I first met Eric Harroun, better known as “The American Jihadist,” over cocktails at a rooftop martini bar in one of Cairo’s Nile-side 5-star hotels. It was July of 2011, and Harroun was recovering from a recent arrest by Egyptian security forces following his involvement in the summer’s anti-military protests. The conversation was one of fervent indignation and outrage, but also one of paralyzing powerlessness in the face of impunity and injustice.

Yesterday, the same combustible combination of emotions— characterized by a tangible sense of conflict, passion, and despair—resurfaced poignantly when his sister announced on Facebook and then confirmed by phone that 31-year-old Harroun died of an overdose in his father’s home in Phoenix, Arizona. The family says the death was an accident. There will be an autopsy.

In Cairo when we met, despite his release and his return to his expat routine, Harroun clearly was shaken by what he had experienced while in Egyptian custody, and he cursed the U.S. Embassy for its alleged unwillingness to protect American citizens, like him, abroad.

Harroun presented himself as a Lebanese-American Sunni Muslim ex-US-soldier who had turned freedom-fighter, and who, like many young Westerners, had come to the Middle East to protest against corrupt American foreign policy in the region. In this initial meeting, he swung quickly back and forth between his expressions of deeply patriotic sentiment and his lamentations about his despair and disillusionment with the United States.

According to Harroun (and an FBI affidavit), he continued to travel the region in relative obscurity seeking out the tumultuous energy of the ongoing Arab Spring uprisings. In early 2013, however, he burst into the spotlight as “The American,” a social-media-happy Western addition to the armed Syrian opposition.

After arriving in Turkey in late 2012, Harroun had skipped across the then-porous border into northwestern Syria to join a militia within the Free Syrian Army. Then Harroun claimed that in the wake of a confusing firefight with Syrian government loyalists he found himself retreating alongside an al-Qaeda affiliated Syrian opposition group, Jabhat al-Nusra. Although they initially held him as a prisoner, according to Harroun and another former al-Nusra fighter, he proved himself to them in a clash with Syrian government forces by saving an injured al-Nusra combatant. “When [Harroun] saved his life, we thought he could be helpful at the very least,” recalls “Abu Mohamed,” a former al-Nusra fighter who knew Harroun while in Syria, but who has since returned to his home in Kuwait. “And then [Harroun] spilled blood for us,” he was injured in combat, said his former comrade in arms.

“When he went back to America, he thought he was going to get us weapons,” Abu Mohamed tells The Daily Beast. “I think he believed he could be a connection between us and money and weapons in America. Every time I talked to him, he wished he was back fighting Bashar [al Assad] with us.”

Abu Mohamed claims that many of the fighters became suspicious of Harroun after his detention in the U.S., but he believes Harroun was loyal to the Syrian opposition’s cause.

Harroun had been interviewed in Istanbul by the FBI, which questioned him about providing the Syrian rebels with military aid, according to the affidavit in support of the criminal complaint against him. When Harroun landed at Dulles International Airport on March 27, 2013, however, he was first voluntarily interviewed by the FBI, then arrested by U.S. federal agents on charges of conspiring to use weapons of mass destruction with a U.S.-designated terrorist organization. If convicted, Harroun could have faced a sentence of 30 years to life imprisonment.

Harroun eventually spent six months in solitary confinement in a federal prison in Alexandria, Virginia, before being released in a plea deal in September 2013.

By the time of his arrest, Harroun had already become a high-profile character in the Syrian theater—namely for his notorious Internet presence. War reporters, analysts, Assad loyalists and al-Qaeda-affiliated networks all had something to say about Harroun, whose reputation now ranged between freedom fighter, terrorist, spy, or war tourist—depending on the forum. International news reports emerged about Arizona Jones and an investigative piece in Foreign Policy, “The Jihadist From Phoenix,” depicted him as an unstable, racist, “manic” American veteran. It also exposed his past violent drunken run-ins with the law in the United States. This reporting further revealed that Harroun was not in fact Lebanese—he was a white, American Muslim convert with no previous connection to the Middle East. In fact, during his military service from 2000 to 2003, had not been sent overseas, as many had thought and as he had suggested.

This polarizing public profile positioned Harroun as an unsympathetic character as his case progressed through the U.S. courts. Yet his situation represented what his attorney, public defender Geremy C. Kamens, described as an unprecedented case in American law, adding that “never, to my knowledge, has the U.S. government charged a U.S. citizen for fighting with a group aligned with U.S. interests.”

As University of Texas law professor and national security expert Robert M. Chesney told The New York Times, “If this guy’s telling the truth, there’s an interesting question as to why we’re prosecuting him. He seems to be fighting on the U.S. side, but with the wrong people.”

During the proceedings, FBI agent Paul Higginbotham testified, that there was no evidence that Harroun was involved in terrorist activity, that they had no evidence that he held “fundamentalist or jihadist views,” and that Harroun had stated he “hated al Qaeda.”

Harroun’s case appears to have been just the beginning of legal headaches and complications for federal prosecutors. In the United States and Europe there is growing government concern that people who’ve gone to fight in Syria will bring the threat of terror home with them alongside their deep frustrations. A recent arrest reveals that the U.S. is enhancing its monitoring and restrictions on those who want to travel to Syria to take up arms: 20-year-old American student Nicholas Teausant was arrested on terrorism charges just last month on the US-Canadian border as he attempted to begin his journey.

Harroun, upon his release, returned to his provocative social media habits and contentious sense of humor; yet he spoke often of his heartbreak for the Syrian people, for what he saw as the decline of his country, and for the stress on his family.

“You’ve got to joke and laugh to keep from crying,” he wrote one winter evening on Facebook. In an interview last fall, Harroun told a local ABC affiliate that he “felt betrayed by my government, my country” and that he did not regret what he’d done. “I don’t regret trying to help people,” he said.

Harroun was anxious to return to Syria, but, as he awaited parole, he also expressed interest in enrolling in classes at his local community college.

On the afternoon of April 8, Harroun was found unconscious in his father’s home. Cari Gerchick, a spokesperson for Maricopa County, confirmed his death and announced that the Office of the Medical Examiner would begin an autopsy on today. Eric is survived by his father Darryl, his mother Shirley Ann, and his sister, Sarah Harroun.