization that was supposed to protect ownership also made enforcement a global game of whack-a-mole, highlighting the clash between traditional IP law and novel digital assets.
Algorithmic Bias & Discrimination: Beyond explicit deepfakes, more insidious forms of harm emerge from the algorithms that increasingly govern our lives. AI systems used in hiring, loan applications, criminal justice, and even healthcare have been shown to perpetuate and amplify existing societal biases, often due to biased training data or flawed design. A study cited by the Stanford Cyber Policy Center highlights how certain facial recognition systems disproportionately misidentify people of color, raising grave concerns about fairness and equity in an increasingly automated world. These biases aren’t always malicious, but their impact can be deeply discriminatory, denying individuals opportunities or unjustly scrutinizing them, often without their knowledge or recourse.
Online Privacy Scandals & Surveillance Capitalism: The Cambridge Analytica scandal was a watershed moment, revealing how personal data, harvested from social media, could be weaponized for political manipulation. Yet, the underlying mechanisms of “surveillance capitalism,” where our every click, scroll, and interaction is tracked, monetized, and used to shape our behaviors, persist. The constant negotiation of privacy settings, the deluge of “accept cookies” banners, and the feeling of being perpetually watched by invisible algorithms underscore a fundamental shift in our relationship with technology and our expectation of digital autonomy. The lines between informed consent and coerced acceptance become increasingly blurred.

These dilemmas are not isolated incidents; they are interconnected threads in a rapidly evolving tapestry of digital existence. They force us to confront uncomfortable questions: Who is responsible when AI harms? How do we protect individual rights when data transcends borders? Can legal frameworks, designed for a physical world, truly govern the ethereal domains of code and bits? The answer, increasingly, is not without significant re-architecture and a bold reimagining of justice.

# Part 2 — Legal & Ethical Framework: Playing Catch-Up

The law, by its very nature, is a slow beast. It evolves through precedent, societal consensus, and deliberate legislative processes. But the digital realm moves at warp speed. This fundamental mismatch creates the “legal lag” we currently experience, where existing laws strain, often unsuccessfully, to address novel digital harms.

Let’s dissect this further:

Existing Laws: A Patchwork Under Strain

Defamation and Intellectual Property (IP): In the case of deepfakes, traditional defamation laws can apply, but proving intent, identifying anonymous perpetrators across jurisdictions, and demonstrating material harm in the rapid dissemination cycle is incredibly challenging. For NFT fraud, copyright law should protect creators, but the decentralized nature of blockchain makes enforcement complex, often requiring individual artists to pursue costly legal action against unknown parties, navigating a global web of differing IP regimes. The EFF has consistently highlighted the challenges of applying traditional copyright to digital content, especially with issues like fair use in generative AI.
Privacy Laws (GDPR, CCPA): The European Union’s General Data Protection Regulation (GDPR) stands as a global gold standard for data protection, granting individuals significant rights over their personal data. Similarly, the California Consumer Privacy Act (CCPA) provides robust protections in the U.S. These laws provide crucial frameworks for consent, data access, and the right to be forgotten. However, they primarily address data handling rather than the specific harms arising from AI’s autonomous decision-making or synthetic media. While GDPR’s principles of fairness and transparency are relevant, applying them directly to the opaque “black box” nature of some AI systems, where it’s difficult to discern how a decision was reached, remains a significant hurdle. How do you exercise your “right to explanation” when the explanation itself is a complex interplay of billions of parameters?
Consumer Protection & Product Liability: When an AI system in an autonomous vehicle causes an accident, or an algorithmic trading platform loses millions due to a glitch, the principles of product liability or negligence might apply. But determining the “manufacturer” of an AI—is it the developer of the algorithm, the provider of the training data, or the end-user who deployed it?—is a legal Gordian knot. The OECD’s work on responsible AI governance consistently points to the need for clarity in accountability frameworks.

1. Jurisdictional Headaches: The internet knows no borders, but laws are inherently territorial. A deepfake created in one country, hosted on a server in another, and viewed by victims globally creates a jurisdictional nightmare. Who has the authority to prosecute? Which country’s laws apply?
2. Technological Opacity: The “black box problem” of advanced AI systems makes it difficult to understand why an algorithm made a certain decision or how it learned a particular bias. This opacity clashes directly with legal demands for transparency, due process, and explainability.
3. Anonymity & Attribution: Blockchain’s pseudo-anonymity and the ease with which bad actors can hide behind VPNs and proxies make identifying and prosecuting wrongdoers incredibly difficult, often rendering legal victories Pyrrhic.
4. Defining “Harm”: While physical harm is clear, digital harm can be intangible yet devastating—reputational damage, emotional distress, algorithmic discrimination that denies opportunities. Our legal systems are still grappling with how to adequately quantify and compensate for these novel forms of injury.
5. Pace of Innovation vs. Legislation: As soon as a law is drafted to address a specific tech challenge, the technology itself has often evolved two steps further, creating a perpetual game of catch-up.

Government Action: The European Union AI Act is a groundbreaking effort, adopting a risk-based approach to AI regulation. It categorizes AI systems based on their potential to cause harm, imposing stricter requirements (e.g., transparency, human oversight, conformity assessments) on “high-risk” applications like those used in critical infrastructure, law enforcement, or employment. This is a crucial step towards proactive regulation rather than reactive litigation. In the US, the White House Executive Order on AI emphasizes safety, security, and trust, pushing federal agencies to develop standards and address risks while promoting innovation. States like California are also exploring their own AI-specific legislations.
Tech Giants’ Self-Regulation: Many platforms have developed sophisticated content moderation policies, AI ethics principles, and transparency reports. However, these efforts are often inconsistent, criticized for their selective enforcement, and ultimately subject to commercial pressures rather than independent public oversight. Companies like Google, Meta, and OpenAI are investing heavily in “responsible AI” teams, yet the effectiveness and true independence of these initiatives are often debated. Their responses often feel like a tightrope walk between innovation, profit, and public responsibility.
Advocacy & Academia: Organizations like the EFF continue to champion digital rights, pushing for stronger privacy laws and advocating against government overreach. Academic institutions like the Stanford Cyber Policy Center are at the forefront of researching AI ethics, governance, and the intersection of technology and democracy, providing crucial intellectual groundwork for policy development. These bodies play a vital role in shaping public discourse and informing legislative efforts.

