Skip to main content

Anwar al Awlaki rose to notoriety in the 2000s as a leading internet jihadist whose lectures and videos were very popular among the emerging Islamist movement. But his history with Al Qaeda, and in particular his contacts with the 9/11 hijackers while under investigation by the FBI, pose serious questions. Was Awlaki a terrorist, or a spy, or both? Was he working for US intelligence while acting as a spiritual leader to several of the hijackers? In this episode we take a critical look at Awlaki, his life, his FBI file and why he became the first American to be killed in a US drone strike.


Documents: al-Awlaki Bought 9/11 Hijackers Tickets

I am sure you have all heard the name Anwar al Awlaki. In the immediate post-9/11 years he was everywhere – apparently setting the world ablaze by posting videos on youtube. In some ways he was a prototype for ISIS, a postmodern terrorist who existed largely through media rather than through violence. To this day there is no evidence that he directly killed anyone. Nonetheless, he did help inspire a new generation of jihadists to embrace the cause, or die trying.

I think he is a very important figure in the history of Al Qaeda who connects to many of the people and events we’ve looked at so far. To whit, a brief biography. Anwar was born in New Mexico in 1971, the son of Nasser al Awlaki, a Yemeni immigrant who became Fulbright scholar who went on to serve as Yemen’s Agriculture Minister. Young Anwar came from a well-off middle class family, like many of the people we’ve encountered in this series. His family moved back to Yemen when he was 7 years old, but in 1991 Anwar was back in the US, studying for a Civil Engineering degree at Colorado State university.

Bizarrely, he claimed to be born in Yemen, even though he was a US citizen by birth. In 1993, while he was a student, he visited Afghanistan and trained with mujahideen. He returned to the US after a brief period and reportedly showed an increased interest in religion and politics, even convincing one young man to go to Bosnia to join the mujahideen. In the Al Qaeda story, all roads lead to Bosnia.

From 1996 to 2000, Awlaki was the imam of the Ar-Ribat mosque in San Diego California. He was approached in the late 90s by Ziyad Khaleel, an Al Qaeda facilitator who bought one of Bin Laden’s satellite phones. They were both involved in a Yemeni charity called the Charitable Society for Social Welfare. Much like other charities we’ve looked at, this was later identified as a front for laundering money for terrorism. Awlaki also met with an associate of the Blind Sheikh during his time in San Diego.

So it was no surprise that from June 1999 to March 2000 the FBI investigated Awlaki, spending most of their time interviewing prostitutes he’d picked up around the San Diego naval base. I’m not kidding, if you read his FBI file you’ll find page after page of 302s of interviews with hookers, many of whom were not flattering about Anwar’s sexual stamina.

Anwar was evidently a friend of Omar Al Bayoumi, the Saudi intelligence agent who helped Nawaf Al Hazmi and Khalid Al Mihdhar when they first arrived in the US in January 2000. The pair moved from Los Angeles to San Diego in February 2000 and began attending Awlaki’s mosque. Some reports say he had lengthy private meetings with the two, suggesting he knew about or possibly was involved in the 9/11 attacks.

But only a few weeks after they made contact, the FBI shut down their investigation into Awlaki. Some reports say the FBI’s conversations with the prostitutes had got back to Anwar, and he was on to them. Awlaki then resigned from the San Diego mosque and took a sabbatical, travelling to various countries. By this point his sermons had made him quite famous, though he didn’t preach extremist, hateful or violent material. He went back to the US once more, settling in Falls Church Virginia, in January 2001. He became the imam of a local mosque, and re-established contact with Nawaf al Hazmi, and apparently Khalid Al Midhar and Hani Hanjour as well. That’s three of the five men who apparently crashed a plane into the Pentagon.

Bear in mind Falls Church is less than 7 miles from CIA headquarters, less than 8 miles from the Pentagon, just 10 miles from FBI headquarters, less than 40 miles from the headquarters of the NRO and the NSA. Falls Chuch is basically in the middle of the entire US intelligence community – the headquarters of the CIA, FBI, NSA, DIA, Office of Naval Intelligence, the Army’s Intelligence and Security Command, even the headquarters of the National Geospatial Intelligence Agency – all within an hour’s drive or so. Is this not a strange place for a radical imam to be meeting with would-be terrorists? If there’s anywhere within the US where you’d think people who might suspect they’re being watched by US intelligence wouldn’t move to, it’s Falls Church, Virginia.

