Host Jan Baran welcomes back Josh Gerstein, Senior Legal Affairs Reporter for Politico, for a comprehensive review of the litigation landscape surrounding the Trump administration. They dive into the Supreme Court's increasingly prominent "shadow docket" and how it has become essential for advancing presidential agendas through executive action rather than legislation.

The conversation covers major legal flashpoints including immigration enforcement cases, National Guard deployments in California, Oregon, and Illinois, and the administration's removal of officials from independent agencies. Josh and Jan explore the unprecedented criticism of the Supreme Court by lower court judges, growing concerns about judicial security, and the tension between executive power and judicial review.

They also preview significant upcoming cases, including Louisiana v. Callais on voting rights and race-conscious redistricting, and a potentially landmark tariffs case with broad implications for the balance of power between the executive and legislative branches. The discussion highlights how recent Senate confirmation process changes could reshape federal agencies and examines the legal doctrine of the "Unitary Executive."

About Josh Gerstein

Josh Gerstein is Politico’s Senior Legal Affairs Reporter. Gerstein covers the intersection of law and politics, including Special Counsel Robert Mueller’s investigation of President Donald Trump and his associates, as well as ensuing counter-investigations into the origins of the FBI’s initial inquiry into the Trump-Russia saga. While not a lawyer, Gerstein spent more time in courtrooms and reading legal pleadings than many members of the bar.

For more than a decade, he has taken Politico readers inside the most celebrated political trials of our era, involving figures like former Sen. John Edwards (D-N.C.), former White House counsel Greg Craig, longtime Trump confidant Roger Stone and former Trump campaign manager Paul Manafort.

Gerstein also reports on the Justice Department and legal controversies, including Supreme Court showdowns over same-sex marriage and Obamacare, all of the recent Supreme Court nominations, criminal justice reform and battles over executive privilege. Gerstein attended Harvard College and received a bachelor’s degree, magna cum laude, in government.

Host Jan Baran sits down with Coinbase Chief Policy Officer Faryar Shirzad for an educational and illuminating deep dive into cryptocurrency's intersection with law and politics. Faryar, whose journey from Iranian diplomat's son to White House advisor to Goldman Sachs executive led him to crypto's frontier, breaks down the complex technology in refreshingly accessible terms. He explains how the recently passed Genius Act creates the framework for dollar-backed "stablecoins" - essentially digital dollars that can transfer peer-to-peer without traditional banking intermediaries - and why this represents the next evolution of the internet's promise to eliminate middlemen.

The conversation reveals crypto's surprising political transformation from niche technology to major electoral force. Faryar details how Coinbase helped build the largest political operation any industry has ever assembled, mobilizing 2.4 million advocates through “Stand with Crypto” and strategic Super PAC spending to combat what he describes as the prior administration's "disgraceful" targeting of crypto users. With 60% of crypto advocates being Democrats but 54% voting for Trump in 2024, the crypto voter bloc has emerged as a genuinely bipartisan political force that could reshape future elections - making this episode essential listening for anyone trying to understand where money, technology, and politics intersect in modern America.

About Faryar Shirzad

Faryar Shirzad is Chief Policy Officer at Coinbase, where he leads the company’s
engagement with policymakers around the world and has become a trusted source for thought leadership in the global crypto policy space. Under Faryar’s leadership, Coinbase has become a driver of crypto-regulation discourse in the U.S. He oversaw the creation of Coinbase’s Digital Asset Policy Proposal (or dApp), which laid out a fit-for-purpose regulatory framework for the rapidly-emerging industry and was recognized as “a dramatic shift from current policy in the United States”, sparking an ongoing conversation on how crypto should be regulated while safeguarding American innovation.

Before joining Coinbase, Faryar was Global Co-Head of Government Affairs at Goldman Sachs. He has served as counsel to the highest levels of the U.S. government, including as deputy national security advisor for international economic affairs for President George W. Bush. In that role, he served as The President’s personal representative to the G-8 (the “G-8 Sherpa”). Prior to his time in the White House, Faryar was assistant secretary for import administration at the U.S. Department of Commerce and international trade counsel to the U.S. Senate Committee on Finance. Earlier in his career, he practiced law in Washington, DC. Faryar earned a JD from the University of Virginia School of Law, a MPP from the John F. Kennedy School of Government at Harvard University, and a BS from the University of Maryland, College Park.

Jan Baran speaks with Artificial Intelligence (AI) legal expert. lawyer and teacher, Oliver Roberts, to speak about AI, its birth, its forms, and how people have historically used and are currently using the ever-changing technology. They discuss further about how AI has changed the way lawyers practice, how the courts are using it, what questions clients are asking in RFPs related to technology, and why the big law firms are investing in AI.

There are plenty of upsides to using AI; but what is “AI hallucination?” Old school legal tech companies are incorporating advanced AI and new AI legal products are being promoted throughout the industry; however, any information collected through AI still requires lawyers and others to check for any false or misleading information. Spoiler Alert: Using AI may be quicker a way to research or write initially, but the AI hallucination rate can be high.

Oliver also discusses recent attempts to regulate AI, including an effort at the Federal Election Commission.

About Oliver Roberts

Oliver Roberts is an Adjunct Professor of Law at Washington University in St. Louis School of Law and Co-Director of the WashU Law AI Collaborative. He is also Co-Head of the AI Practice Group at Holtzman Vogel law firm, Editor-in-Chief of the AI & the Law publication at The National Law Review, and the Founder and CEO of Wickard.ai.

Oliver regularly lectures on AI at law schools throughout the United States and internationally. His recent teaching includes the course “AI & the Practice of Law” at WashU Law, the nation’s first required AI law school course at Case Western Reserve School of Law, and the first legal AI education program at Addis Ababa University School of Law in Ethiopia.

Oliver graduated from Harvard Law School and Villanova University. Before founding Wickard.ai, Oliver practiced at Skadden Arps and Jones Day and previously founded a technology startup focused on employment solutions. His legal achievements include successfully arguing twice before the Third Circuit Court of Appeals and securing a cert denial at the U.S. Supreme Court, preserving one of his appellate victories. Oliver is admitted to practice law in New York, Texas, and Washington D.C.