As an undergraduate reporter, Jeffrey R. Toobin ’82 rode in a limousine with writer Tom Wolfe and cursed with Yankees owner George Steinbrenner. But what he remembers most is the water. Lots of water.

Three feet of it, flooding Harvard Yard in the course of an evening. Maintenance crews chasing summer students, hoping they wouldn’t get electrocuted.

“It was a freak thing,” former Crimson President William E. McKibben ’82 says of the midsummer flood. A pipe had burst, and by the morning the water was gone.

Toobin—the New Yorker writer and CNN legal analyst—covers deeper waters today, but they were ones he never intended to swim.

GENETIC DESTINY

Jeffrey R. Toobin '82

As a sports writer and editorialist for The Crimson, Toobin wrote over 200 articles but never saw journalism in his future. “The Crimson was really very much a hobby,” he says. “The story of my career has been the story of coming into my genetic destiny.”

Toobin’s parents may have scared their son away from the profession.

His mother, Marlene Sanders, covered the Vietnam War and was a pioneering woman in television reporting. His father, Jerome Toobin, a producer for Bill Moyers, was at the vanguard of public broadcasting.

According to Toobin’s wife, his mother warned her son against going into journalism.

“Don’t touch it,” she said, “because success and failure are so randomly distributed.”

If true, the Toobins happened to be quite lucky. Emmys were so plentiful in their Upper West Side apartment, McKibben says, that television’s highest awards were used as doorstops (Toobin was able to add to the doorstop collection himself, earning an Emmy for his coverage of the Elián Gonzáles affair in 2000).

A literary couple, Sanders and Toobin pere were at home outside the spotlights as well.

Jerome Toobin kept what he called the “Book of Books,” recording the name of every book he read. When his father died following Toobin’s graduation from college, Toobin took the leather-bound volume and began to track his own reading.

From these bookish beginnings, Toobin arrived at The Crimson and was sent off to cover the crew team. Still fresh, he was forced to walk down to the end of the river to chronicle a sport he knew next to nothing about.

“It was kind of comical,” Toobin says.

One night that fall, he was handing in his story to the night editor, Amy B. McIntosh ’80.

“We didn’t fall in love that year,” McIntosh says, “but we definitely noticed each other. I credit the night editor’s desk as part of it.”

By the next year, Toobin and McIntosh were dating. Eight years later, they would be married.

“The Crimson spawned a great romance,” Susan D. Chira ’80, foreign editor for The New York Times and a former Crimson president, says.

“The joke was that he was the first man to sleep his way up the masthead,” McIntosh says. “Regularly women were accused of that, but in my board we were all women.”

Relationship aside, Toobin’s writing did not hurt his march up the masthead to sports chair and eventually editorial board chair.

The verve of the writer who will publish his fifth book this fall—”The Nine: Inside the Secret World of the Supreme Court”—shows early on.

“So for the 97th time,” Toobin began his preview to the 1980 Harvard-Yale Game, “the season begins and ends today. The Dartmouths and Browns and Princetons all stand as ancient and distinguished rivals, but there is only one Yale Game—The Game—and for about three hours on a late fall afternoon, it is the only Game in the world.”

‘DISCO TOOBIN’

For Toobin, though, The Crimson wasn’t the only game.

Christopher M. Jedrey, who now practices law at the Boston firm McDermott Will & Emery, advised Toobin on his thesis, a study of the late years of Samuel Adams.

“It was pretty clear that he was doing something interesting,” Jedrey says, “so I leaned on him as hard as I could.”

Toobin doesn’t remember needing much leaning on, reveling in his visits to the Massachusetts Historical Society across the river.

“I loved immersing myself in the colonial world,” Toobin says.

His introduction to Adams and his circle produced a fascination in the constitution and law.

McIntosh remembers taking a trip one New Year’s Eve with the man who she used to call “Disco Toobin” because he was one of the few who would show up at dances. They wandered all over Manhattan and stopped in front of the midtown offices of Debevoise & Plimpton, the white-shoe corporate law firm.

“I’m going to work there someday,” Toobin said. And so, three years later, he was off to Harvard Law School.

From there his path was anything but corporate, working for the U.S. attorney in Brooklyn and assisting Lawrence E. Walsh in the investigation of Oliver North and Iran-Contra.

McIntosh describes the Brooklyn job as the “real ‘Law & Order.’” Toobin spent his days prosecuting drug cases, tax cheats, even a pet cemetery scandal.

It was exhausting work, and after a falling out with Walsh following the publication of his first book about the Oliver North case, Toobin jumped at the chance to leave behind the practice of law.

TALK OF THE TOWN

“He was very frustrated with the job at the moment,” current New Yorker editor David Remnick says. It was 1993, and Tina Brown had recently become editor of the eminent weekly.

Remnick had just joined the magazine as a staff writer. He and Toobin met at a dive bar. Over a drink, Remnick suggested Toobin meet with Brown.

“I basically changed careers over a weekend,” Toobin says.

Talk of the Town, the storied house built by E.B. White and James Thurber, needed another layer of paint, and Brown wanted Toobin to add a newsier finish.

Remnick says that Toobin’s experience made him a natural hire.

“He was coming at this a little on the late side, but he had knowledge about an area of life. Jeff had been out in the world,” Remnick says.

“He wasn’t just a graduate of an unfortunate University in the suburbs of Boston,” Remnick—who was rejected from Harvard—says.

In 1995, a white Ford Bronco dragged across the nation’s television screens, and Toobin had his biggest story.

“O.J. Simpson killed those two people,” Toobin says, “and the rest of my career is history.”

Remnick says, “Somebody inside the O.J. defense team revealed to Jeff that they were going to use race. From there he was just off to the races”—Block that metaphor!, Mr. Remnick—“Oh, that’s a terrible pun. He just launched. He took off.”

With the scoop, the New Yorker’s newsstand sales shot up, and Toobin found himself wanted by every television network.

From the Simpson trial onward, Toobin’s reporting has scraped the bottom of celebrity crime, covering Michael Jackson and Martha Stewart, and hit the top of the legal profession as well, landing at the Supreme Court.

Jedrey, Toobin’s thesis advisor, remembers his student trying to explain the 2000 Bush v. Gore decision on national television.

“He was on camera with the decision in his hand, somewhere in Florida, sweat dripping down his face, on the run, explaining this big complicated, appalling decision. He did a great job,” Jedrey says.

“One of the things that I’ve always liked is the mix of high and low,” Toobin says.

It’s something he has done since those green Crimson days, dashing down the river to write about unknown oarsmen and dashing off an editorial about divestiture soon thereafter.

“He understands the world is serious and important,” McKibben, once a Talk of the Town writer himself, says, “while also understanding that there is no need for him to be serious and important.”

Today, the father of two bounces between the World Cup (“an editor-sanctioned boondoggle of the highest caliber,” Remnick says) and Google’s copyright court battles.

“His shrink,” McIntosh says, “sometimes says he can’t commit to anything.”

—Staff writer Samuel P. Jacobs can be reached at jacobs@fas.harvard.edu.