A quick conversation could go on for hours.
When we first met, he was an advisor to Prince Turki bin Faisal, Saudi Arabia's long-time intelligence chief.
The Kingdom was battling al Qaeda on its own streets. Huge shootouts with terror cells in the heart of the capital Riyadh were not uncommon and Khashoggi had the experience -- and connections -- that benefited the ruling family.
Khashoggi came from humble roots. Like many Saudis of his generation, he benefited from royal largesse with an overseas university education.
He went to Indiana State University, where he studied journalism. Upon his return to Saudi Arabia, he worked his way up through the ranks of reporters at a scattering of Saudi and regional newspapers.
Then, like so many reporters before him, he got a big break covering an overseas conflict.
It was the late 1980s. The Saudi intelligence service was working with the CIA and Pakistani counterparts to oust the Soviets from Kabul.
Jamal, in the words of a friend, became an activist. He developed close connections to many of the young Saudi men who were flooding to the fight, encouraged by their government and the CIA.
Among those he met and got to know well was Osama Bin Laden, whom he would later interview on several occasions.
His access to Bin Laden and others like him put Khashoggi on Prince Turki's radar, after which a close relationship developed.
Saudi authorities were hungry for information on what their young men were up to, and Khashoggi had the access to help fill the blanks for the government.
He was last known to have visited Bin Laden in the mid 1990s, when the terror leader was hiding out in Sudan. Khashoggi's goal was to convince him to give up terror and return to Saudi.
Back in the desert Kingdom, Kashoggi's journalism career was turbulent.
He was sometimes critical of Saudi Arabia's conservative clerics, and even his royal connections could not save him from being fired as editor of national newspaper Al Watan.
But Khashoggi understood that his homeland was not a homogeneous conservative enclave. There were princes and others in royal circles who supported his views and quietly provided space for a gentle challenge of the status quo.
He was the highest-profile reporter to publicly question Saudis -- calling on them to examine their role in the 9/11 attacks on the United States.
Yet despite being at times a thorn in the side of the establishment, when they needed his connections and expertise they still called on him for help.
Late 2002, as al Qaeda began to emerge in Riyadh and other cities around the Kingdom, Prince Turki brought him back as an advisor.
Prince Turki went on to become Ambassador to the UK and later to the US. Khashoggi would spend time in both countries helping his boss.
When Turki moved on from his ambassadorships, Khashoggi returned to journalism, continuing his abrasive relationship with the country's conservatives.
When Mohammad Bin Salman's father became king three years ago the young prince emerged as a force for change, removing conservative religious clerics and scrapping some of their strict rules.
At first, Khashoggi embraced MBS, as he is known, as the breath of fresh air he'd been long hoping for.
But as MBS consolidated his power -- ousting the crown prince so he'd be next in line to the throne before locking up royals for corruption and putting critics behind bars -- Khashoggi spoke up.
It was then that Khashoggi said he began to get threatening calls, telling CNN's Hala Gorani: "I received a phone call ordering me to go silent with no court decree, with just someone from the royal court, an official from the royal court who was close to the leadership and ordering me to be silent. That offended me."
He decided to leave the Kingdom, resting for a while in London, where friends described him being at a low ebb, unsure of what his future would be.
It wasn't long, however, before he decided to combat Bin Salman's leadership style.
He moved to the United States, applied for a green card and wrote for the Washington Post, despite his fears of what could happen to him.
Close friends knew he was worried -- they said he understood clearly what the cost of crossing MBS could mean.
Still, he walked into the Saudi Consulate in Istanbul Tuesday 2nd of October, despite friends fearing it could be a trap.
He hasn't been seen or heard from since. Turkish officials have hinted darkly that he was killed there; Saudi officials say he left minutes or an hour after arriving and have denied any involvement in his disappearance.
His friends are preparing for his funeral.
Dead or missing, Khashoggi is generating the type of headlines he has spent the past year of his life producing -- questioning Bin Salman's suitability for leadership of Saudi Arabia.
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