I have spent my career at the intersection of law and public discourse. My role isn’t just to provide commentary—it is to act as a strategic translator for the issues that define our era. Whether I’m serving as a neutral mediating an employment or Title IX case for clients, providing educational legal commentary on the latest in employment and workplace laws, or hosting my Legal Lens radio show and podcast, my mission remains constant: helping people resolve legal problems through the mediation and dispute resolution process, and helping educate and enlighten everyday people on the legal and policy issues that impact their everyday lives.
In my latest episode of the Legal Lens Podcast, I sat down with Attorney Deepak Gupta, founding principal of Gupta Wessler, to pull back the curtain on the nation’s highest court – the United States Supreme Court. From his “bunker” in Washington, D.C., Gupta shared why he remains an optimist even in trying times and how he successfully convinces conservative justices to rule in favor of consumers, workers, and immigrants. You can find us on Apple Podcasts, Spotify, and anywhere you get your podcasts for free. You can also listen to the full episode below:
The United States Supreme Court often feels like an impenetrable fortress of black robes and “legalese.” For many, it seems the “movie is already written”—that a 6-3 conservative majority ensures the outcome before a single brief is filed. But if you ask Deepak Gupta, one of the nation’s most prolific appellate specialists, the story of American justice is far from over. Below are the timestamps and topics covered to help you navigate our latest episode:
Key Moments & Timestamps
- [00:00:30] – Meeting at the “Shades of Mass” conference.
- [00:02:11] – Deepak’s “Why”: Inspired by Thurgood Marshall and the Civil Rights Movement.
- [00:06:36] – Civics 101: The role of the Supreme Court as the “top of the pyramid.”
- [00:08:45] – The current 6-3 conservative makeup of the Court.
- [00:12:00] – The advocacy imbalance: Why the “little guy” needs elite representation.
- [00:22:36] – Deep dive into the Ford case and the importance of jurisdiction.
- [00:28:50] – Preview of current 2026 term cases: Forced labor, NLRB, and pension funds.
- [00:32:11] – Finding hope in a time of stress for the rule of law.
Who is Attorney Deepak Gupta?
Deepak didn’t always know he wanted to be a U.S. Supreme Court specialist. Inspired by the legacy of Thurgood Marshall, he entered law school with a singular “why”: to use the law as a meaningful tool to help people. His career took a decisive turn when, as a student intern at the ACLU, he was tasked with writing a Supreme Court brief because “nobody else was available.”
“I went to law school knowing I wanted to do work that would help people and that would be in the public interest… I knew that I wanted to use the law in a way that was meaningful to help people.” — Attorney Deepak Gupta
Today, Deepak is a “repeat player” in a field dominated by large corporate firms. While most U.S. Supreme Court practitioners represent the interests of Fortune 500 companies, Gupta has carved out a specialized niche representing the “little guy.” Over the last two terms, his firm ranked in the top five for the number of arguments presented before the Court—and remarkably, their win rate outperformed many of their corporate competitors.
Understanding the “Law Docket” vs. the “Hot Button Docket”
When we see the U.S. Supreme Court in the news, it is usually centered on “blockbuster” cases involving abortion, affirmative action, or voting rights. Deepak acknowledges that while these cases are monumental, they are only part of the story. He makes a crucial distinction between the “shadow docket,” the “hot button docket,” and what he calls the “law docket.”
The law docket consists of cases that may not lead the nightly news but fundamentally shape our daily lives. These are the trending court cases that determine access to justice and economic fairness. One of Gupta’s proudest victories involved a unanimous decision in the Ford case, where he persuaded the justices that a person should be able to sue a corporation in the state where they were injured.
“We joke in our firm that… we focus on what we call the law docket, which is where the law might actually matter in the cases. It’s about legal arguments that might be able to persuade these justices.” — Attorney Deepak Gupta
High-Stakes Battles: Forced Labor and Workers’ Rights
As we move through the 2026 term, Deepak is currently at the center of several trending legal topics. His current caseload reflects the most pressing issues facing our democracy today:
- Forced Labor in Detention: Gupta is representing immigrants in a case against Geo Group, challenging the practice of putting detainees to work without pay—a victory that was recently upheld by the Ninth Circuit.
- Protecting Independent Agencies: He is representing Gwynne Wilcox in a fight against an illegal firing from the National Labor Relations Board (NLRB), exploring whether a President can fire neutral decision-makers at whim.
- Truckers and Arbitration: In Flowers Foods v. Brock, Gupta is fighting for truck drivers to have their day in court over wage claims, challenging “forced arbitration” clauses that strip workers of their legal recourse.
“There are things that creative lawyers and dedicated lawyers can do to make a difference even in a judicial environment that may be hostile… that doesn’t mean that there isn’t something we can accomplish.” — Attorney Deepak Gupta
A Message of Hope for the Future of Democracy
It is easy to look at the current political climate and feel a sense of horror. Deepak isn’t blind to the stress the rule of law is under, but he chooses to be a fighter. He reminds us that words matter. The ability to write an argument that a President or a multi-billion-dollar corporation must respond to is an incredible power.
“You can write down words on a piece of paper and the person on the other side, whether it’s the president or a big corporation, they have to respond. And that’s incredibly powerful.” — Attorney Deepak Gupta
Whether you are a law student looking for your place in history or a citizen concerned about the future, Gupta’s message is clear: join the fight. The story isn’t over yet.
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My conversation with Deepak offered insights that help shape the national dialogue during this time of great upheaval. Whether we are discussing justice and the rule of law or the nuances of trending cases, the goal remains the same: Bringing Law to Light by helping educate the everyday person on the legal and policy issues that impact their daily lives.
I have dedicated my career to helping litigants resolve their legal disputes through the mediation and dispute resolution process, and by helping dissect the legal issues that shape our public discourse and workplace dynamics, whether it be as a radio and podcast show host, or as a legal analyst in the news. . My mission as the host of the Legal Lens radio show and podcast is to empower you with objective, expert-driven insights born from years of practice at the intersection of law and society.
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Angela’s Other Work
Learn more about my book – The Workplace Transformed: 7 Crucial Lessons from the Global Pandemic – here – https://angelareddock-wright.com/book/.
Learn more about my work as an employment and Title IX mediator here Angela J. Reddock-Wright | Signature Resolution and on LinkedIn@Angela J. Reddock-Wright, Esq., AWI-CH.
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This communication is not legal advice. It is educational only. For legal advice, consult with an experienced employment or civil rights law attorney in your state or city.