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- B.A., Georgetown University
- summa cum laude and Phi Beta Kappa
- J.D., Georgetown University Law Center, 2012
- summa cum laude
- Hon. Sonia Sotomayor, U.S. Supreme Court
- Hon. Cornelia T.L. Pillard, U.S. Court of Appeals for the D.C. Circuit
- Hon. M. Margaret McKeown, U.S. Court of Appeals for the Ninth Circuit
- Hon. Kiyo A. Matsumoto, U.S. District Court for the Eastern District of New York
Fellowships, Leadership & Recognition
- Member, Edward Coke Appellate Inn of Court
- Fellow, Leadership Council on Legal Diversity
- Kentucky Colonel, Commonwealth of Kentucky
- Recognized for Appellate Litigation, Legal 500 US, 2019
- Francis E. Lucey, S.J. Award, Georgetown University Law Center
- Senior Articles Editor & Senior Executive Board Member, The Georgetown Law Journal
- Order of the Coif, Georgetown University Law Center
- CALI Awards For Top Exams, Georgetown University Law Center
- Legal Research & Writing Fellow, Georgetown University Law Center
- Senior Writing Fellow, Georgetown University Law Center
- Global Teaching Fellow, Georgetown University Law Center
- Executive Board Member, Asian Pacific American Law Students Association, Georgetown University Law Center
Bar and Court Admissions
- U.S. Courts of Appeals for the District of Columbia, Federal, Second, Third, Fourth, Fifth, Sixth, Seventh, Ninth, and Eleventh Circuits
- U.S. Court of International Trade
- U.S. District Court for the District of Columbia
- U.S. District Court for the Southern District of New York and Eastern District of New York
- U.S. District Court for the Western District of Michigan
- District of Columbia
- New York
Raymond “Ray” Tolentino is counsel at Kaplan Hecker & Fink LLP. He specializes in appellate and complex civil litigation, and has substantial experience representing clients in matters related to administrative, constitutional, employment, healthcare, and civil rights law. 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. In October 2020, Ray took a leave of absence from the firm to serve as Special Counsel to Senator Amy Klobuchar on the Senate Judiciary Committee for the Supreme Court nomination of Justice Amy Coney Barrett.
Ray has litigated a wide array of commercial and civil rights cases and 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.
His current and recent representations include:
- The Commonwealth of Pennsylvania in defending its certification of the results of the 2020 presidential election at the U.S. Supreme Court.
- Governor Andy Beshear of Kentucky in defending the constitutionality of his COVID-19 public health orders at the U.S. Supreme Court.
- Victims of consumer fraud in a federal class action lawsuit against Donald J. Trump, his adult children, and the Trump Organization.
- The City of Seattle as amicus curiae opposing a constitutional challenge under the Takings Clause that would undermine local health and safety regimes at the U.S. Supreme Court.
- Maryland and the District of Columbia—as well as private parties—in challenges to President Trump’s violation of the Emoluments Clauses at the U.S. Supreme Court.
- An LGBTQ asylum seeker from El Salvador in appellate proceedings before the U.S. Court of Appeals for the Ninth Circuit.
- The Movement for Family Power as amicus curiae in support of a longtime U.S. resident’s challenge to a final order of removal in the U.S. Court of Appeals for the Second Circuit.
- Renowned historical scholars as amici curiae in support of a challenge to the federal government’s invocation of the Public Health Service Act as a basis to deport noncitizens at the border in proceedings before the U.S. Court of Appeals for the D.C. Circuit and the U.S. District Court for the District of Columbia.
- Leading epidemiologists as amici curiae in support of Governor Gretchen Whitmer's executive orders designed to combat the spread of COVID-19 in Michigan federal and state courts.
- Constitutional law scholars as amici curiae in support of the City of Los Angeles’s COVID-19 eviction moratorium before the U.S. Court of Appeals for the Ninth Circuit.
Ray is an active member of Kaplan Hecker’s Diversity, Equity, & Inclusion Committee and is 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 also serves as an Adjunct Professor of Law at Georgetown University Law Center, where he teaches an Advanced Legal Writing seminar and co-teaches “Constitutional Litigation and the Executive Branch”.
Ray joined Kaplan Hecker from Akin Gump Strauss Hauer & Feld LLP, where he was a member of the firm’s Supreme Court and Appellate group. During his tenure at Akin Gump, Ray successfully argued an appeal on behalf of a civil rights plaintiff in the U.S. Court of Appeals for the 5th Circuit; cross-examined a police officer and argued a suppression motion on behalf a criminal defendant in Maryland state court; spearheaded pro bono litigation securing asylum for an Ethiopian woman who suffered persecution and torture in her home country; and briefed numerous matters on behalf of individuals, casinos, sports leagues, trade associations, as well as companies in the retail, telecommunications, biotechnology, healthcare, and financial services industries.
Ray has served as a law clerk at every level of the federal judiciary, having clerked for the Hon. Sonia Sotomayor of the Supreme Court of the United States, the Hon. Cornelia T.L. Pillard of the United States Court of Appeals for the D.C. Circuit, the Hon. M. Margaret McKeown of the United States Court of Appeals for the Ninth Circuit, and the Hon. Kiyo A. Matsumoto of the United States District Court for the Eastern District of New York. In between clerkships, Ray also worked as an associate at Bancroft PLLC.
Ray graduated 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, among other academic honors. As a Georgetown Law student, Ray served as an intern at the U.S. Department of Justice (for both the Civil Appellate Division and the Civil Rights Division) and was Senior Articles Editor and a member of the Senior Executive Board and Diversity Review Board of The Georgetown Law Journal. He also built substantial research, clinical, and teaching experience at the Law Center, and maintained an active pro bono practice. Ray received his B.A. in English from Georgetown, where he was elected into Phi Beta Kappa and graduated summa cum laude.