Khan was born in Saudi Arabia and raised from the age of seven in Queens, New York. He was a normal city teenager who listened to hip hop and wore baggy clothing.
Even before his family relocated to Charlotte, North Carolina in 2004, however, Khan had begun to take an interest in Islam. He ditched his baggy pants for jalabiyas, the long white robes traditionally favored by Saudis. He joined two Islamic groups, but neither espoused violence.
But with the move south, Khan took a turn towards radicalism. In 2004, after watching online videos of suicide bombers blowing themselves up at American military checkpoints in Iraq, Khan began to openly support Osama bin Laden and Al Qaeda and to express that support on-line.
In 2007, shortly after Osama bin Laden released a communiqué, the New York Times reported that Khan, who had launched a blog called "A Martyr, God Willing" in Arabic, praised the al Qaeda leader, and beseeching Americans to "take his message with great seriousness."
In one of his only interviews, Khan told the New York Times that his favorite online video showed a suicide bomber striking a US base in Iraq.
"It was something that brought great happiness to me," Khan said.
Khan spent years in his parents' Charlotte basement blogging, posting al Qaeda messages, and becoming increasingly radicalized by the war in Iraq. His blog's popularity rose as his rhetoric became more extreme.
In 2009, he started a precursor to Inspire called Jihad Recollections, saying, "We have decided to take it upon ourselves to produce the first jihadi magazine in English." In the third issue, amidst calls for jihad and attacks against non-Muslims, Khan devoted space to a gushing review of a product dear to the hearts of American jihadis and infidels alike, Apple's iPhone 3. According to Khan, iPhone was "quickly becoming a standard as opposed to just another phone. With over 35,000 applications available, it becomes a joke when we hear about the so-called 'iPhone killers'."
According to Oren Segal, a researcher at the Anti-Defamation League who has followed Khan's online rhetoric since 2004, Khan left the U.S. for Yemen in October 2009, which is around the time the fourth and final issue of Jihad Recollections appeared. In Yemen, he launched "Inspire," and after his arrival in Yemen, say U.S. authorities, his on-line efforts had been in conjunction with AQAP.
Inspire's second edition, which was published before the October 2010 printer bomb attempt and included Khan's claim to be "Al Qaeda to the core," featured a photo of the Chicago skyline, which U.S. intelligence and law enforcement officials think was a tip-off of the terror group's intention to address the bombs to Jewish targets in Chicago.
"He's a model of what Americans can do in the propaganda sphere," said Segal.
"He's what's next. His message resonates and appeals to Western audiences."