While responses are emerging, the journey is long. The current framework is a complex, often contradictory, beast of old laws stretched thin, new laws taking shape, and private governance filling the gaps—often imperfectly.

# Part 3 — The Future & Actionable Insight: Building a More Resilient Digital Justice System

Navigating this evolving digital landscape requires more than just reactive fixes; it demands a proactive, multi-faceted approach that intertwines policy innovation with ethical design and robust user empowerment. As someone immersed in this space, I see immense potential for a more just and equitable digital future, provided we embrace a spirit of critical construction.

1. Policy Innovation: Adaptive, Global, and Human-Centric

The future of digital law must be fluid and adaptive. We need frameworks that can evolve without constant legislative overhaul, perhaps through regulatory sandboxes, agile policy-making, or sunset clauses that force periodic review.
International Cooperation: The internet is global; our laws must aspire to be, too. Organizations like the OECD are vital for fostering international dialogue and harmonizing approaches to AI governance, data flows, and digital taxation. We need more multilateral treaties that establish baseline standards for data protection and AI accountability, mitigating jurisdictional arbitrage.
Focus on TAI (Transparency, Accountability, Explainability): For AI, TAI must become non-negotiable. This means demanding not just what an AI does, but how it does it. This includes requirements for impact assessments, independent audits of AI systems (especially high-risk ones), and clear attribution for AI-generated content (e.g., watermarking deepfakes). The EU AI Act is a great starting point, but its principles need to be universally adopted and rigorously enforced.
Data Portability & Interoperability: Empowering users means making it easier for them to move their data between platforms. This fosters competition and reduces the lock-in effect of tech giants, giving individuals more control and making platforms more accountable. This requires legal mandates for open APIs and standardized data formats.
Digital Commons & Public Interest AI: We should explore mechanisms for funding and developing AI systems that serve the public good, perhaps as open-source utilities, rather than solely being driven by corporate profit motives. This can help mitigate algorithmic bias and ensure equitable access to beneficial AI.

2. User Rights Awareness: Empowering the Digital Citizen

Legal frameworks are only as effective as citizens’ awareness of their rights. Digital literacy isn’t just about knowing how to use software; it’s about understanding the invisible legal and ethical machinery beneath the surface.
Beyond “I Agree”: We need to educate individuals to move past blindly clicking “accept” on terms and conditions. Simplified summaries, standardized consent forms, and intuitive privacy dashboards can help users make informed choices. This also means understanding what data is being collected, how it’s being used, and who benefits.
Knowing Your Digital Rights: Everyone should have a basic understanding of their data protection rights (e.g., the right to access, rectify, or erase personal data), how to identify and report deepfakes or misinformation, and where to seek recourse for algorithmic discrimination. The EFF provides excellent resources for understanding these rights.
Critical Media Literacy: In an age of synthetic media and rampant misinformation, the ability to critically evaluate digital content is paramount. This requires investment in education that equips individuals to discern truth from fabrication, understand algorithmic manipulation, and recognize online scams.

The most effective legal interventions will be those that are baked into the technology itself, not simply layered on top.
Privacy by Design & Ethics by Design: These aren’t just buzzwords. They mean integrating privacy and ethical considerations from the very inception of a product or service, rather than as an afterthought. This includes minimizing data collection, anonymizing data where possible, building in robust security, and designing AI systems for fairness and transparency.
“Human in the Loop” Design: For critical AI applications, maintaining human oversight and intervention points is crucial. Algorithms can augment human decision-making, but they should not completely replace human judgment, especially in sensitive areas like justice, healthcare, or employment.
Auditable & Explainable AI: Developers must prioritize creating AI systems that are auditable, allowing third parties to scrutinize their performance, identify biases, and verify their compliance with ethical guidelines. This includes documentation of training data, model architectures, and decision-making processes.

4. Emerging Digital Justice Movements: Grassroots for a Better Future

The push for a more just digital world isn’t confined to legislative halls. It’s happening at the grassroots level, in activist communities, open-source projects, and citizen collectives.
Algorithmic Justice Leagues: Groups campaigning against biased algorithms are gaining traction, demanding accountability from both developers and deployers of AI.
Decentralized Autonomous Organizations (DAOs) for Governance: While nascent, some believe DAOs could offer new models for self-governance in digital communities, allowing for more transparent, democratic decision-making around shared digital assets and platforms.
* Open-Source Legal Tools: Developers and legal professionals are collaborating to create open-source tools and resources that simplify legal compliance, help users understand their rights, and even assist in legal redress for digital harms.

The digital revolution is far from over, and with it, the legal and ethical landscape will continue to shift. This is a period of immense challenge but also unparalleled opportunity. The tension I feel—a blend of cautious optimism and moral urgency—stems from the understanding that our choices now will shape the very fabric of future societies. We are not just drafting laws for technology; we are architecting the future of human rights and dignity in an increasingly automated and interconnected world. It’s a grand, complex undertaking, and one that demands our collective, informed, and ethically grounded engagement.