Crowley was named the 2011-2012 recipient of the General Omar N. Bradley Chair in Strategic Leadership,[2] a joint initiative among the United States Army War College, Dickinson College and the Pennsylvania State University – Dickinson School of Law.

He spent 26 years in the Air Force, and was stationed in New Hampshire, New York, Massachusetts, Colorado, Washington, Turkey, and Germany.

During the Kosovo War, he worked with Javier Solana, Secretary General of NATO from April to June 1999.

In 2009, President Barack Obama nominated Crowley to be Assistant Secretary of State for Public Affairs.

[6] On March 10, 2011, Crowley publicly criticized the Pentagon for the alleged mistreatment of military prisoner Chelsea (then known as Bradley) Manning, the U.S. soldier suspected of providing whistle-blower website WikiLeaks with classified diplomatic cables.

[7] Crowley told an audience of about twenty people at Massachusetts Institute of Technology's Center for Future Civic Media that while Manning was "in the right place," she was being mistreated by the United States Department of Defense.