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A Few Good Men

And how the U.S. military lost them.

Chip Somodevilla/Getty Images
Chip Somodevilla/Getty Images

In the late-90s, Tim Kane was an Air Force vet turned software entrepreneur, and he was surprised to find himself surrounded in the start-up business community of Southern California by fellow veterans who exchanged stories of their times in the service like secret handshakes. The more he thought about it, though, the more it made sense. The military, at its best, is a talent incubator designed to produce leaders — and a leader in the military has transferrable skills to be a leader in the private sector. Since then, Kane has gotten a doctorate in economics and come back with the statistics to back up his hunch. His numbers also show a problem for the U.S. military: The best and brightest in the services aren’t playing the military’s game anymore. They’re leaving, and in droves, over frustrations with a personnel system that is tantamount to "coercion," in Kane’s terms. Here are some examples:

Matt Kapinos

Kapinos graduated from West Point at the top of his class shortly before September 11, 2001. He deployed to Afghanistan, then Iraq, where he chafed at his superior officers’ distaste for counterinsurgency strategy. He left the military in 2006 at the rank of captain and returned to school — law school at Georgetown University. He’s not alone. The military’s retention crisis is in sharp relief at the captain level. Five years after graduation, only 58 percent of West Point’s class of 2002 were still on active duty, despite being on a fast-track for success. As of 2007, the military could barely meet its requirements for promoting captains to majors, so many were leaving. Kapinos, for his part, became disillusioned. "I was a true believer at West Point," he told an interviewer for a profile in Washington Monthly. "I thought I was going to be a four-star general." Kapinos graduated from Georgetown’s law program in 2010 and now works for an international law office in Virginia.

Dick Hewitt

While the issue of retention is most acute at the rank of captain, it extends higher as well. In "An Army of None," an FP excerpt from his book, Bleeding Talent, Kane tells the story of Dick Hewitt. A 1984 graduate of West Point, Hewitt was promoted early to major. "At that moment," Kane writes, "Major Hewitt was a prime candidate to serve as a general officer someday, maybe even lead the army." He had "checked all the boxes: one year on division staff, one year as battalion ops officer, and so on." Instead, he left the military after declining an assignment in South Korea that he felt would tear apart his family; the Army lost a promising officer to its own inflexible personnel system. Hewitt is now president of a wealth management firm in California, which he cofounded with an Air Force veteran.

Doug Webster and Scott Waddell

Three years after graduating from Yale and entering the Air Force through ROTC, Webster was named the top intelligence collector in the military in 1994, but the next year, he and another young captain, Waddell, were leaving for the private sector. "They were only captains and NCOs, nonpilots besides, in a service that was a virtual caste system," writes Kane. In other words, they had come to a dead-end. So they left and founded WheelGroup, a start-up cybersecurity business when public Internet was still in its infancy. Three years later, WheelGroup was acquired by Cisco for $124 million. To Kane, Webster and Waddell’s transition is a natural choice. The characteristics of successful military leaders are the same as business leaders and entrepreneurs — they are "innovative, risk-taking, rebellious, adaptable, persistent, opportunistic, and highly intense," Kane argues. In the retention crisis, the military’s loss is the private sector’s gain, and many Fortune 500 companies have noticed and begun campaigns to recruit veterans.

John Nagl

Nagl served a twenty-year career in the U.S. Army, rising to the rank of lieutenant colonel. In that time, he jumped from West Point to Oxford, from Iraq (twice) to Fort Leavenworth, Kansas. When Gen. David Petraeus set about revising the military’s counterinsurgency doctrine, he tapped Nagl to coauthor the revised field manual, which had been the subject of Nagl’s doctoral thesis. To many, including the U.S. Army and Nagl himself, his is a full and distinguished career in the military. To Kane, though, Nagl is a model of the talent that the U.S. military has failed to recognize and, as a result, lost; he is a case study of Kane’s argument that, though the military excels at producing leaders, it is inept at managing them. "I think John should be running the Pentagon with a handful of stars on each shoulder," Kane writes. Instead, Nagl ran the Center for a New American Security, a defense policy think tank, for three years, before taking a brief stint at the U.S. Naval Academy. Next July, he will become the new headmaster of the Haverford School, an exclusive prep school in Pennsylvania.

Paul Yingling

Nagl is not the first high-profile Army vet to go into education. Paul Yingling, who served three tours in Iraq since 2003, rose to prominence after the publication of his article, "A Failure of Generalship," in 2007 when he was a lieutenant colonel. His criticism of the Army’s flag officers made him a bold dissenting voice within the military, prompting then-Secretary of Defense Robert Gates to voice his satisfaction that "the Army’s professional journals allow some of our brightest and most innovative officers to critique — sometimes bluntly — the way the service does business, to include judgments about senior leadership." The endorsement of the secretary of defense didn’t get Yingling far, though. His next assignment had him commanding a battalion guarding detainees in Iraq, and he would later become a professor at the Marshall European Center for Security Studies. He eventually was promoted to colonel in 2011, and soon after announced that he would leave the Army to teach high-school social studies in Colorado. He’s not alone. Yingling transitioned to his new career with the help of Troops to Teachers, an organization devoted to veterans in education.

J. Dana Stuster is a policy analyst at the National Security Network. Twitter: @jdanastuster

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