There is even evidence, in the form of a heavily redacted FBI document compiled just 16 days after 9/11, that Awlaki bought airline tickets for three other hijackers, namely Waleed al Sheri, Satam Al Suqami and Mohammed Atta. The FBI later denied that this is what the full document says. But then this is the same FBI whose timeline of the 9/11 hijackers doesn’t explicitly say they hijacked or crashed the planes, and that they had plane tickets for flights after 9/11, and that their bank accounts and credit cards were still in use after 9/11.

Indeed, Awlaki was interviewed by the FBI at least four times in the days after the attacks, and admitted having met one of the hijackers but denied knowing any of them. But it would be a coincidence of epic proportions that men he didn’t know randomly turned up at his mosque in San Diego then a year later randomly turned up at his mosque on the other side of the country. Which was right in the heart of the US intelligence community, to where these terrorists supposedly decided to move despite having no connections there, aside from Awlaki.

Though the FBI suspected Awlaki of having bought plane tickets for the people the FBI believe did 9/11, and put him under further surveillance (including more trips to pick up prostitutes), in late 2001 Awlaki was giving interviews condemning the attacks, and being heralded by the mainstream media as a moderate Muslim leader who could help bridge the gap with the rest of the Muslim world. In early 2002 he was invited to a luncheon at the Pentagon and gave a presentation that was praised by Pentagon officials, in particular how he handled heckling from the audience. This whole time he was under FBI surveillance.

In June 2002 a Denver judge signed an arrest warrant for Awlaki, for passport fraud. When he had applied for a social security number in 1992 he had written on the form that he was born in Yemen, which is stupid because if he’d said he was born in the US (which he was) he would have got the number more easily. On October 9th the warrant was rescinded, apparently due to a lack of evidence. But Awlaki was still on the watch list, so the following day he was picked up at JFK airport when he arrived back in the US from a trip to the Middle East. After the officials realised the warrant had been quashed, they let him go.

In late 2002, Anwar started writing and speaking more radically. He praised Palestinian suicide bombers, and left the US and spent quite a lot of time in the UK, preaching to hundreds of Al Muhajiroun members and the like. It is during this period that he supposedly gave a lecture that was attended by the alleged 7/7 bombers. In 2004 he settled in Yemen and became one of the world’s foremost internet jihadis, spending years issuing statements, making videos, and giving sermons trying to inspire global jihad.

Between December 2008 and June 2009 Awlaki exchanged emails with Nidal Hasan, which were intercepted by US intelligence. Though the emails show no sign of Awlaki inspiring or provoking Hasan, on November 5th 2009 (bonfire night) Hasan shot 13 people and injured over 30 others in a mass shooting at Fort Hood.

A few weeks later, on Christmas Day 2009 Umar Farouk Abdulmutallab set fire to his underwear on Northwest Airlines Flight 253 on its way from Holland to the US. Umar was apparently an associate and follower, inspired by Awlaki. Likewise Faisal Shahzad, the so-called Times Square bomber (who never bombed anything and couldn’t build bombs) said he was a follower of Awlaki and was inspired by his sermons. Ditto Roshonara Choudhry, who stabbed a former British cabinet minister. Numerous other plots have been attributed to Awlaki, perhaps the most ridiculous being the Printer Cartridge Bomb Plot, which makes no sense because the explosive was supposedly hidden on a plane and discovered after a tip off from Saudi intelligence. Why anyone would think of disguising it as a toner cartridge from a printer or photocopier is beyond me.

