For those views, reported in The Washington Post and articulated in tweets and at a Washington think tank, he was ordered by the Saudi authorities to stop writing and speaking publicly, unleashing a chain of events that may have culminated in his disappearance and possible death inside Saudi Arabia’s Consulate in Istanbul last week.

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By the summer of 2017, Khashoggi had concluded that if he was to continue pursuing his lifelong work as a journalist, he had no choice but to leave Saudi Arabia. He relocated to Washington, where he became an increasingly outspoken critic of Saudi Crown Prince Mohammed bin Salman, gaining prominence for his views through a regular column in The Post.

There are now fears that his opinions could have cost him his life, or at least his freedom. The Turkish government, according to two people familiar with the investigation, has concluded that Khashoggi was killed shortly after entering the Saudi consulate in Istanbul on Tuesday to secure a document he needed to marry his fiancee in Turkey.

Saudi Arabia has denied any involvement, saying Khashoggi left the consulate that afternoon.

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As the days pass without news of his whereabouts or well-being, concerns are growing that a man who has courted controversy throughout his life may have fallen victim to Saudi Arabia’s most controversial attempt yet to silence a critic.

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Khashoggi, a cousin of the late billionaire arms dealer Adnan Khashoggi, can’t be counted as a true dissident, friends and colleagues say. They note that he has not opposed the monarchy, called for regime change or even urged the replacement of Mohammed, the architect of Saudi Arabia’s attempt to introduce greater social and economic reforms, as well as its harsh crackdown on political freedoms.

But any one of his columns for The Post critiquing Mohammed’s methods could have made Khashoggi a target of the royal family’s wrath, at a time when Saudi women who welcomed the prince’s reforms have been imprisoned for daring to ask for further changes.

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In September 2017, he described his despair at the growing oppression in Saudi Arabia but also his support for Mohammed’s attempts to modernize the conservative kingdom.

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“My friends and I living abroad feel helpless. We want our country to thrive and to see the 2030 vision realized,” he wrote, referring to Mohammed’s economic program. “We are not opposed to our government and care deeply about Saudi Arabia. It is the only home we know or want.”

His columns — some of which, including this one, were translated by The Post into Arabic — served to increase his visibility and also, it is likely, the fury of the Saudi royal family, said Hisham Melhem, a Washington-based colleague of Khashoggi’s who used to host a political talk show on the Saudi-owned Al Arabiya network.

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“He is prominent because of the platform The Washington Post provides him,” he said. “Other critics don’t have this kind of platform, and they were very angry with him in Saudi Arabia.”

Fred Hiatt, editorial page editor of The Post, said Khashoggi knew he was taking a risk by criticizing the Saudi government, even though he was abroad.

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“But he felt an obligation to speak out when so many of his countrymen were being jailed or muzzled. As an experienced, highly knowledgeable journalist with a point of view, he was a natural fit to our roster of Global Opinion columnists, and we have been proud to publish his work,” Hiatt said.

Even while denying Saudi involvement in his disappearance, Saudi government supporters on Twitter have sought to denigrate Khashoggi not as a government critic but a supporter of the Muslim Brotherhood, an Islamist movement once tolerated but now outlawed in Saudi Arabia as a terrorist organization.

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The charge dates back to the earliest days of his career, when he was a reporter covering the war in Afghanistan in the 1980s and 1990s, including the rise of then-little-known Osama bin Laden.

Khashoggi was embedded with bin Laden’s circle of associates, traveled extensively with the al-Qaeda leader in Afghanistan and wrote one of the first profiles of him for a Saudi magazine in 1988, after being personally invited by bin Laden to accompany him into Afghanistan, according to Peter Bergen, author of the book “The Osama bin Laden I Know.”

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Salameh Nematt, a Jordanian journalist based in the United States who was Khashoggi’s colleague and editor at the Al-Hayat newspaper at the time and has remained a lifelong friend, recalled frequently being called upon to rescue Khashoggi from run-ins with authorities because of suspicions about his ties to his extremists. On one occasion in the early 2000s, Nematt had to persuade Jordanian airport authorities not to deport Khashoggi after suspecting him of links to al-Qaeda.

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“He was getting into trouble all the time because of his connections with al-Qaeda groups, but he was doing that as a journalist,” Nematt said. “He was very well linked, to the point where some people suspected he was financing extremist groups. I personally was convinced he was doing his job as a journalist and covering both sides.”

At no point did Khashoggi express support for extremist groups, Nematt said. Rather, he took the view that “you have to deal with the moderate Islamists as a political reality or you will have to deal with the extremists. The failure to deal with the mainstream Islamists will lead to the extreme zealots taking over,” he said.

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“You could say he wrote, not justifying the actions of the Islamists or extremists, but saying these people had feelings of grievances, of oppression, are the product of violent regimes and clampdowns.”

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Bergen, now an al-Qaeda expert with the New America think tank, interviewed Khashoggi extensively about his experiences with bin Laden and concluded that Khashoggi was at least deeply sympathetic to moderate Islamist movements such as the Muslim Brotherhood. But later in his life, he moved toward a more liberal, secular point of view, Bergen said.

“At the time, according to Jamal himself, he was religious. He would have spent quite a considerable amount of time with bin Laden. There was no other way to do the reporting. He was almost certainly a member of the Muslim Brotherhood,” he said.

However, over time, Bergen said, Khashoggi “became increasingly secularized, and his critiques of the Saudi regime come from a more liberal perspective. He went from being someone who by his own account was quite religious to a liberal critic.”

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By 1999, he had ended his travels and became a prominent journalist in Saudi Arabia, often courting controversy but always managing to remain within establishment circles. He was twice fired as editor of the Saudi Arabian daily Al Watan, and an attempt in 2015 to launch a TV network, Al-Arab, was shut down within days for reasons that were never publicly explained.

In the 2000s, he was close to Prince Turki bin-Faisal, a former head of Saudi intelligence. During Turki’s tenure as ambassador to London and then Washington, between 2003 and 2006, Khashoggi served as Turki’s adviser and became the de facto spokesman for the Saudi Embassy, said Melhem, who hosted him several times on his talk show as a representative of the Saudi government.

Meanwhile, many members of the international news media came to see Khashoggi as a reliable commentator on Saudi affairs, an insider who could be counted on to give insights into the thinking of the opaque monarchy but who was outspoken enough not to be considered a mouthpiece. And he always responded to calls.

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“He was so close to the royal family and decision-makers, he was almost an unofficial spokesman for quite a while,” said Hussein Ibish, a scholar at the Arab Gulf States Institute in Washington who knew Khashoggi. “And then he was estranged.”

During a meeting in Washington last December, Khashoggi spoke of the immense personal price he had paid for his decision to go into exile to continue speaking out. His wife had filed for divorce, many members of his family had shunned him, and he had lost his home and possessions.

When he walked into the Saudi Consulate in Istanbul last week, he was in the process of rebuilding his life. He had met and become engaged to Hatice Cengiz, and he was seeking a document, required under Turkish law, confirming that he is not legally married elsewhere. They planned to marry soon, friends say.

In the absence of conclusive evidence as to his whereabouts, it is impossible to know what has happened to him, said Nematt. But he fears that Khashoggi’s visit to the consulate may have presented the Saudi authorities with an opportunity to silence his voice.

“Jamal’s criticism was too dangerous for them because it undermined the Saudis’ relationship with the U.S.,” he said. “Perhaps the Saudis thought this was an opportune time to silence him, whether he was kidnapped or killed.”

In his column a year ago, Khashoggi described his determination to continue speaking out. “To do otherwise would betray those who languish in prison,” he wrote. “I can speak when so many cannot.”