Daniel Okrent can’t pinpoint the exact moment when he realized his dream of becoming a major league baseball player like his hometown heroes on the Detroit Tigers — perennial All-Star Harvey Kuenn in particular — was never going to happen.
However, it might have been during one of the countless games he played near his family’s summer place at Cooley Lake. Or maybe it was in the early spring or late fall, in the middle of Wisconsin Avenue, near the intersection of Six Mile and Wyoming on the city’s northwest side.
That’s the neighborhood where Okrent grew up and lived until he graduated from high school, and where he and his buddies dodged traffic as they swatted at pitches and tracked down pop-flies. At some point reality sank in and Okrent figured if he couldn’t play the game he loved, at least he could write about it.
“I mean baseball was how I started as a writer, because it was something that I knew a lot about and cared about a lot,” says Okrent, who discovered his love for writing as the sports editor of the school paper at Post Junior High and Cass Technical High School.
“I started getting on what was called the Second Avenue bus, picking it up on Six Mile and taking it seven or eight miles downtown to high school every day,” he recalls. “Cass Tech was less than half a mile from Briggs Stadium (later Tiger Stadium, before Comerica Park) and the school day ended for us around 2 or 2:30 p.m.
“We could walk over to the stadium and get there in the sixth or seventh inning, and it really wasn’t much to sneak in. The (stadium) was pretty much open and we’d go sit in the bleachers and watch the rest of the game and then take a bus home.”
Okrent pauses here, seeming to savor a particularly fond memory from so long ago, then adds, “I felt like I owned the city.”
Soon after he enrolled at the University of Michigan in Ann Arbor in the fall of 1965, Okrent joined the staff of the college newspaper while pursuing a major in American studies.
“It was a combination of literature, history, and art history, but I really was an extremely mediocre student, I barely graduated, and I didn’t pay any attention to my studies,” he admits. “So I say I majored in working on The Michigan Daily. That’s where the excitement and action was, and that’s also where my passion was.”
By the time Okrent graduated from U-M in 1969, he already had a job lined up in New York City. “I went to work at Alfred A. Knopf as a book editor, then at Viking Press,” he says. “My last job in publishing was when I was made editor-in-chief of Harcourt Brace when I was 28. I was not qualified and I wasn’t ready for it. I failed at it and I was fired 15 months into it, and it was the best thing that ever happened to me. I wasn’t made for that world.”
There was a silver lining to the career setback: The burning passion Okrent had for baseball, set aside during college, never really went away. “That’s when I started writing about baseball,” he says. “I think my first piece in Sports Illustrated was in 1980. I wrote for them fairly frequently, and then in Esquire quite a lot.”
Okrent wasn’t only writing about the game he loved, he was constantly thinking about it — which inspired a long-simmering idea for a way baseball fans could enhance their experience with the game by actually competing against each other. Legend has it that Okrent put the final touches on his concept while on a fabled flight one early winter evening in 1979 from Massachusetts to Texas.
“Hartford to Austin,” he says drolly. “That’s the foundational myth and it’s basically true.”
The premise he pitched to a cadre of fellow New York-based hot stove devotees was simple enough: Participants build on-paper teams with real ballplayers, producing dream lineups only their wildest imaginations would allow, then act as managers or owners as they buy, sell, and trade players whose performances and statistics in real games determine the success of each off-field, on-paper team.
“We would have lunch every month or six weeks, and that’s where I first presented the rules and we codified it,” he says.
It turned out to be a luncheon summit of historical proportions: Not only were the rules and regulations of Okrent’s idea finalized, but because it all took place at Manhattan’s now defunct La Rotisserie Francaise restaurant, Rotisserie League Baseball was officially memorialized and hatched.
“Our first season was 1980, and most of us in the league were in the media so we got a lot of media coverage,” Okrent says. “The following year, during the 1981 strike, sportswriters started writing about it when they didn’t have any real baseball to write about.”
Okrent’s experience with Rotisserie, coupled with his array of work as a freelance baseball writer, seemed to be the perfect opportunity for him to parlay his love for the game into a career covering it full-time. But that notion had no appeal.
“I continued to write about baseball occasionally until roughly 1988, but I realized I had made the mistake of turning a hobby into a job,” he admits. “I could no longer see the game the way a fan saw it. I also knew too much — this player was a racist, that one beat his wife, etc. I wanted to know less, and go back to being a fan.”
In short order, he pivoted onto another path. “In 1984 I founded a magazine called New England Monthly,” he says. “Not related to the current magazine with the same name. It won two national magazine awards in its first two years of existence, which is kind of unheard of.”
Okrent served as editor for five years. After the magazine folded, he became editor of Life magazine for another five years. It was during this stint that he appeared in Ken Burns’ Baseball documentary, described by one pundit as “the romantic in the red sweater.”
