Signing a nondisclosure agreement, he spoke daily with the FBI, passing along the chats he was handling, the leaks that were in negotiation. And, as he told the FBI, there were big ones to be had, courtesy of Sabu. As they were getting the Stratfor files from LulzSec, Siggi had heard that Assange was trying to get Sabu to join the WikiLeaks team. "Did J say anything about recruiting you permanently?" Siggi asked Sabu in one chat.
"Well he emailed me once but we didn't get to talk," Sabu replied. "Guess he's been busy/careful or whatever but let him know we have intercepted 92GB of mails from .gov.sy so this can be one of the biggest leaks in history." In November 2011, Sabu began passing excerpts of this data, later published by WikiLeaks as the "Syria Files," to Siggi – 2 million internal e-mails, going back to 2006, from companies, politicians and ministries in Syria. According to Siggi, when he told Assange about the new information, "He said, 'OK, cool,'" Siggi recalls. "'They can upload it.'"
But Siggi's spy work was jeopardized that same month when he got an angry call from WikiLeaks' spokesman Hrafnsson, accusing him of embezzling $50,000 in proceeds from selling WikiLeaks merchandise online. Siggi insists that he had run the money through his account with Assange's permission, and that any extra cash went to cover his own expenses. With both sides warring, it isn't clear whom to believe. But even if Siggi was guilty, the accusations raised more questions about why the boy, whom the group says had no role in the organization, had access to such funds in the first place. Hrafnsson threatened to report him to the police. Siggi e-mailed the FBI telling them the news. "No longer with WikiLeaks – so not sure how I can help you more. Sorry I couldn't do more :("
To his surprise, the FBI still had more work for him. Shortly after WikiLeaks published the Stratfor files in February 2012, Siggi was flown to Washington, D.C., where he met with members of the CIA, the DOD and the FBI at a Marriott hotel. The questions became dizzying: They wanted to know about others besides Assange – Jónsdóttir, Hrafnsson and more.
It didn't take long for the hammer to fall. On March 5th, LulzSec hacker Jeremy Hammond was arrested for hacking the Stratfor files leaked to WikiLeaks (he'd later be sentenced to 10 years in prison). The next day, Kayla, the LulzSec hacker Siggi had conspired with, was indicted on conspiracy charges – and revealed to be a man, 25-year-old Ryan Ackroyd, from England. But the biggest shock came when Siggi read in the news that Sabu was an FBI informant, and had been since June 2011. It suddenly all made perfect sense. For months, he had been informing the FBI of his conversations with Sabu, and they hadn't seemed to care. And since Sabu had been an informant during the time of the Stratfor and Syria files, that meant something incredible: The FBI had been well aware of the Stratfor and Syria hacks all along, and done nothing to intervene. Their target had always been Assange. The biggest and most famous hack in recent years was a carefully built plot by the FBI to snare a man it considered as an enemy of the state.
"Ultimately, the FBI's mission is to apprehend criminals and prevent the commission of serious crimes," says Glenn Greenwald, the journalist whom Edward Snowden leaked NSA files to last year. "In this particular case, they purposely allowed the commission of serious crimes they could have easily stopped. To treat an American firm like Stratfor and the privacy of Syria as sacrificial lambs in a campaign to entrap Julian Assange into criminality is unbelievably radical – you can even say corrupt."
During a meeting in Denmark in March, the FBI had Siggi sign over eight hard drives containing his WikiLeaks files. When Siggi asked them about Sabu, the agents just smiled and gave him $5,000 to cover his cost of living, then sent him on his way. He never heard from them again.
In January 2013, Siggi watched TV in horror as Hrafnsson told a reporter how he had learned the previous summer that the FBI had come to Iceland to secretly interview someone about WikiLeaks – he just didn't know who it was. But after meeting with Ögmundur Jónasson, who had just left the position of Iceland's Minister of the Interior, he pieced together that Siggi was the one who had gone to the FBI.
I met with Jónasson, who told me how, in June 2011, Iceland received a warning from U.S. authorities of "an imminent attack on Icelandic computer systems." Two months later, Jónasson found out that a plane full of FBI agents had arrived in Iceland for another purpose: to investigate WikiLeaks. Because they didn't have authorization for this, he turned them away – only to find out later that they had taken Siggi to Copenhagen. "I still have suspicion," he says, "that this was part of an attempt to put a case against Julian Assange."
Hrafnsson remains just as outraged, though he tells me he and Assange weren't shocked. "We have stopped being surprised about anything," he says. When I ask if Assange feels betrayed by Siggi, Hrafnsson arches his brow. "Inherently in your question is the assumption that there was a very close relationship, which I never saw."
While Assange remains holed up in the Ecuadorian Embassy in London, Siggi faces the repercussions of coming clean. Among other things, for the first time in this story, he's admitting to the Milestone leak. "It's probably going to lead to my conviction," he says. "But I just have to face that." In the meantime, in addition to unrelated fraud charges, he's appealing his sentence of eight months for sexual misconduct. Siggi claims the victim's father pressed the charges after learning of Siggi's relationship with his son; Siggi calls his homosexual tryst a "phase."
As for WikiLeaks, should he ever get asked one day to testify against Assange, Siggi isn't sure whether he will comply. He knows that he betrayed his former mentor and friend. But he says he did it all for the very same reasons he believed in WikiLeaks and Assange: "The truth needs to come out."
This story is from the January 16th, 2014 issue of Rolling Stone.
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