Ten years ago, a new tradition was born when Miss Porter’s School began inviting Ancients to serve as graduation speakers. This year, we are pleased to announce Jaime Cheshire ’95 as the commencement speaker for the Class of 2024.
Jaime Cheshire is a senior national security professional with 25 years of service on Capitol Hill and in the Intelligence Community.
She currently serves as executive director of the Afghanistan War Commission, an independent, bipartisan legislative commission established by the U.S. Congress to conduct a comprehensive review of key decisions related to U.S. military, intelligence, foreign assistance, and diplomatic involvement in Afghanistan from June 2001 to August 2021.
Previously, Jaime served as a senior intelligence service officer in the Intelligence Community. As executive secretary (ExecSec) of an agency, she oversaw both the Action Center and the Operations Center, providing 24-7 support to agency leadership and the White House.
Prior to ExecSec, Jaime served as director of the Office of Congressional Affairs, where she advised the agency’s senior leadership on all legislative strategy and oversight matters and served as the agency’s primary liaison to the U.S. Congress. For her agency service, she received the President Rank Award and the Director’s Award three times.
From 2009-2017, Jaime served as a professional staffer and senior advisor to the chairman of the House Armed Services Committee. She helped enact seven consecutive National Defense Authorization Acts while navigating committee and floor debates on critical national security issues. In this role, she conducted six oversight trips into Afghanistan.
Earlier in her career, Jaime served as legislative director to Rep. Buck McKeon (CA) and her home district representative, Rep. Nancy Johnson (CT), a senior member of the Ways and Means Committee.
A native of Farmington, Connecticut, Jaime holds a Bachelor of Arts in political science from the University of Connecticut and served as a member of the College of Liberal Arts and Sciences Dean’s Advisory Board. She currently serves as a member of the Political Science Department Advisory Board.
Jaime completed her lifelong goal of a 2,200 mile thru-hike of the Appalachian Trail in 2021.
