Raymond P. Tolentino

Raymond “Ray” Tolentino is a partner at Kaplan Hecker & Fink LLP.

Ray 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 has litigated a wide array of commercial, constitutional, 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 and has experience in representing clients in congressional investigations. Ray recently 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’s current and recent representations include:

• The Governors of Wisconsin and Pennsylvania in defending their states’ congressional districting maps against challenges at the U.S. Supreme Court 
• 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.
• The City of Philadelphia in Fulton v. Philadelphia—a U.S. Supreme Court merits case involving a First Amendment challenge to the City’s contractual non-discrimination requirements for foster care providers.
• E. Jean Carroll in a case against Donald J. Trump for defamatory statements Trump made in response to Ms. Carroll’s revelation that he had sexually assaulted her.
• Victims of consumer fraud in a federal class action lawsuit against Donald J. Trump, his adult children, and the Trump Organization.
• 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 and mediation proceedings before the U.S. Court of Appeals for the Ninth Circuit.
• A prisoner in a civil rights appeal before the U.S. Court of Appeals for the Second Circuit.

Ray has also filed amicus briefs on behalf of a diverse range of clients, including: 

• 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.
• Scholars of public accommodations law in a Supreme Court case concerning a First Amendment challenge to the application of state anti-discrimination law. 
• A coalition of LGBTQ Rights Organizations as amici curiae in arguing that classifications based on transgender status should be subject to strict scrutiny in the Iowa Supreme Court
• Retired federal judges as amici curiae in support of noncitizen detainees challenging the legality of the federal government’s denial of bond hearings to noncitizens subject to prolonged imprisonment in the Supreme Court.
• Constitutional law scholars as amici curiae in support of a challenge to the State of Mississippi’s law banning the right to an abortion after 15 weeks of pregnancy.
• 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.
• 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.

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 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 where he worked closely with a former U.S. Solicitor General and former Assistant Attorney General.

In addition to his litigation experience, Ray co-authored a 2021 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 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 has previously served as an Adjunct Professor of Law at Georgetown University Law Center, where he taught an Advanced Legal Writing seminar and co-taught “Constitutional Litigation and the Executive Branch.” He is currently 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, was recently recognized by The Legal 500 US for his skill as an appellate litigator, and was selected by Lawdragon 500 as a 2021 and 2022 Leading Plaintiff Employment & Civil Rights Lawyer.

Ray 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, 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. Ray received his B.A., summa cum laude, from Georgetown, where he was elected into Phi Beta Kappa.