Which OpenAI Model for Legal Work? Update for GPT-5

by Avi Gesser, Diane Bernabei, and William J. Sadd

photos of authors

From left to right: Avi Gesser, Diane Bernabei, and William J. Sadd (photos courtesy of Debevoise & Plimpton LLP)

We recently provided a quick guide on the comparative capabilities of the various models currently available through GPT Enterprise based on our experience as lawyers using these models and OpenAI’s own recommendations. Below is an update to that guide based on our use of the new GPT-5 models since they became available to us on August 7, 2025. Again, this blog post is not a review or endorsement of any particular GenAI model.

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AI Use Cases for Lawyers, Part 2—From Audio of a Hearing to Transcript, Summary, PowerPoint and Podcast in Nine Minutes

by Avi Gesser and Michael Pizzi

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From left to right: Avi Gesser and Michael Pizzi (photos courtesy of Debevoise & Plimpton LLP)

In Part 1 of this series, we “vibe coded” a game designed to help train lawyers and professional staff on the firm’s new AI policy using Generative AI. In Part 2, we demonstrate how lawyers can use AI tools to rapidly transcribe and summarize audio recordings from congressional hearings, oral arguments, or depositions, and transform them into a variety of easy-to-digest formats. Specifically, we used NotebookLM and Gamma to transcribe a recent 30-minute Second Circuit oral argument and then create a two-page written summary, a “podcast”-style audio summary, and a PowerPoint presentation—all in under nine minutes.

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Beware the Tariff DDP Trap: Managing Hidden Import Liabilities Before They Bite

by Jonny Frank and Jerry McAdams 

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Left to right: Jonny Frank and Jerry McAdams  (photos courtesy of StoneTurn Group, LLP)

Looking to mitigate tariffs, companies are purchasing foreign products through Duty Paid (“DDP”) transactions marketed by foreign suppliers as turnkey solutions.  DDPs promise efficiency but often deliver exposure. Under U.S. law, the importer—not the supplier—remains legally responsible for accurate customs declarations, tariff payments, and regulatory compliance. When suppliers cut corners or game the system, the importer inherits the fallout, including potential Customs Border Protection (“CBP”) penalties, DOJ criminal prosecution and False Claim Act (“FCA”) exposure.

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SEC’s Newest Task Force Takes Cross-Border Aim

by Jina L. Choi, Gabriela Li, David Woodcock, and Emily Rumble

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From left to right: Jina L. Choi, Gabriela Li, David Woodcock, and Emily Rumble (photos courtesy of Gibson, Dunn & Crutcher LLP)

In line with the Trump Administration’s America First Investment Policy and perhaps in response to entreaties from Congress and state regulators to protect the U.S. capital markets from unscrupulous foreign actors, the SEC announced the formation of a Cross-Border Task Force within its Division of Enforcement on September 5, 2025.[1] The task force will focus on investigating foreign-based issuers for potential market manipulation, such as pump-and-dump and ramp-and-dump schemes, and will increase scrutiny of gatekeepers, particularly auditors and underwriters, who help foreign issuers access the U.S. capital markets. The statement notably singles out China as a jurisdiction where governmental control and other factors pose unique investor risks.

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Future-Proofing Private Equity and Venture Capital: Leveraging AI for Strategic Advantage and Higher Returns

by Sabrina Hannam, Ibe Imo, Shana Sharan, and Ash Buonasera

Left to right: Sabrina Hannam, Ibe Imo, Shana Sharan and Ash Buonasera (photos courtesy of Boardswell)

In the high-stakes world of private equity, venture capital, and technology, a silent revolution is underway, transforming the very essence of how firms operate and compete. It’s a story not of human titans clashing in boardrooms, but of a new collaborator—Artificial Intelligence (AI)—that is rewriting the rules of engagement for human capital management. Once a tool for streamlining simple tasks, AI has evolved into a “digital colleague,” capable of autonomous decision-making and strategic support that extends far beyond the traditional confines of talent acquisition. This shift is challenging long-held practices and heralding an era where success is no longer solely defined by human intuition but by a symbiotic relationship between bold leadership and intelligent machines. Continue reading →

California Adopts New Employment Al Regulations Effective October 1, 2025

by Arsen Kourinian, Ruth Zadikany, and Remy N. Merritt

Left to right: Arsen Kourinian, Ruth Zadikany, and Remy N. Merritt (photos courtesy of Mayer Brown)

The California Civil Rights Council (CRC) recently announced that it has finalized regulations that clarify how California’s anti-discrimination laws apply to the use of artificial intelligence (Al) and automated decision systems (ADSs) in employment decision-making (the “Regulations”). The Regulations provide that the use of an ADS (including Al) in making employment decisions can violate California law if such tools discriminate against employees or applicants — either directly or due to disparate impact — on the basis of protected characteristics (including race, age, religious creed, national origin, gender, and disability).

