Raymond “Ray” Tolentino is a partner at Kaplan Hecker & Fink LLP, specializing in appellate and complex civil litigation. Ray represents clients in a wide variety of matters including administrative, constitutional, employment, healthcare, and civil rights law. He 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. Ray also regularly advises companies in high-stakes trial litigation and regulatory matters and has experience in representing clients in congressional investigation.
Ray 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. Ray has an impressive election practice, having represented the Governors of Wisconsin and Pennsylvania in defending their states’ congressional districting maps against challenges at the U.S. Supreme Court and the Commonwealth of Pennsylvania in defending its certification of the results of the 2020 presidential election at the U.S. Supreme Court. During the COVID-19 pandemic, Ray represented Governor Andy Beshear of Kentucky in defending the constitutionality of his COVID-19 public health orders at the U.S. Supreme Court, and recently represented black women law scholars as amici curiae in defending the constitutionality of race-conscious admissions adopted by Harvard University and the University of North Carolina.in the U.S. Supreme Court.
In addition to his litigation experience, in 2020, Ray took a leave of absence to serve as Special Counsel to Senator Amy Klobuchar on the Senate Judiciary Committee for the Supreme Court nomination of Justice Amy Coney Barrett. The following year, he co-authored a Brookings Institute Report entitled Fulton County, Georgia’s Trump Investigation: An Analysis of the Reported Facts and Applicable Law, alongside former Ambassador Norman Eisen, Joshua Matz, Donald Ayer, Gwen Keyes Fleming, Jason Harrow, and Colby Galliher. Ray is also an active member of Kaplan Hecker’s Diversity, Equity, & Inclusion Committee and was the firm’s 2021 Fellow to the Leadership Council on Legal Diversity. He serves as a mentor to law students for The Appellate Project, APABA-DC, and the Justice Initiative.
Ray graduated summa cum laude from the Georgetown University Law Center. Currently, he is an Adjunct Professor at Howard University Law School, where he serves as the Co-Director of the Law School’s Civil Rights Clinic. Ray is a member of the Edward Coke Appellate Inn of Court and was recently recognized by the Legal 500 US for his skill as an appellate litigator. Ray was selected as Best Lawyers’ Ones to Watch, Appellate Practice in 2023, Lawdragon 500’s Leading Plaintiff Employment & Civil Rights Lawyer, and Benchmark Litigation’s 40 & Under List in 2022.
Updated July 2023