“I think I was on camera more than anybody else, and years later I could tell when it was being replayed on PBS because people would look at me on the subway,” he recalls. “Thirty years had passed, I’d gained 30 or 40 pounds, and they were trying to figure out who the hell I was.”
Okrent followed his time at Life with a corporate job at Time Inc., leaving in 2001 when he took early retirement at 53 and began writing books. “Great Fortune,” a history of New York City’s Rockefeller Center, was not only critically acclaimed but a finalist for the Pulitzer Prize. More book deals clearly loomed, but then Okrent got a call from The New York Times.
“That led to my being hired as the first public editor,” he says. “It was for a term-certain 18 months. I announced in my first column, which was in December of 2003, that my last column would be in May of 2005, and I had 18 incredibly thrilling, intense, sleep-disrupting, nerve-unraveling months. It was both the most interesting job I’ve ever had and by far the most difficult because every day I was just dealing with people who were unhappy.
“I would go to the editors or the writers on the paper (to check on a potential correction) and they’d say, ‘Who the hell are you? What are you doing here? Get out of my face!’ It was like being in internal affairs in the police department.”
Okrent got another book out of his gig at the Times; “Public Editor No. 1” is a compilation of his columns in the paper. He’s since published “Last Call,” a deep dive into the history of prohibition, and just last year delivered “The Guarded Gate,” a sobering look at the story of immigration in the early 20th century. “I’m always working on a book, and I’m right now between books and looking around for a new one,” he says.
I’m always working on a book, and I’m right now between books and looking around for a new one. — Daniel Okrent
Meantime, as if it was really necessary for Okrent to further demonstrate his range, interests, and ability to write well about virtually any topic, he and a business partner bought the rights to the website OldJewsTellingJokes.com, and in 2012 turned it into a smash show. “It ran for 520 performances off-Broadway, and has played since then in 13 other cities,” he says.
And here’s where the Okrent narrative takes yet another unexpected turn: The unabashed Mel Brooks fan and successful producer of a show heralding the Brooksian brand of irreverent ethnic humor is the same guy who in 2009 wrote a cover story for Time magazine entitled “The Tragedy of Detroit.”
“I went back and spent time there and wrote about what I found and how awful it was, and explained why I thought it had become that way,” Okrent says. “It was a very controversial piece. People in Detroit were furious about it for a variety of reasons, but that was really Detroit at its absolute nadir. It was on its way to bankruptcy and things were just awful.”
In the decade since, Okrent, who splits his time between homes in New York City and Cape Cod, has made regular visits to his hometown and is encouraged by the progress, but guarded when it comes to discussing the city’s future.
“Certainly the direction has been positive and the change is possible, particularly downtown,” he says. “When it’s going to reach the neighborhoods fully, I don’t know. I think the real enduring calamity of Detroit is the school system. Until it can be resolved and straightened out, the city will never have a full comeback.”
But Okrent is quick to emphasize it was that very same public school system that made an indelible impression on his life.
“In my case, the great formative Detroit experience and, in fact, the great educational experience of my life was Cass Tech. Here I went from my own rather insular neighborhood to a high school that was probably about 25 percent or 30 percent African-American. That’s when I learned about the variety of Detroit — all ethnic groups and income levels.
“I could sit in the class between the son of a Wayne State professor and the daughter of a banker, and behind the son and daughter of auto workers. It was a totally democratic and meritocratic place, and I cherish it. My years at Cass Tech had more impact on me, I would say, than any other three years of my life.”
That experience, and all Okrent gleaned from it those many years ago, undoubtedly explains why he had a specific request toward the end of our interview: “I would just ask you to please make certain (to say) in the piece that I think Detroit was a wonderful place to grow up in the ’50s and ’60s if you were white. There’s no question that I, and others of similar background, experienced the city in ways that were not so readily available to so many Black families.”
It’s been over 50 years since Dan Okrent left Detroit. And the decisions he’s made during a rewarding and wide-ranging career suggest he relies on his gut instincts and never dwells too much on second-guessing anything.
“I’ve often thought about moving back to Detroit,” he says wistfully. “For at least the last 10 years, maybe a little bit longer. My affection for the city, my care, my concern for it is really boundless. But it’s not gonna happen. I’m 72 years old …”
Okrent trails off here, and after a few seconds he continues, more energized. “I remember saying to myself, If the Tigers called and said, We’d like you to be the general manager, would you move back to Detroit?”
And now he reaches back all the way to those long-ago summer days at Cooley Lake, and connects solidly with the first true and everlasting love of his life. “I said, Geez. If the Tigers called me and asked me if I wanted to be the batboy, I’d move back to Detroit.”