CPT Will Oakley

CPT Will Oakley is an instructor in the Department of Social Sciences at the United States Military Academy (USMA). He grew up in Lake Forest, Illinois, as the oldest of three brothers.

A 2016 USMA graduate, he competed on the policy debate team and commissioned with a bachelor's degree in international relations.

CPT Oakley has led infantry and military intelligence teams in light, motorized, airborne, and joint organizations. He deployed in support of Operation Inherent Resolve (2019-20) and the U.S. Special Operations Command mission in Somalia (2022-23).

He holds a master’s degree in public policy from the Harvard Kennedy School. His research focuses on security cooperation, agency theory, crisis bargaining, and violent spillover in civil wars.