Whenever I think of H. R. McMaster, President Trump’s choice to be his national-security adviser, I picture him throwing a football with his soldiers on a muddy field outside Tal Afar, Iraq. His pale head is clean-shaven, and he has a boyish grin on his thickly lined face, as if he knows he’s in trouble but doesn’t really mind. That was in early 2006, at a dark moment in the Iraq War. Colonel McMaster had spent the first two years of the war at Central Command under General John Abizaid, trying to get their boss, Donald Rumsfeld, the Defense Secretary, to acknowledge that America was fighting an insurgency in Iraq. Rumsfeld refused to admit it, because it went against his high-tech approach to the global war on terror. He would fax McMaster pages from Che Guevara’s memoirs to prove that Iraq didn’t fit the classical definition.

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It wasn’t just a theoretical point. The war was going from bad to worse in part because the U.S. military didn’t understand how to fight it. McMaster believed that a counterinsurgency strategy—putting the focus on securing the population and bringing economic development, not just killing the enemy—could turn things around. In 2005, he got his chance to prove it: he was given command of the 3rd Armored Cavalry Regiment, whose area of responsibility included Tal Afar, west of Mosul, near the Syrian border. Tal Afar had fallen under Al Qaeda’s control, and McMaster, with about two thousand troops, retook the city.

He’d already shown himself to be a fierce battlefield commander, in the first Gulf War, when he led a tank company against Saddam Hussein’s Republican Guard—probably the most intense engagement of that short war. It was what came next in Tal Afar that distinguished McMaster as one of the leading Army officers of his generation. He sent his troops into the city and kept them there, establishing connections with local leaders and Iraqi Army units, gathering intelligence on the jihadis, providing security in the streets, and showing that the Americans—appearances throughout the country notwithstanding—were not abandoning Iraq to its warring factions.

I went to Tal Afar in January, 2006, because I’d heard about McMaster’s success, and also because I’d read his book. “Dereliction of Duty: Lyndon Johnson, Robert McNamara, the Joint Chiefs of Staff, and the Lies That Led to Vietnam,” which was McMaster’s Ph.D. thesis in history at the University of North Carolina, showed how the military's top officials failed to challenge the Vietnam strategy of their civilian leadership even though they knew it was doomed to fail. It seemed as if history was repeating itself in Iraq. In Tal Afar, I asked McMaster whether he was planning on writing a sequel. Though he was expansive in his criticisms of Administration strategy off the record, he gave me the boyish grin and said, “I can’t get anywhere close to that question.”

McMaster’s achievement in Tal Afar didn’t last after his departure, in 2006. The sectarian fighting resumed, and the place became a byword for brutal killing. In 2014, it fell into the hands of the Islamic State. Counterinsurgency had tactical successes in Iraq, and McMaster was the first to show the way, but it failed strategically because it could not resolve the basic struggle for political power between sectarian groups. As McMaster told me again and again, counterinsurgency is eighty per cent political.

The McMaster I got to know in Tal Afar was independent-minded, thoughtful, and funny. He could also be tough on his men, who did not universally love him. He was among the best the U.S. military had to offer, which didn’t keep him from being passed over for promotion to general officer two times. He only received his star on the third try because of the intervention of General David Petraeus. McMaster was too intellectually rambunctious for his own good.

For all his sensitivity to the messy politics of contemporary wars, Lieutenant General McMaster has a lot of faith in American power, especially military power. In this, he’s not unlike Senator John McCain, one of his strongest backers. McMaster's musings on counterinsurgency could sound too certain, and he sometimes acted as if the Americans in Iraq had to do everything themselves—a contradiction of the doctrine he was promoting. The lesson he took from Iraq was “Do this better,” not “Don’t do this again.” But he isn’t an ideologue, like his predecessor, Michael Flynn. I imagine that he would shake his head over the conspiracy theories about Muslims that held Flynn spellbound. McMaster trained his troops to treat Iraqis with respect, and he worked to obtain an American visa for the mayor of Tal Afar, his friend, once it became too dangerous for him to stay in Iraq. I wasn’t surprised to learn from a mutual friend that McMaster considered his new boss’s ban on refugees and immigrants from seven Muslim-majority countries to be heinous and self-defeating. Whether McMaster shared this view with Trump during their conversations last weekend at Mar-a-Lago is unknowable. (McMaster did not respond to a request for comment.) And that’s where my concern about his new job begins.

Very few of McMaster’s predecessors are remembered for their success, because it’s a nearly impossible position. The national-security adviser has to master three fundamental things. He has to stay on top of fast-moving events around the world while helping to develop long-term American strategy across regions and issues. He has to allow the views of the key national-security officials in Washington to reach the President in an honest and independent way. And he has to win the trust of the President himself, with whom—if the White House is working as it should—he will spend hundreds of hours. On the first, McMaster—though a fellow at the International Institute for Strategic Studies, in London—has little experience outside the military realm. What are his views about China, Latin America, Russia, the European Union? He has also spent little time in Washington and doesn’t know the national-security bureaucracy from the inside.

Finally, what kind of relationship can McMaster have with Trump? Will he be able to choose his own staff? Will he have the bureaucratic skill to outmaneuver the long knives of Steve Bannon and his shadow National Security Council? Will he tell Trump, as he once told Rumsfeld, what he really thinks, even if it drives the President crazy? If McMaster remains his own man, he could be a force for sanity and stability in the White House—but he also might not last long.