Raymond P. Tolentino

Raymond (“Ray”) P. Tolentino serves as an attorney in the Executive Branch, where he provides legal counsel to government officials and agencies. Before entering government service, Ray was a partner at Kaplan Hecker & Fink LLP, where he specialized in appellate and complex civil litigation and represented clients in a wide array of commercial, constitutional, and civil rights cases. He also previously served as the faculty director of the Howard University School of Law Civil Rights Clinic, where he supervised clinical students in litigating high-stakes civil rights appeals before the Supreme Court and federal appellate courts, and held an appointment as an Adjunct Professor of Law at Georgetown University Law Center, where he co-teaches an advanced seminar on Constitutional Law.

Tolentino has served as the principal author of dozens of briefs filed in the U.S. Supreme Court, federal courts of appeals, and federal and state trial courts and regularly advises individuals and companies in high-stakes trial litigation, regulatory matters, and congressional investigations.

In 2021, Tolentino served among trial counsel for several 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. In October 2020, he took a leave of absence from Kaplan Hecker to serve as Special Counsel to Senator Amy Klobuchar on the Senate Judiciary Committee for the Supreme Court confirmation hearing of Justice Amy Coney Barrett.

Before joining Kaplan Hecker, Tolentino was counsel at Akin Gump Strauss Hauer & Feld LLP, where he was a member of the Supreme Court and Appellate group. He previously served as a law clerk for Justice Sonia Sotomayor of the Supreme Court of the United States, Judge Cornelia T.L. Pillard of the U.S. Court of Appeals for the D.C. Circuit, Judge M. Margaret McKeown of the United States Court of Appeals for the Ninth Circuit, and Judge Kiyo A. Matsumoto of the United States District Court for the Eastern District of New York.

Tolentino is a barrister in the Edward Coke Appellate Inn of Court and was appointed to the editorial board of the American Bar Assocation's Litigation Journal. He was named a D.C. Rising Star by the National Law Journal and has appeared on Benchmark’s “40 & Under Hot List,” Best Lawyers “Ones to Watch, Appellate Practice,” and Lawdragon 500’s List of Leading Plaintiff Employment and Civil Rights Lawyers. Tolentino is a member of The Appellate Project, APABA-DC, and the Leadership Council on Legal Diversity.

Tolentino received his J.D., summa cum laude, from the Georgetown University Law Center, where he received the Francis E. Lucey, S.J. Award for graduating first in his class and served as the Senior Articles Editor of The Georgetown Law Journal. Tolentino received his B.A., summa cum laude, from Georgetown, where he was elected into Phi Beta Kappa.