The Vanguard — Diego Henao Ospina ’28

The Vanguard series highlights cadets of Virginia Military Institute who exemplify promise, perseverance, and the true spirit of leadership. While they may not be the top-ranking students or those in prestigious positions, these individuals’ dedication, resilience, and growth embody the essence of being a VMI cadet. By sharing their stories, including the challenges they’ve faced and overcome, we shine a spotlight on the diverse paths to success at the Institute, proving that leadership and excellence come in many forms.   

When Diego Henao Ospina ’28 first considered life after high school, he weighed several paths within the armed forces. Enlisting seemed like a possibility, but advice from others who knew Virginia Military Institute helped shift his focus.  

A former Navy pilot whose son attended VMI spoke highly of the Institute, and soon after, a graduate from his own high school — now a 2nd Class cadet — returned for a recruiting visit. The way that cadet carried himself, sharp in his uniform and confident, left a lasting impression on Henao Ospina. 

Entering the Institute, Henao Ospina began as a history major. He enjoyed his time in the history department but found more of an interest in economics and business. He also plans on commissioning into the United States Air Force.  

“I’m very thankful to the history department. I really enjoyed it. But ultimately, I want to do something in the management sector, whether it’s logistics in the military or in the civilian world,” he explained. “Once I get out, I want to get into the corporate world. And economics, in my opinion, has always had that right amount of math where it’s very applicable.” 

Choosing the Air Force as his branch was another intentional decision. Many of the service members he spoke with before VMI were Air Force officers and enlistees, and he admired the long-term career paths available.  

“The Air Force seems like the best career,” he said. 

At VMI, he describes himself as a steady student — disciplined in habits, punctual with work, and willing to seek help when needed. Asking for help wasn’t always easy. He said at first, he resisted asking for help, but by the end of high school, he had learned that leaning on others could make all the difference.  

“There’s nothing shameful in that,” he said. “My main advice that I would give others is to seek help when they need it.”

As a cadet, he holds himself to high standards, striving to lead by example and instruct others. In Hotel Company, he serves as an alternate cadre corporal, managing an Old Corps squad during inspections and accountability checks, and assisting with rat training events. For him, the role was about belonging and contributing to the company that gave him his first sense of identity at VMI. A conversation with one of his own cadre corporals during the Rat Line solidified that calling.  

“That sense of belonging really impacted me,” he said.  

The journey hasn’t been without challenges. He admits that time management has been one of the steepest learning curves. Balancing academics, military duties, and the personal tasks of daily life, from making phone calls home to working through difficulties outside of VMI.  

“It can be overwhelming,” he shared. To cope, he leans on his mother for advice and strength, and grounds himself in his faith. 

Over the years, he says he’s grown vastly as a cadet. From struggling with basic drill movements on Matriculation Day to embracing the philosophy that “you get out what you put in,” he’s learned to see VMI as a system that rewards effort and resilience. Each duty — academic, military, or personal — has become an opportunity for improvement. 

Mentorship has also shaped his time. Col. John Cerkey from the Department of Modern Languages and Cultures has been a guiding influence since his rat year, both in the classroom and in supporting his ambitions to pursue a summer research project.  

Cerkey said he first had Henao Ospina in a literature class that focuses on Medieval and Renaissance Periods. 

“This was his first semester, rat year. These two literary periods are very challenging, and for most students, it was the first time that they had been introduced to literary and/or analytical techniques,” Cerkey explained. “With all the pressures that rats already have, Diego was outstanding. He, as well as the others, had to absorb and implement these new ways of thinking— he accomplished this to a superlative degree. He demonstrated originality of thought and clearly invested the effort to strive for excellence in this process. The result was that he was far and above, the best student in the class.” 

Born in Colombia, Henao Ospina eventually moved to the U.S. with his mother. He has faced several challenges, but Cerkey pointed out that Henao Ospina was able to overcome a lot.  

“Diego has remained focused and dedicated to achieving the goals that his education is making available to him. He doesn’t complain; he embraces all his challenges, crosses, and trials, with a good heart,” Cerkey said. “And at the center of his good heart, is his unwavering dedication to his Catholic faith, which strengthens him in his daily challenges, and keeps him Christ-centered.” 

Looking back, Henao Ospina sees VMI not as a finished process, but as a constant evolution.  

“You get out of the system what you put into it, and then you’re growing every day,” he said. “From the way I see it, it doesn’t end. It evolves. And it’s an opportunity to just continue learning, continue growing, despite the difficulties. The system is going to push you through difficulties, because there’s room for improvement.”