Ambition, Academia, and Athletics

HUDSON VALLEY TALENT | People are talking about . . . Robin Lester

Robin Lester is not one for stereotypes. Through the years, the longtime academician and award-winning author has continually worked to disprove false generalizations that linger within society.


Let’s start with the misconception that rural, small town midwesterners go nowhere. Lester, now 78, spent his formative years in Nebraska, where the educational resources were lackluster. “I’m one of those lucky unlucky people who grew up in a small prairie ranch community where the schooling was not very good,” he jokes. Not the type to let roadblocks get in his way, Lester took the self-taught approach. He learned physics from a textbook, studied Greek in his spare time, and became a skilled writer without ever receiving constructive criticism or edits from his teachers. His hard work paid off when he won a regional essay contest as a high school senior.

A Man of Letters

“In defense of my old high school, we did have superb interscholastic athletics,” he says. Lester became a ten sport letterman, mastering everything from track and field and basketball to football. His athleticism and dedication aided him at the University of St. Andrews in Scotland, where he completed his undergraduate degree in history and earned a prestigious athletic blue award while serving as captain of the school’s basketball team.

Lester did not come anywhere near the “dumb jock” stereotype, instead proving himself to be both a top notch player and a dedicated scholar. “All of the athletes on the team were serious students,” he recalls. After St. Andrews, Lester went on to pursue a master’s degree at Pepperdine University, followed by a Ph.D. in history from the University of Chicago. It was at Chicago that he dove headfirst into the research that would become a lifelong interest. He chose to complete his dissertation on the culture of American intercollegiate football. It was a project that served as the basis for his acclaimed book, Stagg’s University: The Rise, Decline, and Fall of Big-Time Football at Chicago (1999), featuring the famous, early twentieth-century football coach Amos Alonzo Stagg, credited with inventing the tackling dummy, the huddle, and the reverse and influencing generations of American school sports coaches.

Diverse Teacher

In addition to becoming a nationally recognized author, Lester made a name for himself as a capable instructor. Early in his career, he taught at suburban public schools and at the University of Chicago and Columbia College in Chicago before eventually accepting a position in 1975 as headmaster at Trinity School, the prestigious independent school for Ivy-bound students in New York City.

“I really enjoyed teaching kids who were well motivated,” he says. Although Lester personally attended public school during his youth, he came to love the academic principles ingrained in the private school system. At the same time, however, he recognized that there was more to do. In 1978, he helped to found Prep For Prep, an intensive 14-month program that extends across all five boroughs and prepares young students of color to enter competitive independent schools.

“The parents, as well as the kids, had to sign a contract to commit to the program,” Lester explains. The rigor of the program matched with its proven results – many students qualified to attend Trinity – earned the school recognition by New York Magazine for “Best Prep School in Town” in 1985. Notably, Prep For Prep aimed to be as inclusive as possible so as to provide a wealth of opportunity to bright young scholars. The program continues today. Lester notes that, thanks to that initiative, children living on Park Avenue and others living in the Bronx were then and are still able to share a classroom at Trinity.

Lifeong Writer

Although Lester enjoyed his time and accomplishments as headmaster, he and his wife, Helen, the renowned children’s book author of more than 40 books, with whom he has co-written several short tales, needed an escape from their 24/7 life at Trinity.

“Trinity School’s headmaster lives in the building,” he explains. “We were pretty much wedded to the school like a Siamese twin.” He and Helen bought what Lester calls “a shack in the woods,” in Pawling as their weekend retreat. They kept the home as they moved to San Francisco, Chicago, and Minneapolis before eventually returning to upstate New York in 1998.

“We think Pawling is about the nicest community there is,” he enthuses. Throughout the years, he has been an active member of the Pawling community, serving as a board member of the Holiday Hills YMCA Conference Center, the Pawling Historical Society, the Pawling Garden Club, the Pawling Community Foundation, the Pawling Teen Center Advisory Board, and Mizzentop Day School.

Even with a full extracurricular plate, Lester always prioritizes writing. Although he used to wake up at 4:00 a.m. to squeeze in a few golden hours at the computer before heading off to teach classes in Manhattan, he now wakes up at 6:00 a.m. daily to work on his compositions. While the schedule is strict, it has undoubtedly paid off. Lester’s works include dozens of articles, essays, and book reviews, as well as Born Red, a coming-of-age prarie novel, and Princes of New York, a novel about a New York City school. Most recently, he completed a private memoir for his family’s enjoyment.

Currently, he and Helen are hard at work on their latest project.

“My wife and I have been asked by the University of Chicago for our papers,” he reveals. Once complete, the archives will include the couple’s children’s books along with Lester’s novels and drafts.

“We are busily putting them together,” he says. With an end of December deadline, he and Helen have their work cut out for them.

Not that Lester is complaining, of course. This Nebraska boy is proof that hard work can go a long, long way.

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