Raymond (“Ray”) Tolentino is a litigator and strategic counselor. He recently served as Special Assistant to the President and Senior Associate Counsel in the Office of the White House Counsel, where he provided legal advice to the President, Vice President, senior government officials, and federal agencies. Before his tenure as a White House lawyer, Professor Tolentino was a partner at Kaplan Hecker & Fink LLP, where he specialized in appellate and complex civil litigation and represented parties in matters related to administrative, constitutional, employment, healthcare, and civil rights law. Professor Tolentino is a barrister in the Edward Coke Appellate Inn of Court, was recently recognized by the Best Lawyers and Legal 500 US for his skill as an appellate litigator, and was selected for inclusion in Lawdragon 500’s 2021 and 2022 list of Leading Plaintiff Employment & Civil Rights Lawyer and in Benchmark Litigation‘s 40 & Under Hot List. From 2022 until 2024, Professor Tolentino served as an Adjunct Professor and Co-Director of the Howard University School of Law Civil Rights Clinic.

In October 2020, Professor Tolentino 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.

Earlier in his career, Professor Tolentino was counsel at Akin Gump Strauss Hauer & Feld LLP, where he was a member of the Supreme Court and Appellate group. He 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.

Professor Tolentino graduated summa cum laude from Georgetown University Law Center in 2012, where he was the recipient of the Francis E. Lucey, S.J. Award, the Senior Articles Editor of The Georgetown Law Journal, a law fellow and a senior writing fellow for the Legal Research and Writing Program, and a member of the moot court team. He received his undergraduate degree in English, summa cum laude, from Georgetown University.