It’s spring break at the Naval Academy, so where might you find the Commandant of the Midshipmen? Jumping out of an airplane at the Zephyrhills drop zone training camp outside of Tampa, FL, of course. Despite there being roughly 30 years since his last jump and his most recent stint with the team, Captain Robert B. Chadwick II believes in bold leadership. And part of his bold leadership philosophy includes a team-focused mentality where he leads by example. So, skydiving with the US Naval Academy jump team is perfectly aligned with this perspective.
I have been lucky enough to know Captain Chadwick and witness his leadership directly since we were both Midshipmen at the Naval Academy. His brother John and I were classmates, friends, and served on the Honor Committee together. In this video we filmed at the Zephyrhills drop zone, Captain Chadwick provides his perspectives on what it means to be a Bold Leader.
Captain Chadwick’s bold leadership approach involves much more than simply being a role model for others. In his nearly three decades in the US Navy, he has led many to become strong and effective leaders. Whether serving as a fellow naval officer or as a commander, Captain Chadwick has always taken leadership seriously. This fact explains why he continues to receive the US Navy’s highest degree of respect in both leadership awards and positions including a recent selection to Rear Admiral (lower half). It’s also why his bold leadership deserves a more in-depth look.
Growing from Leadership Opportunities—From Student to Naval Academy Commandant
Captain Chadwick currently resides at the Naval Academy Commandant’s house in Annapolis, MD. But it isn’t the first time he has lived here. While Captain Chadwick is the 87th US Naval Academy Commandant, his father was the 71st. As it turns out, Captain Chadwick first lived in the house during his junior year in high school. So, both his father and his early life experiences at the Naval Academy likely helped mold his bold leadership perspectives. This is a first in Naval Academy history, to have both a father and son become the Commandant. Captain Chadwick now joking tells us that he and his father call themselves 87 and 71 in conversations.
Of course, these were not his only leadership influences. After graduation, he was assigned roles as gunnery officer, weapons officer and combat systems officer before becoming executive officer of the USS Philippine Sea. Captain Chadwick received his first commander’s role in 2009 of the USS Roosevelt. In addition, he became the commander of Destroyer Squadron 21 from September 2016 to March 2015. In 2017, he was advanced to the Naval Academy Commandant’s position, where he continues to serve as a bold leader today.

A Bold Leadership Philosophy Deserving of Recognition
When considering his bold leadership philosophy, Captain Chadwick honors three pillars in leading the Midshipmen. These pillars are leadership, character, and accountability. To spur growth in these areas, Captain Chadwick encourages others to seize every opportunity to develop their leadership. As Naval Academy Commandant, he likens experiences to arrow quivers in a bow sack. Good or bad, each experience represents a quiver that can provide leadership development. Experiences under bad leadership can thus offer as many insights as good leadership.
Continued growth and learning are activities that Captain Chadwick consider as essential to bold leadership development. Furthermore, this growth pertains not only to leading others and accepting accountability but also in persistent character development as well.
Captain Chadwick does more than merely preach these bold leadership principles. He also lives by them. This fact is why he was awarded the Vice Admiral James Bond Stockdale Award for Inspirational Leadership in 2011. The award, named for Vice Admiral Stockdale after he received a Medal of Honor for the leadership and valor he embodied during the Vietnam War, honors five key leadership traits. These include serving a leader’s role as a moralist, jurist, teacher, steward, and philosopher. Peers nominate leaders for this award. And only two naval officers can receive this recognition each year. Captain Chadwick was one of them.

Humility as a Bold Leadership Trait
For the US Naval Academy commandant, humility is an essential aspect of bold leadership. Captain Chadwick values humility as a way to allow others to develop their own leadership skills. His most profound experience was when he was asked to oversee a naval vessel that had failed inspection. By being humble, rather than authoritative, he fostered a team mentality with his crew. At the same time, by being bold, he was able to boost morale and initiative. As a result, the entire crew excelled overcoming multiple adversities along the way.
Captain Chadwick’s philosophy of humility permeates each leadership role that he has pursued and held. For example, when receiving the Stockdale Award, he attributed his success to his crew and asked them to sign the back of the award. This action reflected his overall recognition that any success he has had as a leader involved others and his team. It’s also the reason he chose to jump 13,000 feet with the jump team as their Naval Academy Commandant. He never puts any task above himself and values the men and women he leads as co-equals. He believes in each one of them, encourages and instills trust in them that they will accomplish the task or mission.
Through his actions, Captain Chadwick serves as a role model for others—showing in tangible ways how leaders can be both humble and bold. In this way, he continues to foster leadership development among those under his command.

At the Heart of It All Stands Character
As one of Captain Chadwick’s bold leadership pillars, character represents a crucial component. Such character highlights honesty, respect, and trust when interacting with others. And it means serving with integrity and authenticity. For Captain Chadwick, that is essential when it comes to bold leadership.
Throughout the 173-year history of the Navy, a father and son have never both served as Naval Academy Commandant—until now. His bold leadership philosophy and approach has made a tremendous impact on others around him throughout his career. And this case is not about to change as he embarks on future leadership positions.

Whether jumping from planes or attending midshipmen graduations, Captain Robert B. Chadwick II continues to embrace every leadership opportunity he can. Clearly, his influence will be felt for many generations to come.
To learn more about Captain Chadwick, read our accompanying article on how the US Naval Academy and how the institution is changing with evolving times.
For the full-length interview. watch it here.