Karen Chesley

Karen is an experienced commercial litigator who serves as Assistant General Counsel at The New York Times. She manages The Times’s litigation against Microsoft, OpenAI, and Perplexity for copying millions of Times articles to build and operate generative AI products that compete with The Times’s journalism.

Prior to joining The Times, Karen was a partner at Boies Schiller Flexner, where she focused on high-stakes litigation, including contract disputes, trade secrets litigation, copyright matters, shareholder lawsuits, and cases involving international law. She is also an experienced appellate litigator, having worked on appeals before the Courts of Appeals for the Second, Third, Fifth, Tenth, and D.C. Circuits, and served as lead appellate counsel in a New York First Department appeal that led to the reversal of a substantial defamation judgment. In 2019, she was named a New York Law Journal Rising Star.

Karen served as a law clerk in the U.S. Court of Appeals for the Third Circuit and the U.S. District Court for the Eastern District of Pennsylvania. She holds a bachelor’s degree, summa cum laude, from Syracuse University and a J.D., cum laude, from the University of Pennsylvania Carey Law School, where she was a member of the Law Review and President of the Penn Intellectual Property Group.