About Raymond

Ray is an experienced litigator, strategic counselor and former senior US government lawyer who focuses on complex commercial litigation, appellate litigation and crisis management. He has extensive experience guiding clients through cutting-edge business disputes, government-facing litigation, high-stakes regulatory proceedings and sensitive investigations in matters involving administrative, constitutional, education, labor and employment, healthcare, financial regulation and civil rights law. Drawing on his experience working in every branch of the US federal government, including serving as a law clerk on the US Supreme Court, Ray assists clients in navigating shifting regulatory environments and advises companies, nonprofits, universities and executives on how to mitigate and address legal, regulatory and reputational risk. He also maintains a robust public interest and pro bono practice focused on antidiscrimination law, immigrants’ rights, gun violence prevention, criminal justice, voting rights, and LGBTQ+ and gender equality. For example, Ray served as trial counsel and lead appellate counsel for plaintiffs in securing a landmark multimillion-dollar verdict against the neo-Nazis and white supremacists who organized the racially motivated violence in Charlottesville, Virginia, in the summer of 2017.

View full bio

Admissions and credentials

  • New York
  • District of Columbia

Experience

  • Cooley Wins Major Fourth Circuit Victory for Pro Bono Client Trokon Diahn

    • Cooley Wins Major Fourth Circuit Victory for Pro Bono Client Trokon Diahn

    May 7, 2026

    Cooley won a major victory on behalf of its pro bono client Trokon Diahn after the US Court of Appeals for the Fourth Circuit granted his petition for review, vacated his removal order and remanded his case for further proceedings. In its published decision on May 5, 2026, the court addressed administrative exhaustion and the scope of immigration judges’ obligations in cases involving pro se respondents. The Cooley team representing Diahn on appeal included partner Raymond P. Tolentino and associate Sahar Atassi, who presented oral argument on behalf of Diahn in the Fourth Circuit.

    Read more

    Related contacts

    Raymond P. Tolentino
    Partner, Washington, DC
    Sahar Atassi
    Associate, Washington, DC

    Related Practices & Industries

    Supreme Court and Appellate
    Trials
    Pro Bono

  • Cooley Argues for Transgender Student Athletes Before US Supreme Court

    • Cooley Argues for Transgender Student Athletes Before US Supreme Court

    January 13, 2026

    Cooley appeared before the Supreme Court of the United States as it heard oral arguments in West Virginia v. BPJ and Little v. Hecox, two cases challenging laws that categorically bar transgender girls and women from participating on girls’ and women’s school sports teams. Cooley partner Kathleen Hartnett presented argument for Lindsay Hecox, a transgender woman who challenged an Idaho law barring all transgender girls and women from participating on girls’ and women’s school sports teams. Hartnett led the Cooley team, which includes partners Raymond Tolentino and Ephraim McDowell, special counsel Joshua Revesz and Patrick Hayden, and associates Katelyn Kang, Elias Kim, Valeria Pelet del Toro, Elizabeth Reinhardt, Zoë Helstrom and Celene Chen.

    Read more

    Related contacts

    Kathleen R. Hartnett
    Partner, San Francisco
    Raymond P. Tolentino
    Partner, Washington, DC
    Ephraim McDowell
    Partner, Washington, DC
    Joshua Revesz
    Special Counsel, Washington, DC
    Patrick J. Hayden
    Special Counsel, New York
    Katelyn Kang
    Associate, New York
    Elias S. Kim
    Associate, Washington, DC
    Valeria M. Pelet del Toro
    Associate, New York
    Elizabeth Reinhardt
    Associate, Washington, DC
    Zoë Helstrom
    Associate, San Francisco
    Celene Chen
    Associate, Boston

    Related Practices & Industries

    Pro Bono
    Supreme Court and Appellate
    Trials
    Commercial Litigation

Rankings and accolades

Benchmark Litigation: 40 & Under List (2022 – 2023)

National Law Journal: DC Rising Star (2023)

Lawdragon: 500 Leading Litigators in America (2024)

Best Lawyers: Ones to Watch – Appellate Practice (2023 – 2024)

Lawdragon: 500 X – The Next Generation (2023 – 2024)

Government Service

Special Assistant to the President and Senior Associate Counsel, Office of the White House Counsel

Special Counsel to Sen. Amy Klobuchar, Senate Judiciary Committee

Clerkships

Justice Sonia Sotomayor, US Supreme Court

Judge Cornelia T.L. Pillard, US Court of Appeals for the DC Circuit

Judge M. Margaret McKeown, US Court of Appeals for the Ninth Circuit

Judge Kiyo A. Matsumoto, US District Court for the Eastern District of New York

Memberships and affiliations

  • American Law Institute, elected member
  • Edward Coke Appellate Inn of Court, barrister
  • Leadership Counsel on Legal Diversity, fellow
  • Honorable Order of Kentucky Colonels, member
  • Asian Pacific American Bar Association of the Greater Washington, DC, Area, member
  • The Appellate Project, mentor

This content is provided for general informational purposes only, and your access or use of the content does not create an attorney-client relationship between you or your organization and Cooley LLP, Cooley (UK) LLP, or any other affiliated practice or entity (collectively referred to as "Cooley"). By accessing this content, you agree that the information provided does not constitute legal or other professional advice. This content is not a substitute for obtaining legal advice from a qualified attorney licensed in your jurisdiction, and you should not act or refrain from acting based on this content. This content may be changed without notice. It is not guaranteed to be complete, correct or up to date, and it may not reflect the most current legal developments. Prior results do not guarantee a similar outcome. Do not send any confidential information to Cooley, as we do not have any duty to keep any information you provide to us confidential. When advising companies, our attorney-client relationship is with the company, not with any individual. This content may have been generated with the assistance of artificial intelligence (Al) in accordance with our Al Principles, may be considered Attorney Advertising and is subject to our legal notices.