In 1987, John Hanly became headmaster. He served until 2000, and was well-liked and remembered by members of the community. Today, the Hanly Lecture on Ethics and Morality holds his name. John Neiswender became headmaster after Hanly, and served until 2005. Nathaniel Conard was headmaster from July 2005 to mid-2019. In late 2018, the shool announced that Matt Levinson, of University Prep in Seattle, would be Head of School after Conard retired in mid-2019. Since Pingry's day, there have been 16 headmasters. Currently, Levinson holds the post, his appointment effective mid-2019.