Inside Baseball


May 22, 2025

Nantucket Book Festival author Christian Sheppard discusses his new book, The Ancient Wisdom of Baseball.

Written by Brian Bushard
Photography by Beowulf Sheehan


It was another let-down season for the Chicago Cubs when Christian Sheppard’s daughter was born. It was the late ’90s, and Sheppard found himself watching the last-place team in the National League Central from the hospital maternity ward, whispering the play-by-play to his newborn daughter as his wife rested. Around that time, another voice caught his attention. A fellow graduate student at the University of Chicago’s Divinity School asked him how he would raise his daughter. It was a question not just about religion, but a philosophical inquiry about the very ideals he would impart on his daughter. Without hesitation, Sheppard quipped, “I’m going to raise her a Cubs fan.”


In the two-decades since his daughter’s birth, Sheppard—who was raised Catholic and as a Red Sox fan—has asked that question over and over again. Somewhere along the way, he realized baseball, by its very nature, carries a sort of philosophical wisdom similar to religion and mythology. Its stories of legends are not unlike the heroes of Greek mythology. Wrigley Field is Sheppard’s church. His seat is his pew.


“What would it mean to ask of baseball the questions we usually put to philosophy, and the questions that we usually put to religion, which is basically to say, what is this world I find myself in, and how should I live there?” said Sheppard, who recently released his first book, The Ancient Wisdom of Baseball. Sheppard, a professor of liberal arts at the School of the Art Institute of Chicago, will discuss that book at the Nantucket Book Festival this June

I was not completely coincidental that Sheppard happened upon the Homeric epics. Sheppard holds a Ph.D in religion and literature from The University of Chicago. He has written about art, food, culture and sports for The New York Times and The Chicago Tribune, and for10 years, he taught The Odyssey at The University of Chicago. The heroes in the Homeric epics embody virtues of courage and bravery. Their successes were triumphant. Their failures were tragic. That’s not dissimilar from Sheppard’s childhood hero, Boston Red Sox catcher Carlton Fisk.


When Fisk’s home run in Game Six of the 1975 World Series struck the left field foul pole at Fenway Park—an iconic image for Sox fans despite the World Series loss—Sheppard remembers cheering for Fisk, as the catcher waved his arms in hopes his bending fly ball would stay fair. When Fisk was traded to the Chicago White Sox six years later, Sheppard called it an “unforgivable sin” to a teenage Red Sox fan like himself. “The formulation I came up with in the book is that every baseball game is the ritual reenactment of this essential myth,” Sheppard said.


The game proceeds slower than other professional sports, allowing for conversation. There's also an interesting relationship between location, history and family that plays out over years of watching baseball, Sheppard said. There’s even a term for it: psychogeography. It’s the idea that because places like Fenway Park and Wrigley Field are still around, spectators can associate those ballparks with pivotal moments in baseball, even associating those events with older generations that witnessed them. When you go to Fenway, you’re at the same field where Babe Ruth once pitched and where Ted Williams hit the longest home run in the park’s 110-plus year history. A formative memory for Sheppard was when his grandfather told him he saw Babe Ruth play at Fenway Park. As a child, Sheppard remembers seeing Carl Yastrzemski’s 3,000th hit from his seat at Fenway in 1979. He was also there for a Rico Petrocelli home run that went up into the lights—a heroic act for a kid at the ballpark, and the kind of stuff out of Robert Redford’s The Natural.


“So when you go to Wrigley, you can recall that that's where Babe Ruth called his shot,” Sheppard said. “When we see a home run at Fenway, we think that's where Big Papi in the clutch helps break the curse [in 2004]. Baseball has this resonance that goes over the generations that relates individuals to America, in some ways at its happiest.


That resonance extends to younger generations, as well. Looking back at his life as a Red Sox and Cubs fan—and as a father—Sheppard said watching baseball has become a richer experience. “When you share baseball with your own kids, it's like you get the joy of seeing them see a home run for the first time,” he said. “There’s away in which having a family, having someone to share it with, amplifies it for yourself in ways that you couldn't imagine.

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