UVA Today

Alumnus Glenn Kirwin’s life, which ended with the collapse of the World Trade Center on Sept. 11, 2001, inspired his son Miles (right) who joined the Army and followed his father into business. (Contributed photos)

Miles Kirwin, an entrepreneur and National Guard officer, has distinct memories of that Tuesday in September, a day that started out like any other day in his hometown of Scarsdale, New York.

“I was 10 years old at 9/11 and living a pretty privileged life in Scarsdale, and it was the typical suburban upbringing – great family life, everything going well – and then it all came crashing down,” he said. 

Kirwin remembered spending time with his father each evening before going to bed, perhaps playing board games or watching the New York Knicks. That morning started normally, with Kirwin going to Quaker Ridge Elementary School, where he was a fifth-grader.

That morning, the children were told that something had happened at the World Trade Center, though at the time, Kirwin did not understand all the implications. But when a teacher told the students that it was likely all the people above the 90^th floor were gone, Miles, who knew his father worked on the 105^th floor, realized the enormity of what happened and started to cry. His mother came to the school to retrieve him and his younger brother, Troy, who then was in second grade.

“In Scarsdale, which is a small, close-knit community, we were the only family that lost anyone,” Kirwin said. “Everyone knew what happened to us and everyone knew me. I was now ‘the 9/11 kid.’ ”

Paul Kirwin, Glenn Kirwin’s father, with Miles Kirwin when he graduated from Army Ranger school in 2014. (Photo contributed by Joan Kirwin)

While Kirwin did not want the attention this brought to him, there were silver linings.

“Looking back, I don’t think I would be the person I am today if I didn’t experience that crisis at an early age,” he said. “That turned into my driving motivation in life – to join the military, base my life in New York, and be successful in whatever I do to honor his legacy.”

Kirwin knew he wanted to serve his country in some capacity by the time he graduated from high school.

“I didn’t join ROTC until my second year” at UVA, he said. “I didn’t really understand the military growing up, because no one from Scarsdale joins the military. I don’t come from a military family, and there aren’t many Jews in the military to start with.”

Kirwin was the ninth member of his family to attend UVA, and Troy (a 2016 graduate of the McIntire School of Commerce) was the 10th. His father and grandfather had been Hoos, as well as four uncles and his mother, Joan Boswell Kirwin, a 1984 graduate of the College. (His parents met on Grounds, but did not start dating years later in New York City.)

“When I got to UVA, I remember seeing the Army cadets working out together near Old Dorms every morning,” he said. “I always admired the camaraderie and discipline they showed. And it hit me toward the end of my first year, that this is what I was meant to do. So I ended up joining ROTC and fell in love with the military.”

Joining ROTC gave him focus.

“Joining ROTC filled a void I felt in my life and gave me a purpose that set me on the path I am on today. he said. “I was a very good Cadet, and much of what we were taught came naturally to me. I was more motivated than ever to learn, and I thought about 9/11 every step of the way.”

Kirwin joined the infantry because he wanted to make the biggest difference he could. 

“The infantry are the foot soldiers on the ground,” Kirwin said. “Everyone supports the infantry – from the pilots in the air, to the logistics units supporting from the rear, because at the end of the day, ground forces win wars – and I wanted to be at the very tip of the spear, where I could have the most impact.

“I also think there is no better form of pure leadership than an infantry officer, where you have no distractions such as tanks or heavy equipment assets you need to maintain. Your only assets are those soldiers, and your success is dependent on the ability to maintain their readiness and motivate them to accomplish a mission.”

The Brothers Kirwin: Troy and Miles Kirwin at the 2019 NCAA Men’s Basketball Championship. (Photo contributed by Joan Kirwin)

Kirwin’s choice was purposeful. He had a mission.

“I wanted to deploy,” he said. “I joined specifically so I could go to Afghanistan.”

With that focus, Kirwin graduated from UVA in 2013 as a Distinguished Military Graduate and a commissioned second lieutenant in the United States Army Infantry.

“After school, I spent one year in Fort Benning, Georgia, to continue my training and then three years at Fort Campbell, Kentucky, with the 101^st Airborne Division,” he said. “Every decision I made was guided by my motivation to get to Afghanistan so I can do my part in defending our country and preventing another 9/11.”

But, as Robert Burns noted, “The best-laid schemes o’ mice an’ men/ Gang aft a-gley [Go often askew].”

