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There were, in this country, two men—both U.S. citizens, both born to secular Muslim fathers who came to the U.S. in pursuit of educational opportunities, and one-time residents of Manhattan—who went on to drastically different futures that ultimately altered the trajectory of America’s war on terror.

One was President Barack Obama. The other was Anwar al-Awlaki, the American imam killed by an American drone.

New York Times reporter Scott Shane captures both stories in his compelling narrative Objective Troy: A Terrorist, A President, and the Rise of the Drone. “What drew me to this subject,” Shane explained during a discussion of his book at ������Ƶ, “is still being bothered that I really didn’t understand what makes somebody devote his life to killing hundreds of innocent strangers.”

This question is particularly pointed with regard to Anwar al-Awlaki. Initially a Muslim-American success story, al-Awlaki lived a seemingly happy life as an imam at several American mosques after his graduation from Colorado State University in 1994. In fact, following the terror attacks of September 11, 2001, the American media took notice of his moderate message and informally selected al-Awlaki to represent the voice of moderate Muslims, and to explain Islam to a tragedy-stricken—and angry—nation.

“The media pounced on him because everybody was looking for somebody who could explain and articulate questions about Islam, questions about al-Qaeda,” Shane said, citing an old column in his own newspaper that said, “At 30, he is held up as a new generational Muslim leader, capable of merging east and west.” He was described similarly on NPR and other prominent news outlets. However, for reasons that are still contested, over the course of eight years, Awlaki would choose to propagate a different message—one of malice toward his country of birth.

In al-Awlaki’s infamous March 2010 video, he attempted to sow distrust in Muslim-Americans and their communities, stating, “…you cannot count on the message of solidarity you may get from a civic group or a political party, or the words of support you hear from a kind neighbor or a nice co-worker. The West will eventually turn against its Muslim citizens.” In the al-Qaeda propaganda video referenced as the Call to Jihad, al-Awlaki outlines two options for western Muslims: hijra or jihad. “You leave or you fight.”

As Awlaki was evolving—or perhaps, regressing—in his stance on religious terrorism, Obama was simultaneously altering his position on how to combat this particular order of violence.

In the weeks leading up to the Call to Jihad, al-Awlaki had been conspiring with Umar Farouk Abdulmutallab—who is now better known as the “Underwear Bomber”—–to ruin Christmas nationwide by detonating a bomb over Detroit on December 25, 2009. With the failed bombing attempt, evidence of al-Awlaki’s transformation from inciter of violence to director of terror plots, and his presidential legacy on the line, Obama moved to begin a legal review as to whether it would be constitutional and legal to kill an American citizen without trial. The answer from the Justice Department was yes, and Anwar al-Awlaki went on the “kill list” on February 5, 2010.

Al-Awlaki was killed in a drone strike in Northern Yemen on September 30, 2011.

Some said that Anwar al-Awlaki was a catalyst for change in the thinking of President Obama, a former constitutional law professor who had been elected on an anti-war ticket, and who had just authorized the first assassination of an American citizen since the Civil War.

Shane, however, disagreed with the idea that Obama altered his original position or platform.

“I found it less of a transformation than people understandably suspected,” Shane mused. “Obama famously, in coming out against the Iraq War in 2002… he said, ‘I’m not against all wars, I’m against dumb wars,’ and I think he had very much come to see the Iraq War and the war in Afghanistan as dumb wars.” He continued, “For a guy like him, I think he is very much not an ideologue… he’s a pragmatist, I think, at heart. He saw this weapon [the drone] as the right answer to the terrorism problem.”

And as for al-Awlaki’s transformation? There exist two competing narratives about his radicalization: He was an al-Qaeda operative all along, or he was radicalized by the U.S. government’s relentless pursuit of him following 9/11. There is substantial evidence to support both claims.

Documents released courtesy of the Freedom of Information Act reveal that Anwar al-Awlaki had been under FBI investigation since the late ’90s, when it was discovered that he had been visited by two suspected extremists and was loosely affiliated with an al-Qaeda charity. This investigation never produced charges. Neither did a second investigation trying to link al-Awlaki to the September 11 terror plot because of his connection to two hijackers. The most criminal activity law enforcement could produce was his predilection for sex workers, which the FBI used in their unyielding pursuit and surveillance of him.

Shane believes that this last point is what initiated al-Awlaki’s radicalization. Shane explained, “One of the escort service managers he had been a client of called him up and said the FBI was just here, and they know everything you’ve been up to and they’ve talked to the women and so on. And he panicked and left the U.S.” He traveled to the United Kingdom where, according to Shane, terrorism rhetoric was more accepted at the time than it was in America. “The level of radical rhetoric was much higher, and he began to get a lot of positive feedback for taking a more radical line.

“From there [he went] to Yemen, where he was hounded around by the government, partly under pressure from the U.S., and locked up for 18 months, and shortly after that… he told his brother at some point… I’ve changed my mind about 9/11. Now I think it was justified.”

Of course, the evolution of both men could simply be a matter of circumstance. Perhaps al-Awlaki’s actions were a reaction to the crimes he felt were committed against him. Likewise, Obama’s authorization of al-Awlaki’s murder was clearly brought on by al-Awlaki’s crimes committed against humanity. Nonetheless, Anwar al-Awlaki’s radicalization and Obama’s subsequent embrace of targeted killings—even against Americans—reveals itself as an important narrative to future generations for understanding the war on terror. It is a human narrative, one of American lives given—and taken—for a cause.