Inside Gregory Dubinsky’s Legal War Room: Trials, Appeals, and Constitutional Battles

Gregory Dubinsky doesn’t just defy expectations – he rewrites them. With a rare resume that includes clerkships at all three levels of the federal judiciary, culminating with Justice Anthony Kennedy at the U.S. Supreme Court, Dubinsky has built a litigation practice as versatile as it is formidable.

At Holwell Shuster & Goldberg, Dubinsky's not confined to one courtroom or one style of advocacy. He thrives in both trial and appellate arenas. He seamlessly switches from cross-examinations to constitutional arguments, from complex commercial disputes to precedent-setting appeals.

“I knew I didn’t want to limit myself,” Dubinsky says. “Taking on a mix of roles – serving as plaintiff and defense counsel, litigating trial and appellate matters – has made me a better lawyer.”

His clients span industries and issues – from defending Visa in sprawling multidistrict class actions to representing the National Basketball Association in the first antitrust suit the league had faced in a decade to submitting multiple Supreme Court briefs on behalf of Members of Congress on hot-button statutory issues. Whether navigating high-stakes commercial litigation or shaping constitutional doctrine, Dubinsky brings strategic clarity and intellectual firepower to every matter.

Dubinsky’s versatility isn’t just tactical – it’s transformative. He has secured billion-dollar dismissals under the Video Privacy Protection Act, authored amicus briefs that have been cited by Supreme Court justices and state courts, and shaped doctrine across multiple areas of law.

One of Dubinsky’s great strengths lies in his ability to navigate the intricate details of complex legal issues while crafting clear, compelling arguments that resonate with judges and juries alike. He parses dense statutes and distills complicated disputes into straightforward narratives, making the law accessible and persuasive. He’s fueled by the work – and driven by something deeper. After securing a crucial appellate victory for a pro bono client, she told him: “This makes me feel like justice is alive.”

For Dubinsky, that’s the point. The law isn’t just a puzzle to be solved – it’s a force for real justice, in real lives.

“That’s our task as lawyers,” says Dubinsky. “To make justice alive for our clients.”

Lawdragon: Can you describe for our readers the mix of work you do within your practice?

Gregory Dubinsky: I represent both plaintiffs and defendants in high-stakes disputes across many different areas of law. On the plaintiffs’ side, I am currently lead counsel in an antitrust action against a dominant hospital system in the Midwest, a case that has major implications for the healthcare market. I have previously tried a $700M civil antitrust case against News Corp., which settled favorably during jury deliberations, and a securities-law arbitration that resulted in an eight-figure settlement.

I knew I didn’t want to limit myself to only trial or only appellate work. I enjoy both getting into the facts and crafting creative legal arguments, so I have intentionally built a diverse practice.

On the defense side, I am a senior member of the Holwell Shuster & Goldberg team acting as national lead trial counsel for Visa in the defense of multidistrict antitrust class actions and opt-out litigation asserted by the world’s largest retailers. I have defended the National Basketball Association on multiple occasions, including in an antitrust action concerning player-agents and in a federal suit raising RICO and trademark infringement issues. And I recently served as lead counsel to IBM and Rumble in cases alleging violations of the Video Privacy Protection Act, securing dismissals on their behalf.

Beyond my commercial litigation practice, I have represented parties in various disputes involving political figures and constitutional questions. I served as lead counsel to a former governor of New York in a separation-of-powers suit against the New York State Commission on Ethics and Lobbying in Government, which had charged the former governor with ethics violations related to a book deal. And I recently filed a U.S. Supreme Court amicus brief for Members of Congress in a case that promises to define the scope of the expropriation exception to Foreign Sovereign Immunities Act immunity. I’ve also submitted Supreme Court briefs for Members of Congress on issues involving the interpretation of anti-terrorism statutes, and Justice Kagan quoted an amicus brief I authored on behalf of a bipartisan group of state legislators in her separate opinion in a partisan gerrymandering case.

In the course of my work, I’ve delivered oral arguments in various U.S. Courts of Appeals and federal district courts, the highest courts of New York and Connecticut, and in binding arbitration.

LD: That’s impressive. How did you first become interested in developing this type of practice?

GD: After clerking at all three levels of the federal judiciary, from the district court up through the Supreme Court, I knew I didn’t want to limit myself to only trial or only appellate work. I enjoy both getting into the facts and crafting creative legal arguments, so I have intentionally built a diverse practice. I’ve also found that taking on a mix of roles – serving as plaintiff and defense counsel, litigating trial and appellate matters – has made me a better lawyer. For example, my appellate background helps me build the most effective record for appeal when I’m litigating at trial.  And knowing the ins and outs of trial work is very helpful in making effective, practical arguments on appeal.

LD: Can you describe a recent matter that you’ve handled?

GD: I have recently achieved dismissals of putative class actions against both IBM and Rumble that alleged violations of the Video Privacy Protection Act (VPPA). In the IBM case, the putative class comprised users who watched videos on The Weather Channel’s website, which IBM previously owned. The plaintiffs alleged that users’ personally identifiable information was disclosed to third-party marketing partners in violation of the VPPA. In the Rumble action, plaintiffs alleged a VPPA violation based on disclosure of subscribers’ personal information to Facebook. The potential impact of VPPA suits is massive, as plaintiffs’ lawyers seek $2,500 per video viewed on these websites over a multi-year period – aggregating to billions of dollars of theoretical exposure.

Justice Kennedy instilled in me and my fellow clerks the understanding that constitutional liberty does not reside in our DNA – we need to learn and teach others the critical importance of our constitutional freedoms and checks and balances.

LD: Was there an early experience or mentor who really helped shape the course of your professional life?

GD: Justice Kennedy instilled in me and my fellow clerks the understanding that constitutional liberty does not reside in our DNA – we need to learn and teach others the critical importance of our constitutional freedoms and checks and balances. Justice Kennedy noted that every generation must relearn those lessons, and that we all play our part in upholding our ideals. On a more personal note, “the Boss” (as we affectionately called him) was a model for how one can work at the highest levels of the legal profession and grapple with the most difficult legal questions while maintaining warm collegiality. I think of one Friday evening during a busy period, when I was on the phone with Justice Kennedy and asked him if anything more needed to be done that night. He encouraged the clerks to leave and enjoy the evening – of course, we kept working!

LD: Is there a matter or client in your career that stands out as formative for you?

GD: I represented a victim of sexual assault in prison and secured reversal in the 9th Circuit of the dismissal of her claims. When that decision came down, my client told me something I’ll never forget: “This makes me feel like justice is alive.” That’s our task as lawyers – to make justice alive for our clients.

LD: How would you describe your style as a lawyer?

GD: I’m relatively cerebral and love the law, but I also enjoy a good, clean fight about the facts. I make a particular effort to distill complex arguments into their simplest form, which is what is needed to maximize the likelihood of convincing the judge or jury.

LD: There are many high-quality firms out there. What makes Holwell Shuster & Goldberg unique?

GD: We distinguish ourselves by being real “lawyer’s lawyers” – people who genuinely thrive in the law – and in how we treat each other, by prizing collaboration and collegiality. The work is intense, with a lot of time in the trenches, so it’s important to trust and respect the lawyers with you. One of the most rewarding aspects of the job is the bonds we form with each other and with our clients.

LD: If you weren’t a lawyer, what would you be doing now?

GD: I love the creative freedom involved in imaginative fiction, like sci-fi. If I weren’t practicing law, one fantasy is to have been a writer.