Alter says he planned to go to law school, but “forgot. Oh, and I never got around to taking the LSATs.”

After finishing his thesis comparing Henry Kissinger’s academic work and his performance in office and graduating summa cum laude in Social Studies, Whitaker took a prestigious Marshall scholarship to study at Oxford.

But like Alter, he found he was at loose-ends. He was unhappy doing graduate work, and eventually left Oxford without getting a degree.

“I found myself sneaking away from Oxford to do stringing for Newsweek constantly,” Whitaker remembers. “I think it took being away—really away, from my parents, from everything—for me to realize what I wanted to do was journalism.”

All that stringing paid off, and Whitaker was offered an entry-level job at Newsweek. He left Oxford and took a three-month trip around the world, taking up Pan-Am airlines on their “80 days around the world for 1,100 pounds” offer—which allowed him to fly for three months as long as he moved in one direction and only took Pan-Am flights.

When he arrived at Newsweek, Whitaker did not have a desk or an office.

“For six months, I moved from desk to desk, and finally when they gave me an office, it was windowless,” he says. “Nobody would have seen me at that point and thought I was being groomed for anything more than writing sidebars.”

Meanwhile, Alter tried his hand at journalism as well. He would join Whitaker and Contreras in a few years, after brief stints at The Washington Monthly and The New Republic.

“I wrote my way onto The Washington Monthly,” Alter remembers. “Out in the world they don’t care too much about your college work, but what they care about is what kind of clips you have in professional journalism. If you want to be a writer, you have to write; you have to sell your wares like an entrepreneur.”

Whitaker’s wife Gelber remembers hearing about Alter when he was working at Washington Monthly.

“Jon was one of the first people that Mark told me about,” she says, “as this brilliant writer at the Washington Monthly, who was making nothing and eating spaghetti day in and day out.”

Alter soon followed in the footsteps of his college buddies when the editor of the Washington Monthly, Charlie Peters, convinced Bill Broyles, the newly appointed editor of Newsweek, to hire Alter as his assistant and informal “spy.” His role was to help ease the transition and tell Broyles, an outsider of Newsweek, what was going on internally.

“So many of the people that I now have good working relationships with despised me at first,” Alter says with a chuckle.

“He seemed like too nice a guy to be a spy,” Gerber says. “Eventually, he won everyone’s respect at the magazine. Jon has this incredible combination of being incredibly knowledgeable about the most arcane details about American politics and also being an incredibly nice guy.”

Alter’s days of espionage may be over now, but he still serves a special role as a “minister without portfolio,” as he describes it, who informally advises in various capacity on the magazine, in addition to his senior editor and columnist duties.