Though he wasn't born here, probably the best answer to your question is Matthew B. Ridgway, who parachuted into France in 1944 and turned around the American war effort in North Korea. As if that wasn't enough experience with restive locals, he moved to Pittsburgh in 1955.
Ridgway was a native of Virginia -- but since his father was an Army colonel, the family moved around a lot. Before he settled down in Fox Chapel, he'd won just about every military commendation possible and earned a reputation for being the shrewdest American general since Civil War General Stonewall Jackson ... with the added benefit of fighting, unlike Jackson, for the right side.
In Word War II, Ridgway commanded the storied 82nd Airborne Division, one of the military's elite units. He led its attack on Sicily and its parachute drop into France during the D-Day invasion, and throughout these campaigns was noted for his tactical brilliance and personal bravery. Very personal bravery, it seems. "He'd stand in the middle of the road and urinate," one of his World War II contemporaries told David Halberstam in his book The Fifties. "I'd say, 'Matt, get the hell out of there. You'll get shot.' ... He was defiant. Even with his penis he was defiant."
Perhaps the Freudian overtones of this vignette are best passed over, especially as his nickname during the Korean War was "Iron Tits." According to a 1993 Post-Gazette obituary, the nickname derived from Ridgway's habit of carrying a hand grenade taped to his chest everywhere he went. Ridgway had actually suffered a heart attack in 1945 -- I guess being a general in World War II is kind of stressful -- but refused to be relieved of his duties. And he remained the polar opposite of an armchair general.
When Ridgway took over in the winter of 1950-51, the Chinese had rolled back much of its military advance. But Ridgway slogged along the trenches with his men, and inspired a demoralized army through sheer force of his example. Shortly after his arrival, the U.N. forces launched an offensive that pushed the North Koreans back to the 38th parallel in two months. By then, Ridgway had been put in charge of the entire war effort: President Harry Truman had canned Douglas MacArthur for insubordination, and for publicly calling for an all-out effort to wipe North Korea from the map.
The war continued for two years after Ridgway's offensive, but the successful advance forced North Korea and the Chinese back to the bargaining table. Equally important, it convinced American war planners that nuclear weapons would not be necessary to win the war, as some believed at the time.
Perhaps as impressive as his exploits on the battlefield, though, was Ridgway's judgment about a battle that shouldn't be fought. Halberstam writes that as Eisenhower was contemplating military intervention in Vietnam, Ridgway was one of the most strident opponents of getting mired in the conflict. Ridgway "was unalterably opposed to ... the implication that wars could be fought quickly, easily, and antiseptically." In fact, Ridgway "sent a team of planners to Vietnam to find out what victory would take in terms of manpower. ... No one ordered the Ridgway report; he did it on his own because of a profound conviction that if you were going to send young men into battle, you had better know exactly what you were getting into." Partly on Ridgway's recommendation, President Eisenhower decided not to step up American military commitment in Vietnam, though as Ridgway would later note, Lyndon Johnson wasn't as good a listener. Ridgway had almost unlimited success in warfare, and yet never forgot that there are limits to what warfare can accomplish. It's too bad there aren't more in Washington like him today.
Ridgway himself worked in Washington for a few unhappy years. As Army chief of staff during the 1950s, he later recalled, he spent most of his time "defending the U.S. Army from actions by my superiors." Ridgway moved to Pittsburgh in 1955 to be the head of the Mellon Institute, which at the time was a center for industrial research. (His work here is commemorated by the fact that Pitt's Center for International Security Studies is named after him.) He also joined the boards of several local corporations, and lived out his retirement in Fox Chapel.
MacArthur was wrong -- old soldiers do die, eventually. (And McArthur's drawing the Chinese into the Korean War wasn't such a bright idea either.) Ridgway died of heart failure in his home in 1993 at the age of 98: It only took his bad heart 48 years to catch up with him. He was buried at Arlington Cemetery, and his eulogy was delivered by none other than Colin Powell, who was then chairman of the Joint Chiefs of Staff.