Thomas Friedman is not only an award-wining journalist, he is also – in Jerusalem – something of a local boy made good. So it was no surprise on Thursday night that Jerusalem’s Mishkenot Sha’ananim Auditorium was packed to the rafters for a Jerusalem Press Club chat with the star New York Times columnist.

Friedman, a three-time Pulitzer-prize winner and former NYT Jerusalem bureau chief, was relaxed and chatty with Director General of the Jerusalem Press Club Uri Dromi. He told the assembled crowd, made up largely of local journalists, that he owes a lot to Israel; his first-ever published story was covering a 1967 speech by Ariel Sharon at the University of Minnesota for his hometown paper in St. Louis Park, near Minneapolis. He also spent a number of summers in high school connecting with his Jewish heritage while living on Kibbutz HaHotrim, in the north.

Friedman, who has been busy this week while visiting Israel, attending the Institute for National Security Studies in Tel Aviv and spilling the beans on a potential framework agreement between Israeli and Palestinian peace negotiators, was on hand to discuss the role of climate change and technology in the Arab Spring. But the longtime Middle Eastern scholar also used his time at Mishkenot Sha’ananim to trace his journey through the region, from his undergraduate semesters abroad in both Jerusalem and Cairo to his posting for the NYT in Beirut, where he arrived less than two months before Israel’s 1982 invasion.

Friedman’s biography is well-known, and his 90 minutes of affable chatter contained no spoilers for loyal readers of his column. What the talk did offer, however, were a few choice morsels of journalistic advice – heady fare for a room packed with stringers and local correspondents, all of whom would likely kill for the kind of fame and following Friedman has amassed in his three decades at the NYT.

Recalling his first-ever published Op-Ed, for which he was paid $50, Friedman said, “I thought that was the coolest thing in the world. I was walking down the street, had an opinion, and someone paid me $50. I was hooked.”

A handful of years later, Friedman was serving as the New York Times’ Beirut Bureau Chief, and while filing the massive story of the US withdrawal from the city, the Telex system – which journalists used, pre-Internet, to file stories across borders – went down. With communications completely blacked out, The New York Times ran an AP story instead of Friedman’s text, and he missed out on seeing one of the biggest stories of his career making it to print.

“Your really just have to love the story for the story,” Friedman said of that crushing lesson.

Another key piece of advice?

“Whenever you see elephants flying, shut up and take notes,” Friedman said, recounting his time in Tahrir Square in the innocent days of January 2011, back when the Arab Spring was in its earliest buds. Calling that revolution “my most exhilarating journalism experience,” Friedman admitted that he has about 50 rules of thumb when it comes to reporting in the region, most of which are too politically incorrect to make it into print.

Asked by Dromi about his support for the 2003 US invasion of Iraq, which Friedman has made no secret of, he made it clear that he got behind George W. Bush at the time because he believes in democracy. And as to what the final verdict will be on the revolutions that have swept and upended the Arab world, Friedman told Dromi it was far too soon to tell.

“What we’re dealing with here are the implications of the end of the Ottoman Empire,” he said, adding that one way to understand the tectonic shifts across the Middle East was to realize that an entire region of people were shifting from a vertical rule, where they were governed from above, to a horizontal rule.

Likening Egyptian revolutionaries to tigers who had just been let out of a tiny cage for the very first time, he said that in order for democracy to flourish in the Middle East, it would require one of three things: a Mandela, a military (like Egypt), or a midwife (like the US in Iraq).

As the talk wrapped up, Dromi asked Friedman what he would say to Prime Minister Benjamin Netanyahu and Palestinian President Mahmoud Abbas, should he find himself alone with an elevator with either one of them.

With Netanyahu, Friedman said he would begin by acknowledging the immense security threats Israel faces, and then end by encouraging Netanyahu to be more flexible on the issue of the issue of the West Bank. “I’m not sure if it’s possible,” he said of a two-state solution between Israel and the Palestinians, “but if I were Israel and the Palestinians, I would do everything I could to test the proposition.”

As for Abbas, Friedman – who will meet him in person later this week – said he would advise the Palestinian leader to make Secretary of State John Kerry his best friend, because Kerry’s framework for peace in the region is the last best train he stands a chance of boarding.

Dromi, role-playing as Abbas, asked if Friedman was completely sure the Palestinians shouldn’t try to hold out for a better deal. Friedman shook his head no, adding, “It’s the last train. The next train is the one coming at you.”