As the de facto head of Al Qaeda in the Arabian Peninsula, the offshoot who did the USS Cole bombing, Awlaki became an enemy of the state. In early 2010 Obama signed off on a kill order, and in July his father filed a lawsuit challenging the order. This was thrown out, and in May 2011 the US tried to kill Anwar via drone strike, but missed. On September 30th 2011 they tried again, and this time they were successful. A few weeks later his son, Abdulrahman Anwar al-Awlaki, also an American citizen and just 16 years old, was also killed in a drone strike. In January 2017, in a mission ordered by president Trump, Anwar’s 8 year old daughter Nawar was killed in a commando raid in Yemen.

In Anwar’s final article before he died, in Al Qaeda’s Inspire magazine, he said that the CIA and FBI had repeatedly tried to recruit him as an informant.

Was Anwar Al Awlaki a Spy?

The biggest, most obvious and important question about all of this is whether Awlaki was a spy. Aside from spending a lot of his time hanging around a naval base and living slap bang in the middle of the major US intelligence agencies, there are several compelling indications that he had some kind of relationship, most likely with the CIA.

Awlaki explains lying on his university application (and other documents) about being born in Yemen because, from the article in Inspire, ‘When I finished high school in Yemen I was accepted on a scholarship to study in the US. But there were two problems: I was an American citizen and these scholarships are only for foreign students and number two the scholarship was to study agriculture and I wanted to study Engineering. My father at the time was a Minister of Agriculture and the Americans were happy to make some exceptions for him.’

He went on to describe how he was approached by the Office of International Students, ‘which in my belief is a front for recruitment of international students for the government and is also a front from spying on them and reporting on them to the authorities’.

He claims that the government sent people who were obviously moles into the mosque in San Diego, and that his arrests for solicitation in San Diego were part of an attempt to recruit him. Anwar claims that in one of the meetings he had with the FBI immediately after 9/11 they tried to recruit him as a cooperator, not a spy as such but still in the ballpark.

Then there is the FBI investigations, which mysteriously stopped just at the point they might have discovered his connection to Al Mihdhar and Al Hazmi. As we explored in the 9/11 episode, these two were likely targets for recruitment by the CIA, and were helped by a Saudi intelligence agent from the moment they landed in the US. If the CIA had recruited them, or were trying to, then there’s every chance the FBI backed off Awlaki so as not to step on any toes.

Indeed, just speculating here – what if Awlaki was the man who recruited the two on behalf of the CIA? He lied about his contacts with them when the FBI interrogated him after 9/11, which is what a CIA asset would do. And even though the FBI knew he was probably lying, they didn’t charge him with anything.

When the news first broke about Awlaki dining at the Pentagon in early 2002, the media reported that the FBI only found out about this when they interrogated Awlaki following the Fort Hood shooting in 2009. At this point Awlaki was in prison in Yemen. But documents released several years later including surveillance logs show that the FBI had a special team following Awlaki 24/7, including when he went to the Pentagon. So while they may not have known that he spoke at a dinner, they knew he went to the Pentagon.

Then there’s this mysterious arrest warrant that was rescinded, because the reporting on that is contradictory. Some say the warrant was quashed the day before he was arrested at JFK airport, others say the order didn’t actually go through until the day after his arrest and Awlaki was released on the say so of an FBI agent. There are other indications in the FBI documents that they did try to recruit him as an asset, not merely a cooperator.

There’s also no evidence that the Pentagon requested any info on Awlaki before they invited him, nor that the FBI provided them any. Given that certain information is shared by default, especially for security vetting files, this seems like either an intelligence failure or the compartmentalising of information to protect an asset.

There’s also the fact that the line about him being a ‘moderate’ Muslim leader who could help build bridges appears in the documents on the dinner at the Pentagon, while pretty much simultaneously the major media were reporting the same thing. You could argue this is why the Pentagon selected Awlaki to give the speech, but it could also be about building a legend for him, so when he subsequently turned more radical it would seem real.

Of course, none of this proves that Awlaki was an intelligence asset, it’s entirely possible that he wasn’t. But that idea is consistent with the known facts, there’s nothing that proves he couldn’t have been an asset, and he fits the profile of the sort of person the CIA would try to recruit. Young, well educated, contacts through mosques to both Muslims in general and to people involved with Al Qaeda, fluent in multiple languages and capable of working in different locations and conditions. So the question becomes: if Anwar Al Awlaki wasn’t a spy, why not?

