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Remarkably, Iraqi dictator Saddam Hussein chose that moment to swim against the liberalizing tide of history by invading Kuwait in the summer of 1990. As part of the 3rd Armored Division, Dempsey took part in Operation Desert Storm, which in a matter of days in January 1991 expelled the Iraqi Army from Kuwait. As part of a Cavalry unit, Dempsey helped spearhead a “left hook” maneuver that sealed off the path of retreat for vaunted Republican Guard units, which were methodically annihilated in the desert. At the time it was tempting to believe that unprecedented power might end the 20th century scourge of state-on-state aggression.

“There was a moment when the fighting was over when those of us who thought about war, and the future of warfare, kind of realized that we had become so good at that form of high-intensity maneuver that it was almost inconceivable that anyone would try and fight us that way again [on a conventional battlefield], or attempt to match that capability,” Dempsey recalled. “I mean, why would you? So I felt at the time that we had better start thinking about how others might interpret that overwhelming victory, and make adjustments in their own approach to warfighting.”

A decade later, then-Maj. Gen. Dempsey witnessed the realization of those fears, once again in Iraq. He was commanding the 1st Armored Division in Baghdad in April 2004. Just a year earlier the Air-Land Battle doctrine and American style of high-intensity maneuver warfare that proved so devastating in the 1991 Persian Gulf War had found its purest expression in the “shock and awe” campaign of Operation Iraqi Freedom, which toppled the Saddam Hussein regime and captured Baghdad in just three weeks.

The problem for Dempsey and other division commanders was that the swift victory had left U.S. forces as strangers in a strange land, stranded in the murky ground between all-out combat and a shaky peace. Civilian bosses had failed to give them a clear concept of what political outcome constituted success, and they lacked the cultural understanding to reliably discern friend from foe. Nor did the U.S. military have a doctrine to guide them to an exit from what was fast developing into a counter-insurgency quagmire.

Dempsey’s 1st Armored Division and the roughly 35,000 troops under his command were trying to keep a lid on the largely ungoverned megatropolis of Baghdad, with its population of roughly 7 million people, when the pot boiled over in April 2004. Seemingly spontaneous uprisings began to ignite across Iraq, first in the Sunni stronghold of Falluja, west of Baghdad, and then in the southern Shiite cities of Najaf and Karbala. The rapidly escalating violence threatened to spark a country-wide uprising. At the same time, al Qaeda in Iraq terrorist bombings were rattling a shaky coalition that was a mile wide in partner countries and an inch deep in commitment.

“April 2004 in Iraq is when the lightbulb really went off for me,” Dempsey recalled. “Here we were, an Army that prided itself on being on the absolute leading edge of technology, of being able to see first, understand first, and if necessary shoot first; and suddenly we were facing these simultaneous uprisings. … We all had this moment like, ‘Wow, I just didn’t see that coming!’ That suggested that relying too heavily on technology in this era was dangerous. In April 2004 in Iraq, technology was less important than understanding anthropology and sociology and what was on the minds of Iraqis on the street.”

The select group of U.S. division and task force commanders who stared into the abyss in Iraq in 2003-4, and shared that epiphany, would form one of the most influential cliques of officers in modern U.S. history, one that would ultimately shape the wars in Iraq and Afghanistan and the future of their respective services. Besides Dempsey, other members of that unique class of wartime field commanders that went on to attain four-star status included future Central Command commander and counterinsurgency guru David Petraeus; Afghanistan commander and counterterrorism pioneer Stanley McChrystal; Army Chief Ray Odierno; Central Command commander Gen. James Mattis (Marine Corps); and Southern Command commander Gen. John Kelly (USMC).

Most of them returned to Iraq during the “surge” of George W. Bush’s second term and played influential roles in the holistic counterinsurgency and nation-building campaign that ultimately pulled Iraq back from the brink. None would forget the danger inherent in a military campaign that exceeds national will or is divorced from achievable political ends.

As one of the last of that unique group of officers to retire, Dempsey has been the keeper of those memories and lessons. As his plane took off from Berlin, he noted that the refugee crisis was causing an “awakening” in European political circles. “In that sense the current crisis harkens back to the refugee crisis of 1994, which galvanized the political leadership in Europe to accept that besides treating the symptom of refugees, they also had to address the source of the instability in the Balkans,” he said. “Today’s terrible human suffering represented by millions of refugees—which has the potential to change the politics, demographics and even cultural norms of Europe for a very long time—may convince Europe to become more involved in finding a solution to the Syrian conflict.”

Of course the Balkans wars ended in the political settlement spelled out in the 1995 Dayton Accords, and the uneasy peace it established has required the continued presence of NATO troops more than two decades after it was signed. The primary question posed at the next stop in Dempsey’s final official journey—a meeting of NATO chiefs of defense in Istanbul, Turkey—was whether, after an unsatisfactory decade in Afghanistan, the alliance has the political will and military wherewithal to contemplate a long-term commitment in the Middle East.

***

In Istanbul low-hanging clouds obscured the tops of skyscrapers on the hillsides overlooking the Bosphorus, the slate gray surface of the waterway disappearing into a misty horizon to form a blurry dividing line between Europe and Asia. The haunting cadences of a Muezzin’s call to prayer sounded from a nearby mosque, reminding all within earshot that they were in the only Muslim-majority country in the alliance. Meanwhile, a surprise visit and blunt speech by Turkish Prime Minister Ahmet Davutoglu, who spoke to the NATO chiefs of defense as they dined on the banks of the Bosphorus, drove home the point that the alliance’s southern border was besieged.

As a result of Syria’s long civil war, Turkey alone had absorbed an estimated 2 million refugees, costing the country roughly $6 billion to house and care for them. Foreign fighters, many of them from Europe, continue to travel to Turkey in order to cross its porous southern border and join the ranks of the Islamic State of Iraq and Syria (ISIS) representing an acute terrorist threat on their return to Western homelands. The fighting and instability had also shattered a fragile truce between Turkish military forces and the Kurdish terrorist group the Kurdistan Workers Party (PKK), based in northern Iraq, with a subsequent increase in Turkish air strikes and PKK terrorist attacks along the southeastern border. News that Russia has been deploying fighter aircraft and other military forces into Syria in recent weeks to bolster the regime of Bashar al-Assad further clouded an already murky conflict, with myriad competing players working at cross-purposes.