“I selected the First Brigade Combat Team in the 101st that was set to deploy to Afghanistan right when I graduated Ranger School,” Kirwin said. “All the cards were lining up. But, unfortunately, when I arrived at the unit, the deployment was cancelled.

“I spent the next three years looking for opportunities to deploy, but due to circumstances beyond my control – wrong place, wrong time – it never happened.”

As his time at Fort Campbell passed, and the end of his required service time approached, Kirwin knew he had a decision to make.

“As much as I hated the thought of leaving the Army without a deployment, there was so much more I wanted to do in life outside of the Army,” he said. “I wanted to try my hand at business, be back in New York, and eventually start a family,” all part of his larger plan to follow in his father’s footsteps.

Kirwin found a compromise. Having been promoted to captain, he left the active-duty Army and transitioned to the New York Army National Guard. He joined the 69^th Infantry Regiment based out of the Armory on 68 Lexington Avenue in Manhattan, the closest military base to the World Trade Center. The storied “Fighting 69th,” is responsible for providing emergency civil support to New York City and can trace its lineage back to the 1^st New York Regiment of the American Revolution.

“The 69th has been associated with New York City forever, and today we’re most known for leading the St. Patrick’s Day Parade every year.” Kirwin said. “We were traditionally a unit comprised of Irish immigrants. But today, the 69th is much more of a melting pot with a wide variety of ethnicities and backgrounds that reflect the diverse culture and make-up of New York City. My unit consists of Dominicans, Asians, Muslims, Jews, bankers, cops, teachers – people from all different walks of life.”

The Guard unit has another connection for Kirwin.

“The 69^th was were there on 9/11,” Kirwin said. “They were called up to set up a security perimeter around the site and assist with rescue and recovery efforts. Some of those same men are still in the unit today, almost 20 years later. And now I have the privilege of serving alongside them.”

While Kirwin is passionate about his military service, he is also equally dedicated to his business career. After he left the Army, he earned an MBA from the Tuck School of Business at Dartmouth College, commuting five hours back and forth to his guard unit in New York City for his drill weekends.

After Dartmouth, Kirwin moved to New York City and took a management consulting job with Deloitte, where he worked through the pandemic. He also took command of Avenger Company within the 69th, named for their mission to “Avenge” the terrorist attacks on 9/11. It was a busy time for the unit. 

“We were activated as part of New York City’s COVID-19 response, and I was responsible for setting up and managing all of the testing centers and food distribution sites in the Bronx – with around 130 soldiers. This was in late March, when the city was completely shut down and no one knew where to get tested,” he said.

After returning to Deloitte in June 2020, Kirwin’s unit was called up again in January following the insurrection at the U.S. Capitol in Washington, D.C. The 69th was one of the first units to arrive at the U.S. Capitol armed to defend it.

“My unit was responsible for part of the inner security line around the Capitol building. We rotated on 12-hour shifts patrolling the line from 11 p.m. to 11 a.m., sleeping on the marble floors of the Capitol Visitors Center when off shift,” Kirwin said. “It was a surreal experience – after eight years in the Army, this was the first time I ever loaded my rifle for the purpose of defending myself – not training.”

Kirwin stayed deployed for several weeks, patrolling the Capitol in full gear, seeing members of Congress going about their days and witnessing the inauguration of a new administration.

“Not what I imagined when I joined the Army, and certainly not what my original intent was,” he said. “But I was honored to have the privilege of leading soldiers through two critical moments in our nation’s history.”

After his stint in Washington, D.C., Kirwin returned to New York City, left Deloitte and is now working for a health-tech start-up called H1, which offers a new platform for health care professionals to connect with industry and each other. H1’s mission is to create a healthier future by connecting the health care ecosystem. Kirwin expressed his excitement in helping build a purpose-driven business from the ground up, similar to what his father did with a new business called “ESpeed” at Cantor Fitzgerald.

The 9/11 attacks that shaped Kirwin pushed him to seek out high-pressure situations throughout his life.

“I lived through the worst crisis of the 21st century and all eyes were on me from that moment as ‘the 9/11 kid,’ ” he said. “Since then, I’ve felt this innate sense of duty to seek out crises and fight my way through it.

“I think I work best in crisis-type situations and I’ve learned that I love being the man in the arena to whom people look towards for leadership,” he said. “I am excited to see where my dual military and business career take me next – and what new crises await me.”