The Henry Crown Leadership Award was created to honor an outstanding leader whose achievements reflect the high standards of honor, integrity, industry, and philanthropy that characterized the life and career of Henry Crown. The award is presented annually by the Trustee of the Henry and Gladys Crown Charitable Trust Fund in cooperation with the Henry Crown Fellowship Program of the Aspen Institute.

In 2015, the Henry Crown Leadership Award was presented to General (ret.) Stanley McChrystal, former Commander of the International Security Assistance Force and Commander of United States Forces Afghanistan. Stanley's career in the U.S. Army spanned 34 years. Prior to his service in Afghanistan, he served as Director of the Joint Staff, where he assisted the Chairman of the Joint Chiefs of Staff in managing the direction, operation, and integration of all combat land, naval, and air forces. He also commanded the Joint Special Operations Command, overseeing elite US military forces in Iraq, Afghanistan, and elsewhere around the world. He is now the Co-Founder of McChrystal Group LLC and is also heading the Aspen Institute Franklin Project to encourage and promote national service. 

Past recipients of the award include:

2014Reed Hastings, Founder and CEO, Netflix
2013Wynton Marsalis, Managing and Artistic Director, Jazz at Lincoln Center
2012Gabrielle Giffords, former U.S. Representative
2011Madeleine K. Albright, Chair, The Albright Stonebridge Group and former United States Secretary of State
2010Vartan Gregorian, President, Carnegie Corporation of New York
2009Jeffrey Bezos, President, CEO, and Chairman of the Board of
2008William Mayer, Partner, Park Avenue Equity Partners and former Chairman of the Aspen Institute Board of Trustees
2007No award was presented in 2007
2006Condoleezza Rice, former United States Secretary of State
2005William Budinger, Founder, Rodel Inc.
2004Michael Powell, former Chairman of the Federal Communications Commission, and member of the TripleCrown Class of Henry Crown Fellows.  Michael was the first Henry Crown Fellow to receive this award
2003Patty Stonesifer, Co-Chair and President of the Bill and Melinda Gates Foundation
2002Jimmy Carter, thirty-ninth president of the United States
2001Dr. William J. Perry, professor at Stanford University, senior fellow at the Hoover Institution, and co-director of the Preventative Defense Project. Among his many accomplishments, Dr. Perry served as the 19th Secretary of Defense for the United States from 1994 to 1997.
2000Sen. George J. Mitchell, former Majority Leader of the United States Senate
1999Gen. Colin L. Powell, USA (Ret.), founding chairman of America's Promise - The Alliance for Youth and former U.S. Secretary of State
1998Norman R. Augustine, former vice chairman and chief executive officer of Lockheed Martin Corporation and Professor at Princeton University
1997Robert W. Galvin, chairman of the executive committee of Motorola, Inc.