When I meet Weingarten for lunch at the Tastee Diner in Silver Spring, he shows up wearing a Bronx High School of Science hoodie. Weingarten graduated from that highly touted magnet school in 1968. He’s one of a half dozen Pulitzer winners who spent their teenage years roaming its halls. He’s not, for the record, one of the seven Nobel laureates. Weingarten describes Bronx Science, as it’s known, in this semi-fond manner: “The school was entirely filled with Jews wearing eyeglasses as thick as Sealy Posturepedic mattresses.”
He then enrolled a half hour south at New York University. He majored in psychology, but he preferred the newsroom to the classroom.
“It is possible to spend 80 hours a week editing a paper, which is what I did,” he says.
Three credits shy of that psychology degree, he abandoned higher education to hang out with Puerto Rican street gangs in the South Bronx. He freelanced a piece about the gangs to New York magazine, which put it on the cover. The story is strong and gutsy, but reading it now is like listening to Bob Dylan’s first album—enjoyable enough, but he doesn’t sound like himself yet.
With one doozie of a clip in hand, Weingarten next got a job reporting for the Albany Knickerbocker News, where he wrote about city-hall corruption for four years. In 1977, he went to Lansing to cover state government for the Detroit Free Press. Then his career took a strange turn: He accepted an editing job at the National Law Journal in New York. Why leave a daily paper to be an editor at a publication for lawyers? Because he wanted to be closer to his then girlfriend—or, in Weingarten’s words, so he could have sex on a regular basis. He ended up marrying that girlfriend, whom he refers to as “The Rib” in his columns so she can keep her identity private. They have two kids, Molly and Dan.
But that wasn’t the only reason for the switch from reporter to editor. “I felt like I was never going to be a great writer,” he says. “I felt like I was going to be a good writer at best. I wanted to be great at something.”
In 1981, he became associate editor at Tropic, the Miami Herald’s Sunday magazine. The magazine had earned a writerly reputation, but when Weingarten took over as the top editor a few years later, he worried that readers were ignoring Tropic and he wanted to “snap their heads back.” According to David Von Drehle, then a staff writer at the Herald, Tropic became “the most ambitious newspaper magazine going.”
Von Drehle recalls Weingarten chewing ballpoint pens, paper clips, and whatever other office supplies he could gnaw into submission. “I remember him going over stories again and again,” he says. “It was scary and inspiring and instructive to fall under his spell as a young journalist because it opened your eyes to what it takes to be good.”
One of those young journalists was Marc Fisher. “He’s superficially messy,” says Fisher, a former Metro columnist who’s now a senior editor at the Post. “He’s at once frivolous and fun and on the other hand deeply serious about doing top-quality work and meaningful work with every at-bat.”
Tropic’s content mirrored its editor’s dual personality. It could be doleful one week and spit-take irreverent the next.
In September 1989, Weingarten and company published a cover story about the new Orlando Magic basketball team in which they mocked the city of Orlando and referred to its team’s general manager as a weenie. The article was written by Dave Barry, whom Weingarten had hired in 1984, thereby launching the career of perhaps the most famous humor columnist of the late 20th century. The article’s stated purpose was to “whip up a mindless hatred on the part of our readership in hopes of creating a classic sports rivalry.” Below a photograph of Magic cheerleaders, rather than printing their actual names, Weingarten made up monikers like Flunky, Poobles, and Spaz.
What may be most memorable about the issue is the cover photo. Pictured is Barry spinning a basketball on his middle finger. The cover line extends “heartfelt best wishes” to Orlando on the arrival of its new team.
Weingarten somehow convinced the then executive editor of the Herald that flipping the bird “isn’t really offensive to people.” Turns out it really is offensive to people, and the paper got letters, lots of letters, including one from a mother who asked what she should tell her son when he asked why his hero, the great Dave Barry, was making an obscene gesture on the cover of a magazine. The executive editor later said running the photo was the only decision she ever regretted.
Another up-and-coming writer on that staff was Joel Achenbach, who later also made the leap to the Post. One day in Miami, Achenbach turned to Weingarten and said, “We will never have better jobs than this.” More than two decades later, Weingarten says he can’t disagree.
But Weingarten then quit that dream gig over a staple. The Herald management told him it was planning to stop stapling the magazine and start printing it on lesser-quality paper. Weingarten said if they did that he would resign. When management made good on its threat, Weingarten made good on his. “I had to leave or I had no credibility for the rest of my life,” he says, “at least in my own mind.”
So in 1990 he wrote to the Washington Post and asked for a job. Mary Hadar, then the assistant managing editor for Style, got the letter. She knew Tropic because her parents lived in Fort Lauderdale and she read it when she visited. And she was a fan of the magazine—enough of one to tell Weingarten that if the Post didn’t hire him, she would jump out a window to create a slot.
The Post hired Weingarten.
Next: Witty and neurotic on page and in person