You and Whose Army?

Lt. Col. Jason Dempsey ’08GSAS takes on conventional wisdom about politics in the military.

by Paul Hond Published Fall 2010
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He coached an intramural team at the Academy, boxed with guys who had come up from Fordham and other schools. In his last match he got his nose broken, but kept going and won the fight, finishing his senior year 4–0. He credits the sport with helping him develop physical and mental courage.

“Boxing has a very real element of danger, and requires control, which is very much like life in the Army. It’s about keeping your cool.”

That would come in handy soon enough.

Culture Shock

Dempsey has a deep voice and speaks with a raspy drawl that belongs more to the military than to a specific region, an intonation that seems to have been formed within the scratchy frequencies of a two-way radio. He grew up on Army bases in the U.S., West Germany, and South Korea. His father, Jack, was an Army officer who did ROTC at the University of Idaho. When Dempsey was 14, Jack took a job with the National Guard, and the family moved to Jefferson City, Missouri. For the first time, Jason was in a fully civilian environment. He attended a public high school, where he saw racial conflict that was foreign to his experience on the base. “Overall,” he says, “it felt like I’d been transported back to the 1950s,” and not in a Howdy Doody kind of way. He took up wrestling and wondered how he’d pay for college. Maybe he’d do ROTC, like his dad.

Dempsey on patrol in Logar Province, Afghanistan, in August 2009. / Matthew ShermanOne day in English class, a friend said that a recruiter from West Point was down in the office. Dempsey, happy to get out of class, went to check it out. West Point had never really occurred to him. His conception of military academies owed much to the 1981 movie Taps, which climaxes in a fatal shoot-out between cadets and National Guardsmen. The recruiter then gave him a brochure claiming that the typical incoming class at West Point was chockfull of varsity lettermen, academic hotshots, and class presidents. That sounded good to Dempsey. Those were his kind of people. West Point it was.

He found the Academy tough at first — he wasn’t used to having every minute of his day accounted for. But by his third year he’d developed a real attachment to the place, and even began to look forward to returning there after weekends away. This was in the early 1990s, when many senior officers had already become overtly partisan. Contempt for Bill Clinton, who hadn’t served in Vietnam, was the logical extension of a pro-Republican trend that began in the Carter years, took off during the Reagan defense buildup, continued through the morale-boosting Gulf War under Bush One, and nearly burst its seams when Clinton implemented “Don’t Ask, Don’t Tell” in 1993.

Dempsey graduated in ’93 with a degree in political science, and began his military career at Fort Bragg, in the 82nd Airborne Division, as a platoon leader. Then he went to Fort Lewis, Washington, to serve in the 2nd Ranger Battalion, and after that, spent a year with the Marines at Quantico, Virginia. Then it was south to Fort Stewart, Georgia, where he was company commander in the 3rd Infantry Division. As he finished up his command, he applied to teach at his alma mater. West Point accepted him, but first he would have to go away for a couple of years, on the Army’s dime, and get his advanced degree.

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