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Recent Developments in the Law of Federal Property Fraud: It’s a Long and Winding Road

by James Joseph Benjamin Jr., Katherine R. Goldstein, Michael A. Asaro, and Parvin Daphne Moyne 

Left to right: James Joseph Benjamin Jr., Katherine R. Goldstein, Michael A. Asaro, and Parvin Daphne Moyne (photos courtesy of Akin Gump Strauss Hauer & Feld LLP)

In two recent high-profile decisions, Chastain v. United States and Johnson v. United States, the U.S. Court of Appeals for the Second Circuit reversed wire fraud convictions that were based on theories resembling insider trading.[1] In both cases, the government invoked the wire fraud statute, and not a securities fraud statute, because the products at issue (non-fungible tokens and spot foreign currency) were not securities. These cases mark the latest developments in a long-running, ongoing and sometimes head-spinning debate in the courts concerning the breadth of the federal property fraud statutes.

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DOJ Defines “Illegal DEI,” Warns Recipients of Federal Funds to Take Notice

by Adam S. Hickey, Marcia E. Goodman, Ruth Zadikany, and Hiral D. Mehta

Left to right: Adam S. Hickey, Marcia E. Goodman, Ruth Zadikany, and Hiral D. Mehta (photos courtesy of Mayer Brown)

On July 29, 2025, U.S. Attorney General Pam Bondi issued Guidance for Recipients of Federal Funding Regarding Unlawful Discrimination (the “Guidance”). Following the creation of the Civil Rights Fraud  Initiative by the Department of Justice (“DOJ”), and joint guidance issued by DOJ and the U.S. Equal Employment Opportunity Commission (“EEOC”) on “unlawful DEI-related discrimination“, the Guidance is the most tangible guidance released to date on what the administration views as “illegal DEI” and a likely roadmap for DOJ’s False Claims Act (“FCA”) investigations under the Civil Rights Fraud Initiative.

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DOJ Announces First FCPA Enforcement Activity After Months-Long Pause

by Kimberly A. Parker, Jay Holtmeier, Erin G.H. Sloane, and Christopher Cestaro

Left to Right: Kimberly A. Parker, Jay Holtmeier, Erin G.H. Sloane, and Christopher Cestaro (photos courtesy of WilmerHale)

Over the past week, the U.S. Department of Justice (“DOJ”) unsealed its first Foreign Corrupt Practices Act (“FCPA”) enforcement action and issued its first declination since the pause in FCPA enforcement mandated by President Donald Trump’s February 10, 2025 Executive Order (“February Executive Order”)[1] and the subsequent issuance of updated FCPA enforcement guidelines, the Guidelines for Investigations and Enforcement of the Foreign Corrupt Practices Act (FCPA) (“June Guidelines”).[2]  

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Third Circuit Has Opportunity to Rule on Constitutionality of False Claims Act (FCA)

by Joshua Drew, Ian Herbert, Bradley Markano, and Connor Farrell

Left to right: Joshua Drew, Ian Herbert, Bradley Markano, and Connor Farrell (photos courtesy of Miller & Chevalier)

On July 14, 2025, Janssen filed an appeal to the Third Circuit challenging what it characterized in its brief as the “largest ever” judgment under the federal False Claims Act (FCA): approximately $1.6 billion, including over $1.2 billion in civil penalties and $360 million in treble damages. The scope of liability imposed on the healthcare company, along with unique facts underlying the case, present several important constitutional issues, including Article II-based challenges that the FCA’s qui tam provisions improperly delegate to relators the executive authority to pursue punitive quasi-criminal penalties, as well as whether the penalties imposed violate the Fifth Amendment’s Due Process Clause or Eighth Amendment’s Excessive Fines Clause.

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