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, 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 protection, criminal justice, voting rights, and LGBTQ+ and gender equality.

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, working 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 is also a law professor and legal scholar, currently serving as an adjunct professor of law at Georgetown University Law Center, where he teaches the 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 US 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:

• 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*

• 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*

• 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*

• Represented major tech and fintech companies in cutting-edge litigation, including putative class actions*

• Represented the governors of Wisconsin and Pennsylvania in defending their states’ congressional redistricting maps against challenges at the US Supreme Court*

• Represented the Commonwealth of Pennsylvania in successfully defending its certification of the results of the 2020 presidential election at the US Supreme Court*

• Represented Gov. Andy Beshear of Kentucky in successfully defending the constitutionality of his COVID-19 public health orders at the US Supreme Court*

• Successfully briefed and argued appeals on behalf of civil rights plaintiffs before the US Court of Appeals for the Second Circuit and the 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 a coalition of LGBTQ+ rights organizations as amici curiae in arguing that classifications based on transgender status should be subject to heightened scrutiny in the Iowa Supreme Court*

• Represented retired federal judges as amici curiae in support of noncitizen detainees challenging the legality of the US federal government’s denial of bond hearings to noncitizens subject to prolonged imprisonment in the Supreme Court*

• 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