About Raymond Patrick
Raymond Patrick Tolentino has built a career that moves between courts, classrooms and Capitol Hill. He studied English and Japanese as an undergraduate at Georgetown University, graduating in 2009, and returned to earn his law degree from Georgetown University Law Center in 2012. Those years left him with a grounding in written argument and an interest in appellate work.
His first years after law school were marked by a series of federal clerkships. He served on the U.S. District Court for the Eastern District of New York for Judge Kiyo A. Matsumoto in 2012. The next year took him to the Ninth Circuit, where he clerked for Judge M. Margaret McKeown. He spent 2015 clerking for Judge Nina Pillard on the D.C. Circuit, then in 2017 he clerked for Justice Sonia Sotomayor at the Supreme Court of the United States. Those posts exposed him to a wide range of federal issues and appellate procedure.
Between and after those clerkships he worked in private practice. In 2014 he was an associate at Bancroft PLLC. He later joined Akin Gump Strauss Hauer & Feld LLP as an associate in 2016 and returned there as counsel in 2018. In 2016 he also taught as an adjunct professor of law at Georgetown University Law Center, bringing courtroom experience into the classroom.
Tolentino’s résumé includes a brief stint in public service at the Senate Judiciary Committee in 2020, where he served as special counsel to Senator Amy Klobuchar. That role placed him in the middle of legislative and oversight work and added a policy dimension to his litigation background. Later in 2020 he moved to Kaplan Hecker & Fink LLP as counsel, continuing a mix of appellate and trial-related work.
Outside of jobs and clerkships, he participates in professional groups that align with appellate practice and bar leadership. He is a member of the Edward Coke Appellate Inn of Court and belongs to the District of Columbia Bar and the New York State Bar, the latter since 2013. He is also a Fellow of the Leadership Council on Legal Diversity and holds an honorary Kentucky Colonel designation.
Observers of his career note a throughline: frequent work in appellate courts, repeated exposure to federal constitutional and statutory questions, and engagement with legal education. He currently practices at Kaplan Hecker & Fink LLP, where his work centers on appellate litigation and federal proceedings.
