From royal insider to target: How the Arab Spring propelled Jamal Khashoggi into the Saudi leadership's crosshairs

·Chief Investigative Correspondent
·7 min read

There are few more feared destinations in Cairo than Tora Prison — a notorious complex where hundreds of political prisoners have been jailed, often subjected to unspeakable torture.

But one day in 2008, one of the prison’s most celebrated inmates, democracy advocate Ayman Nour, figured out a way to hoodwink his jailers — and ultimately get himself freed. How did he do so? A clever ruse that Nour concocted with the active collaboration of a visitor from Saudi Arabia, Jamal Khashoggi.

Khashoggi’s role in helping Nour outsmart the jailers of Tora Prison is told for the first time in “A Revolution Crushed,” Episode 4 in the latest season of Yahoo News’ "Conspiracyland" podcast, “The Secret Lives and Brutal Death of Jamal Khashoggi.” It is a story that illustrates the Saudi journalist’s political transformation — and his penchant for inserting himself into the midst of events that rippled through the Middle East.

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Khashoggi had once been a friend of Osama bin Laden, championing his battles in Afghanistan against the Soviet occupiers. He later became a spin doctor for a harsh antidemocratic Saudi monarchy and was sometimes assigned to what one former colleague called “secret missions” to collect intelligence.

But in the years after the Sept. 11 terror attacks, Khashoggi’s views began to evolve as he became an increasingly outspoken supporter of democracy and freedom of speech.

That led him to visit Nour — a dissident whose case was so well known that multiple U.S. officials, including President George W. Bush, had publicly called for his release.

But getting in to see him wasn’t easy. Journalists were barred from Tora Prison. So Khashoggi listed himself as a relative of the prisoner’s wife.

Then, under the watchful eyes of the jailers, sitting across from each other at a table in the warden’s conference room, Khashoggi and Nour implemented their scheme.

Opposition leader Ayman Nour stands in a court in Cairo January 23, 2007. (Nasser Nuri/Reuters)
Egyptian opposition leader Ayman Nour in a court in Cairo in 2007. (Nasser Nuri/Reuters)

Khashoggi had brought with him a pack of cigarillos, or mini-cigars, that he plunked on the conference room table. Nour was ushered in and brought his own pack, placing it on the table as well, as he sat down across from Khashoggi. “When we stood up to leave, each took the other’s pack,” recalls Nour, now living in exile in Istanbul.

And inside Nour’s pack, which Khashoggi smuggled out of the prison, was an eloquent letter to Sen. Barack Obama, then a Democratic candidate for president.

Before long, the letter popped up on Obama’s Facebook page.

“Dear Senator Obama: These lines, which I'm not certain will see the light or reach you, were written behind the walls of an old prison in the south of Cairo,” the letter read. Nour explained why the charges against him by Hosni Mubarak’s government were a sham.

“The real charge is that I committed the crime of dreaming of change!” the letter continued. “Me and the generation I belong to — in Egypt and the Arab region — views you as a gifted and inspiring model for the dream of freedom. [I] look forward to hearing from you — today, tomorrow and in the future.”

The letter had an impact. In February 2009, just a few weeks after Obama’s inauguration, Nour was released from prison — a move that was widely interpreted as a gesture by Mubarak to the new American president.

Ayman Nour (c) the Leader of the Ghad Opposition Party is mobbed by supporters outside his party's headquarters following his release from prison on February 19, 2009. (Mike Nelson/EPA/Shutterstock)
Nour is mobbed by supporters outside his party's headquarters following his release from prison on Feb. 19, 2009. (Mike Nelson/EPA/Shutterstock)

That’s an amazing backstory. I wish I did know it,” Ben Rhodes, then one of Obama’s top foreign policy advisers, says on "Conspiracyland" when told about Nour’s account of his visit with Khashoggi that day.

Rhodes says he recalls Nour’s letter but had no idea that Khashoggi was the person who smuggled it out of Tora Prison.

“He kind of pops up everywhere, you know,” Rhodes says about Khashoggi on "Conspiracyland." “To me, this story kind of captures just how much this guy was not just a journalist in Saudi, not just an opposition figure in Saudi — he was a real regional figure who was connected to everybody, particularly people that were in the different movements against authoritarian leaders. And so there's a kind of a Zelig quality to his role over the last decade.”

