William J. Gallagher, headmaster of Holy Cross School, N.O.

William J. Gallagher, a graduate and former trustee of the U.S. Military Academy at West Point, was named the 18th headmaster of Holy Cross School in March following a nationwide search by the school’s board of directors.

Gallagher, who began his appointment on March 28, brings an impressive portfolio with experience in military, education and humanitarian leadership both nationally and globally. 

A combat veteran with three tours of duty, he was the chief of plans for the U.S. Army during the Iraq war, where he led a team of 17 senior military officers in developing the strategy for this rapidly deployed and dynamic engagement. Gallagher was also Basic Training Battalion Commander for more than 1,000 soldiers at Fort Jackson, South Carolina.

He commanded infantry units from platoon through brigade during his 28-year U.S. Army career and served as special assistant to the U.S. Army Chief of Staff at the Pentagon. 

Upon his retirement as a colonel in the U.S. Army, Gallagher turned his energy and passion to education and the global humanitarian peace process. He led the startup of New York University’s major expansion into the United Arab Emirates and served as associate vice chancellor of operations and administration. He then served on the faculty of West Point as well as the Harvard Kennedy School of Government in Cambridge, Massachusetts.

In addition to serving as president of Riverside Military Academy in Georgia, he also served as dean of the college at Valley Forge Military Academy & College in Pennsylvania, where he proved to be a masterful entrepreneurial leader, educational visionary and prolific fundraiser. 

Gallagher most recently was chief of staff and strategic advisor representing the U.S. State Department in its humanitarian and peacekeeping efforts in South Sudan.

A lifelong, practicing Catholic, Gallagher attended St. Joseph’s Preparatory School in Philadelphia, a highly respected all-boys’ Catholic school. He received his bachelor’s degree in aeronautical engineering from the U.S. Military Academy at West Point, New York. He also earned a master’s degree in leadership development from West Point and would later earn a master of business administration from Long Island University.

In his first full academic year at Holy Cross, Gallagher said he hopes to nurture the ideal incorporated in the Holy Cross creed that a graduate become a “refined gentleman.”

“It’s a very exciting time for the school, it’s a transformative period for the school,” Gallagher said. “We are in some ways going back to the traditions a little more in terms of dress code, appearance and discipline. Yet, at the same time, we're looking forward more aggressively at what new programs we can add to attract young people and young parents – such as cybersecurity, an enhanced robotics program, a class called ‘Essential Skills for the Holy Cross Man,’ which is really life skills.”

One of the curriculum changes will be a schedule exclusively comprising academic classes.

“My charge is to make sure that in all that time being spent (in class), we’re getting the absolute most juice from that squeeze in the classroom,” Gallagher said. 

Gallagher and his administrative team have spent the summer drafting a five-year strategic plan and a master campus plan. Those plans, which will be presented to the board of directors, will emphasize information technology and also outline how to finance those improvements. 

Gallagher said the emphasis with students regarding structure and discipline will produce amazing outcomes.

“When you have a system of rules that govern behavior, appearance, decorum and courtesy, it gives a teenager dozens of opportunities a day to choose either the harder right or the easier wrong,” Gallagher said. “Building one’s character and integrity is much like building your bicep. You test your character with a choice. One is a tempting, fun, exciting option, and the other is the right thing to do. When you fend off the temptation and choose the harder right, you’re building your character, just a little bit, by that decision.”