Raymond P. Tolentino

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.

Before joining Cooley, Ray served as special assistant to the president and senior associate counsel in the Office of the White House Counsel, providing legal and strategic advice to the president, vice president, senior White House officials and federal agencies on civil rights, constitutional, regulatory and administrative law issues. At the White House, Ray helped oversee high-profile litigation involving the federal government and worked with executive branch officials to shape and implement regulations and policies related to artificial intelligence, antidiscrimination law, labor and employment policy, education, reproductive rights, environmental protection, disability rights, criminal justice reform and voting rights. Before serving as a White House official, Ray was a partner at a litigation boutique, where he litigated groundbreaking commercial, civil rights and criminal cases and served as the firm’s deputy general counsel. In October 2020, Ray served as special counsel to US Sen. Amy Klobuchar on the Senate Judiciary Committee for the Supreme Court confirmation hearing of Justice Amy Coney Barrett.  

Ray currently serves as an adjunct professor of law at Georgetown University Law Center, where he teaches a seminar, Contemporary Civil Rights Issues at the Supreme Court. From 2022 to 2024, Ray was an adjunct professor at Howard University Law School, where he served as the faculty director of the Civil Rights Clinic. Ray’s white papers, articles and op-eds have appeared in Time magazine, NBC News and Brookings Institution publications, and he regularly speaks to law students, lawyers, bar associations and law professors on various topics, including civil rights law, constitutional law and public interest litigation.

Ray clerked for Supreme Court Justice Sonia Sotomayor, Judge Cornelia T.L. Pillard of the US Court of Appeals for the District of Columbia Circuit, Judge M. Margaret McKeown of the US Court of Appeals for the Ninth Circuit and Judge Kiyo A. Matsumoto of the US District Court for the Eastern District of New York. He graduated first in his class from Georgetown University Law Center.

Ray’s representative matters:

Complex commercial litigation and class actions

• Representing major tech companies, startups and founders in cutting-edge litigation
• Representing a large mortgage lender in a putative nationwide consumer class action in federal district court
• Representing a top university and its employees in Title IX litigation
• Representing a climate analytics company in a complex commercial dispute in New York state court
• Represented a university in successfully obtaining dismissal of a putative class action filed by a student alleging statutory and constitutional claims against the university’s law school*

Supreme Court and appellate matters

• Representing transgender athletes in challenging the constitutionality of state laws banning transgender participation in sports at the Supreme Court
• Representing the heirs of a renowned artist in a lawsuit seeking the return of paintings acquired by a German museum at the US Court of Appeals for the DC Circuit
• Serving as appellate counsel for a major online gaming company in a high-profile litigation over the enforceability of the company’s arbitration agreements
• Represented the governors of Wisconsin and Pennsylvania in defending their states’ congressional redistricting maps against challenges at the Supreme Court*
• Represented the Commonwealth of Pennsylvania in successfully defending its certification of the results of the 2020 presidential election at the Supreme Court*
• Represented Kentucky Gov. Andy Beshear in successfully defending the constitutionality of his COVID-19 public health orders at the Supreme Court*
• Represented civil rights litigants in police misconduct cases at the Supreme Court*

Regulatory litigation, investigations and government-facing disputes

• Advising a major university in federal investigations and inquiries
• Representing a life sciences company in a potential Administrative Procedure Act and constitutional challenge to a recently promulgated agency rule
• Advising major tech companies on potential legal and administrative challenges to state and federal laws and regulations
• Representing a space technology company in an administrative challenge to an adverse agency ruling
• Defended a state transit authority in multiple lawsuits raising statutory, environmental and constitutional challenges to a novel transportation initiative*
• Represented a financial services company in proceedings before the US Consumer Financial Protection Bureau and related litigation*

Civil rights and public interest litigation

• Representing an Alabama death row inmate in an ongoing legal challenge to his capital conviction
• Representing a civil rights plaintiff in federal litigation alleging constitutional violations against police officers and police departments in Louisiana
• 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*
• Successfully briefed and argued appeals on behalf of civil rights plaintiffs before the US Court of Appeals for the Second Circuit and Fifth Circuit*
• Represented Black women law scholars as amici curiae in defending the constitutionality of race-conscious admissions programs adopted by Harvard University and the University of North Carolina*
• Represented constitutional law scholars as amici curiae in support of a challenge to a Mississippi state law banning the right to an abortion after 15 weeks of pregnancy*

* Representation handled before joining Cooley