How to Fail Better in Baseball and Life with Mark Kingwell

Mark Kingwell is a Professor of Philosophy at the University of Toronto and a contributing editor of Harper’s Magazine. His most recent books are Fail Better: Why Baseball Matters (2018), Wish I Were Here: Boredom and the Interface (2019) and On Risk (2020). Forthcoming is The Ethics of Architecture (2021). In this interview, we discuss what it means to fail better on the baseball field and what that sport can teach us about the rest of life.

Mark Kingwell by Anthony Jenkins
Mark Kingwell (art by Anthony Jenkins)

Greg: What led you to write Fail Better, a philosophical book about baseball?

Mark: Well, I’m a lifetime fan of the game and, as my professional path has turned out, I’m an academic philosopher by profession. The two may be related. I have always loved thoughtful writing about baseball—Kahn, Angell, Updike, Giamatti—and appreciated its cerebral qualities. I likewise cherish the many fictional treatments: Kinsella, Malamud, Greenberg, Harbach, Hall.

So I guess I wanted to make a very small contribution to the vast literature on the game. Emphasis on very: maybe something like a decently executed sacrifice bunt. I also thought there were lessons from philosophers, Kant and Aristotle among others, that hadn’t yet been folded into the discourse about the game.

Greg: What makes baseball uniquely suited to this project compared to other sports?

Mark: The obvious answer is that it is linear rather than territorial, unbound by any clock, and distantly pursued. Objectively, it is a rather strange game. You are part of a team out in the field, but you are also alone, waiting for things to happen. The battery is working every pitch, to a batter who is likewise alone and waiting for the deal. Everyone is thinking hard. It is meanwhile a game of angles and movement, with sudden explosions of action out of apparent stasis, and thus a much more beautiful game than soccer, though I love that too.

Finally, the margins are astonishingly narrow. Having the distance between bases set at ninety feet is apparently arbitrary but in practice deeply meaningful—the difference between out and safe on a grounder from a speedy hitter. Like many fans, I’ve visited the street intersection in Hoboken, New Jersey, where the diamond is set out on the four corners. This might or might not be the original site of baseball, but its mythic significance is deep. Not incidentally, this place in pre-urban Hoboken was once known as the Elysian Fields, like the Champs-Élysées in Paris. In Greek mythology, this is the place where the heroic and immortal dead end up. Awesome.

Greg: Was there a point in your life where you began to realize that certain aspects of baseball transcended the sport?

Mark: Not sure about that. Baseball is inextricable from life, or anyway from mine, as I try to show in Fail Better. This has been true for me since I was very young, watching the World Series on television with my father, scoring the games and learning how to bat and catch with a hand-me-down first-baseman’s trapper from my brother Steve (I still have it).

But a key moment was probably when I read Bart Giamatti’s Take Time for Paradise, which came out in 1989. I was still in graduate school at Yale at the time, and I saw Professor Giamatti at a social event. He looked very ill and died not long after. The Pete Rose betting scandal was in the air. It all shook me up a little. Baseball is a pastime, but it is also politics, economics, culture, technology, poetry and history.

Greg: What can baseball teach us about failure and how to fail better?

Fail Better by Mark Kingwell

Mark: The cliché is that a batter who fails seven times out of ten is a potential Hall-of-Famer, and the one who fails just six times is a god. Baseball is designed to break your heart, as Giamatti said, both for fans and players. Failure is its dark core. I think often about that scene in Bull Durham (1988) where Crash Davis (Kevin Costner) dilates on the difference between making it to The Show and living out your career in the minors: a few lucky bounces, a seeing-eye grounder, a slightly sluggish shortstop. It’s that minute. A perfect game can end up as a loss, as I discuss concerning Harvey Haddix.

But the game goes on. That’s what I chose that phrase from Samuel Beckett as my title and epigraph. “Fail better” means that you acknowledge error, take responsibility, keep trying and hope to do better the next time around. I note that all books are likely failures, because no book can say everything perfectly. I thought it was ironic that a few baseball fans, who should know better, scolded me for some factual errors in my book. Of course there were, because there is not a book in existence without them! The good thing about books, in contrast to score sheets, is that I was able to correct the errors in subsequent print runs of Fail Better. Baseball fielders can’t do that: their Es stay on the record forever.

Greg: What other lessons can baseball provide?

Mark: (a) There is no justice in life. (b) Practice does not make perfect. (c) Skill is essential to success but insufficient for it. (d) Don’t think too much out there. (e) It’s always nice to come home. (f) Always hit the cut-off man. (g) A pop-up behind third base is the shortstop’s play.

Greg: How close does real-life organized baseball come to the idealized version? In what ways does it fall short?

Mark: The usual things compromise ideals: big salaries, corporate greed, raking fan money with overpriced beer and hot dogs.

I do think the COVID-19-shortened season of 2020 showed fans something important, namely that the game can transcend economic factors and just be wonderful. It was almost—almost—like going to a minor-league or even semi-pro game and seeing players and fans there simply for the love of the game.

In a recent essay written after her death in 2019, I talked about my mother’s love of baseball. Her affection was pure and almost religious. She just adored being there to watch the opposing nines. It was not theoretical or literary, and maybe not even competitive. That’s when baseball is ideal.

“Fail better” means that you acknowledge error, take responsibility, keep trying and hope to do better the next time around.

Greg: Do modern changes in baseball (analytics, the erosion of some unwritten rules, declining and aging viewership, rule changes, etc.) alter the significance of baseball?

Mark: We saw in the 2020 playoffs how analytics failed when matched against intuition, passion, luck and circumstance. You can’t game the game, not entirely anyway. I personally like the intellectual aspect of statistics, but there is always an uncontrollable margin, as there is in all statistical analysis.

I have no strong views on rule changes. Like the famous stages of drunkenness has it, sometimes I’m for the designated hitter and sometimes against (not from drinking, for the record!). Lowering the pitcher’s mound was clearly good for the game, for example. But I think automatic walks are bad, because they remove contingency, and I’m old-school enough to dislike the runner-on-second rule in extra innings. Play it out, I say. The slippery slope would put us into mercy-rule territory. Come on: there’s a difference between Little League and The Bigs.

Conventions, though, depend on developing culture. I love extravagant bat flips, in part because I’m a Blue Jays fan and Jose Bautista did one of the best ever. It would of course be cool if some otherwise flamboyant player just cranked a no-doubt homer and then celebrated by simply laying the bat reverentially on the ground. I would admire that kind of cool.

Aging viewership is a hard call. There are some science-fiction worlds—Star Trek, for example—where baseball has simply disappeared into the maw of history. I hope that doesn’t happen. My students definitely prefer basketball and NFL football to baseball. But when I was still able to go to games in person I was always struck by the youth and diversity of the crowd. In a weird way, it’s nice for me to feel old at a baseball game!

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