The Death of Awlaki

Anwar al Awlaki died in September 2011, along with Samir Khan the first Americans to be killed by the government via drone strike assassination. But aside from paying for sex, Awlaki had only committed speech crimes, crimes of incitement or radicalisation. These are crimes under counter-terror legislation but they would usually carry a sentence of a few years. Whether you think they should be crimes, or whether I do, is another matter. The point is that this was not only an extra-judicial murder, it was far beyond any likely sentence that would have been given to Awlaki if he’d been convicted.

Now it may be that the government lawyers found some excuse – argument, I mean argument – that somehow makes this legal. But it was quite a shock to the system, that the government could simply say this American citizen is a terrorist and therefore must die. Bearing in mind that this happened a few months after the Abbottabad raid, the government heralded it as a glorious success in the struggle against Islamic extremism.

In reality, Awlaki was mostly popular because of youtube, along with early use of social media promotion. But a year earlier all his videos had been deleted from youtube following pressure from Congress. His power was largely derived from the internet, and the mechanisms existed for eliminating or at least greatly diminishing that power. So why did they kill him?

One reason is that they’d invested so much in the legend of Awlaki. This genius orator who could inspire terrorist attacks by posting videos online. In the years where Bin Laden was either very quiet or possibly dead, Awlaki filled the gap. He was the global jihadist of choice.

Then there was the problem that people were poking into Awlaki’s activities in the US, including his visit to the Pentagon. That, and other facts about the FBI’s investigations, came out before he was killed. Then there’s the article he wrote for Inspire, claiming that he’d been repeatedly targeted for recruitment. Given that MI6 hacked Inspire magazine and replaced bomb-making formulas with recipes for cupcakes, and this was reported a few months before Awlaki’s death, we can only assume that Western intelligence knew everything Inspire was going to publish as soon as the articles came in.

Which means they knew about the Awlaki article. Which might provide a motive for his death. After all, if someone got to him and he admitted that he’d been acting as a provocateur for Western intelligence then not only would his cover be blown, it would probably see some very uncomfortable questions being asked. Plus by that point he’d served his purpose, so liquidating him was the logical choice. If you’re a psychopath.

I will say one more thing, about the Underwear Bomber Umar Farouk Abdulmutallab. According to a supposed witness who got on the plane in Amsterdam, Kurt Haskell, Umar had some sort of handler who helped him bypass security and passport checks. He describes the handler as an ‘Indian man’ in his 30s. I don’t take Kurt Haskell seriously, he has turned into a full blown conspiracy theorist who rants about Jews and all sorts of nonsense. I don’t know what he did or didn’t see at Schipol Airport, but I don’t find him trustworthy.

Nonetheless I think the Awlaki story is important because he exists at the intersection of many other problematic events, from the USS Cole bombing through 9/11 to the Underwear Bomber and beyond. While the Underwear bomb had no hope of succeeding, it happened on Christmas Day and helped remind everyone of the supposed ever-present threat of terrorism. It also helped establish the nude body cameras and the TSA gropers, in the name of checking that your balls are your balls and not a cunning bomb made of hair dye and smelling salts disguised as your balls.

As to whether he was a spy – one possibility that is largely ignored is that Awlaki was working for Saudi intelligence. He did know Omar Al Bayoumi and appears to have been part of the reception committee, the support network for Al Mihdhar and Al Hazmi, the first of the hijackers to arrive in the US. This also might explain why the FBI repeatedly adopted a hands-off posture. And why he was able to live in Falls Church for two years without much hassle from US intelligence. Though it wouldn’t explain what Awlaki was doing at the Pentagon, which is something of an anomaly. Maybe they genuinely thought he was a moderate Muslim with relevant expertise.

I hope you’ve enjoyed this alternative look at Anwar al Awlaki, and the many weird and suspicious elements to his life’s story. Certainly, he is a key figure in whatever this Al Qaeda phenomenon was, in both the second phase from 1996 onwards, and the third phase from 9/11 onwards.