Jamal Khashoggi became known across the Middle East as a man with ties to the top of Saudi politics and at times as an unofficial spokesman for palaces of Riyadh. He was also one of the most connected journalists to Al Qaeda leader Osama bin Laden and one with ties to a web of various Muslim Brotherhood operatives and activists.
In the west, it was the connections to Riyadh, coupled with his often boundary-pushing journalism, that made his name.
With still no clarity surrounding the disappearance of the 59-year old Saudi journalist in Istanbul last week, friend, colleagues and acquaintances have expressed shock at the unfolding mystery. He was last seen at the Saudi consulate in Istanbul.
He made a name as a foreign correspondent with his coverage of anti-Soviet mujahideen in Afghanistan and the rise of Al Qaeda in Yemen and Sudan in the 1980s and 1990s.
Mr Khashoggi was born in the western Saudi city of Medina, revered in Islam as the burial place of the Prophet Mohammed. After a youth spent studying Islamic ideology, Mr Khashoggi became less conservative later in life and advocated for reform across the wider Middle East.
He is well-read and a member of intellectual circles in the kingdom after studying for his degree at Indiana State University in the US.
In 1988, Mr Khashoggi wrote one of the first profiles of rising radical Islamist militant Osama Bin Laden, a man he travelled with in Afghanistan and met several times for his stories.
Salameh Nematt, former bureau chief for Al Hayat in Washington, has known and worked with Jamal since early the 1990s. He describes him as “a decent man”, who didn’t fear expressing his opinions.
“He was the go-to person when it came to radical Islamic groups across the region as he always had impeccable sources”, Mr Nematt tells The National.
Peter Bergen, Al-Qaeda expert and author, told The Washington Post that in the days he was spending time profiling Osama Bin Laden, Mr Khashoggi was religious and at least deeply sympathetic to movements such as the Muslim Brotherhood. This, Mr Bergen says, allowed him to spend so much time with the elusive militant leader.
The links to Islamist hardliners he cultivated for his stories, however, would get him into trouble.
Mr Nematt remembers the first time they met in the Jordanian capital when Mr Khashoggi was travelling to cover the court trial of an Al Qaeda member.
“He was detained at the Amman airport and ordered to be deported back to Saudi Arabia because of his ‘suspicious’ links with leaders of Al Qaeda, as I was told at the time”, Mr Nematt recalls. “I used my connections in the government to have him released and allowed into the country.”
This trouble wasn’t just in moving around the region and he spoke openly about being periodically barred from writing his columns and or appearing on television.
“I would know [when he is in trouble] because he wouldn’t answer his phone”, Deb Amos, an award-winning journalist at NPR covering Saudi Arabia and the region, told The National.
Ms Amos said. “Eventually the storm would pass and he would answer again.” This time seems to be different.
Those around him agree he is committed to dialogue, arguing the Arab world has to engage with political Islam and never shying away from talking about regional and domestic issues. At the same time, his vocal support for the Muslim Brotherhood and political Islam raised questions about his liberal leanings. He had close contact with the Saudi royal family and became very well-tuned to the workings of the country’s hierarchy.
Even at his most critical, Mr Khashoggi didn’t call for an end to the Saudi monarchy or the leadership of the country. His criticism was largely levelled at the policy and practice of the government.
“[Politically] he agreed with the new Saudi reforms - but objected to the limits to dissent”, Ms Amos said.
Recalling her last conversation with Mr Khashoggi at Princeton University last year, she described her friend of 20 years as fearless and restless.
“Jamal was always courageous”, she says. What stood out was his “laser-like analysis of Saudi Arabia in a country that has no tradition of an open free media. He did it because he loved his country”, she said.
The prominent media man has had ties at the very top of Riyadh’s political and business circles but left for self-imposed exile in the US in 2017. There he wrote critical columns in The Washington Post against some of the kingdom’s policies.
Hisham Melhem, a prominent Arab journalist in Washington, was one of those who has known Mr Khashoggi for years in his different capacities - both a semi-official embassy spokesman in Washington, as a top political commentator on the inner workings of palace politics and later as a self-exiled writer.
“I met Jamal during his short stint as an advisor to Saudi Arabia’s ambassador in Washington, Turki bin Faisal Al Saud [in the late 2000s]”, Mr Melhem said. Then in interviews, “he articulated the official views of his government. He was friendly and affable and I was impressed with his knowledge of the American political system”, he tells The National.
Before Turki bin Faisal Al Saud’s posting to Washington DC, Mr Khashoggi had worked in Riyadh with the 22-year head of Saudi Intelligence before following him to the embassy in London and Washington. During this time, Mr Khashoggi had close ties to the intelligence bureau and some reports suggest he may have worked with it.
It was these links to the top officials in Saudi government that led the west to see Mr Khashoggi as the go-to analyst on the happenings in Riyadh. With the ear of top officials, but a flair for free thinking and outspoken writing, he was seen as the man to explain government policy but not be branded a mouthpiece.
Throughout this time, he held several top posts in Arab media outlets. He became editor-in-chief of Saudi-based Al Watan in 2003 before leaving the post after less than two months. He led the paper for a second time in 2007 and his tenure lasted for three years until he resigned in 2010.
Saudi businessman Prince Al Waleed Bin Talal appointed him to run Al Arab television station in Bahrain in 2015 with the aim of broadcasting no holds barred coverage of the Middle East from the Middle East, but the channel was shut down within hours of beginning.
That is where his career took on less direction and he started to “float” around, as one person who knows him described it. He began writing for The Washington Post in September 2017 after leaving Saudi Arabia and wrote around a dozen columns for the paper, mostly about the kingdom. His 1.6 million Twitter followers give his voice a wide reach.
Mr Melhem says Mr Khashoggi was different when he returned to Washington last year.
“He was more reserved and weary... he struck me as someone struggling to speak out on behalf of more openness and reform, but not to be seen as proposing radical change.”
Mr Khashoggi, insists Mr Melhem, “did not want to be seen as a ‘political dissident’, but simply as a critical voice for reforming the Saudi system politically and certainly not through violence.”
But Mr Melhem says he’s seen his friend’s gradual political transformation. “We saw him become fully committed to the worldview of the Muslim Brotherhood and found solace in the Turkey of the AKP... he was too Islamist for me, and I am sure I was too secularist for him” Mr Melhem, adding that he hoped the Saudi writer would return.
Randa Slim of the Middle East Institute says Mr Khashoggi’s writing had always been his priority.
“As he once put it in a conversation with friends about happiness, he was the most happy after submitting an article”, she recalled him saying.
Ms Slim added that he left Saudi Arabia because he was censored from writing but not because he felt at the time that there was a threat to his life.
His friends and long-time colleagues all said they hope he is alive and well but expressed shock and sadness at his disappearance and possible death.
“Jamal was – or, as we hope, is – a committed, courageous journalist,” the Post's editorial page editor Fred Hiatt said in a statement.
Leaving aside politics and getting to the bottom of his whereabouts, for Mr Khashoggi, his family and those who serve in his profession, must be the most important outcome of current investigations.