It’s a Zelig quality that resurfaced just a few years later, when Khashoggi found himself in the middle of pro-democracy Arab Spring protests that swept through the region. Rhodes recounts on "Conspiracyland" how the Obama administration was deeply divided over those protests. Secretary of State Hillary Clinton, Secretary of Defense Bob Gates and even Vice President Joe Biden were wary of the demonstrations, fearing they would disrupt relationships with autocratic regimes like that of Egypt’s Mubarak, which the United States had long viewed as allies in the global war on terror.

Anti-government protesters react after a speech by Egyptian President Hosni Mubarak in Tahrir Square February 10, 2011 in Cairo, Egypt.  (Chris Hondros/Getty Images)
Antigovernment protesters in Cairo's Tahrir Square react after a speech by Egyptian President Hosni Mubarak, Feb. 10, 2011. (Chris Hondros/Getty Images)

“Mubarak has been an ally of ours,” Biden said in an interview with "PBS NewsHour" at the time. “I would not refer to him as a dictator.’

But Khashoggi immersed himself in the protests, flying to Cairo, huddling with Nour to plot strategy and celebrating the massive demonstrations in Tahrir Square against Mubarak. Khashoggi, like millions of others in the region, saw them as the harbinger of a new era in the Middle East. “We are witnessing the events of the massive transformation in Egypt” and a new “road map” for the region, he wrote for the Saudi newspaper Al Watan on Feb. 13, 2011 — and then tweeted out the article, proclaiming how proud he was to have written it.

The elation of Khashoggi and other pro-democracy activists was short-lived. Mubarak stepped down — an electric moment in Cairo — and was soon replaced by a democratically elected government dominated by the Muslim Brotherhood and headed by Mohammed Morsi. But Morsi failed to deliver on his promises of democratic reform and in 2013 was deposed in a coup engineered by the defense minister and former chief of military intelligence, Abdel-Fattah el-Sissi, and heavily backed — with funding and other support — by the Saudi government.

Supporters of Egypt's ousted President Mohammed Morsi chant slogans against Egyptian Defense Minister Gen. Abdel-Fattah el-Sissi at Nasr City, where protesters have installed a camp and hold daily rallies, in Cairo on July 28, 2013. (Hassan Ammar/AP)
Supporters of Egypt's ousted President Mohammed Morsi chant slogans against Defense Minister Abdel-Fattah el-Sissi in Cairo on July 28, 2013. (Hassan Ammar/AP)

The overthrow of Morsi was a crushing blow for Khashoggi. And for his efforts, he was subjected to a wave of vicious tweets and threats on Twitter.

I hope, inshallah, I see you get killed at Tahrir Square,” read one. And read another: “Can you just die and relieve people from your dirty face and your tweets that are dirty like your face?”

It was a sign of what would become one of the crueler ironies of the Arab Spring. The same social media tools the protesters used to spread their message of democratic reform would soon be turned against them — with Jamal Khashoggi as one of the prime targets.

Egyptian opposition politican Ayman Nour (L), flanked by Nobel Peace Prize laureate Yemeni Tawakkol Karman (R), speaks during a press conference as they hold pictures of missing journalist Jamal Khashoggi during a demonstration in front of the Saudi Arabian consulate on October 8, 2018 in Istanbul. (Ozan Kose/AFP via Getty Images)
Nour, with Nobel Peace Prize laureate Tawakkol Karman (right), in front of the Saudi Consulate in Istanbul on Oct. 8, 2018. They hold pictures of Jamal Khashoggi, then missing. (Ozan Kose/AFP via Getty Images)

Next on “Conspiracyland”: Episode 5, “The Rise of the Bullet Guy”

A new king, Salman, inherits the throne in Saudi Arabia and names his young son Mohammed bin Salman, or MBS, as his defense minister. U.S. officials — including President Obama’s ambassador in Riyadh — embrace him as a change agent who has the potential to bring his country into the 21st century. But others in Washington begin to have their doubts when MBS launches a barbaric war in Yemen that slaughters innocent civilians by the thousands.

In case you missed it:

Episode 1: “Exclusive: Saudi assassins picked up illicit drugs in Cairo to kill Khashoggi”

Episode 2: “Arms, harems and a Trump-owned yacht: How a Khashoggi family member helped mold the U.S.-Saudi relationship”

Episode 3: “‘I just fell apart crying heartbreak to you’: A murdered journalist's years-long relationship with Osama bin Laden”

Cover thumbnail photo illustration: Yahoo News; photos: Johnny Green/PA via Getty Images, Chris Hondros/Getty Images

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