The Natural

He was not born in the woods to be scared by an owl.
—Epigraph, Shadow Box, 1977

From its first issue, in 1954, SPORTS ILLUSTRATED kept careful record of its freelance writing assignments on four-by-nine-inch index cards noting subject, deadline and fee. The most extraordinary stack of these cards belongs to George Plimpton, who died last week at the age of 76, leaving a hole in numerous lives and a deep legacy at the magazine.

Plimpton began contributing to SI in 1956 with a four-part series on the patrician Harold S. Vanderbilt and the America's Cup. That was three years after George cofounded and began editing The Paris Review, the literary magazine that was his spiritual hideout for 50 years, even as his singular and eclectic career as a man of both letters and sport played out in the pages of SI.

In the fall of '58, with something quite unusual on his mind, Plimpton visited SI's first managing editor, Sid James, and shared what James recognized as "a great idea." A group of major league baseball players were staging an unofficial postseason all-star game at Yankee Stadium in a few weeks, and Plimpton thought he could write an interesting article on what it was like to participate—pitching to, say, Willie Mays and Mickey Mantle. At a pregame exhibition he would face all the starters on both the National and the American League squads. The problem was, how could it be arranged?

In those days the most influential man in sports was arguably Toots Shor, whose restaurant was only a few blocks from the SI offices. James led an expedition there and bought drinks as he and Plimpton explained the idea to the man himself. Shor said the solution was simple: Offer $1,000 to the winning team. By evening came word that Plimpton's pitching exhibition was on. Whereupon Shor pulled him aside with a question: "You gonna box too?"

George smiled. The saloonkeeper understood that Plimpton was building on the work of one of his sportswriting heroes, Paul Gallico, who had spent a round in the ring with heavyweight champion Jack Dempsey back in 1922. But what Plimpton had in mind was more complicated than just looking for "the feel," as Gallico had put it. George wanted to share the secrets that were kept at the highest level of athletic competition—the ones he believed you could get to only in a huddle or a conference on the mound.

On game day at Yankee Stadium the public-address announcer bungled Plimpton's name, calling him George Prufrock, an irony not lost on T.S. Eliot scholar Plimpton. It was agreed that George would be a facsimile batting practice pitcher and that the hitters could wait for their perfect pitch. George got Mays to pop up, but many of the hitters were making him throw a dozen or so pitches—Ernie Banks let 22 go by—and after nine National Leaguers had batted, George called timeout. He could no longer lift his arm.

The resulting SI story was turned into the book Out of My League. Ernest Hemingway wired George from the Mayo Clinic, where he was being treated for depression, that it was "beautifully observed and incredibly conceived [with] the chilling quality of a true nightmare...the dark side of the moon of Walter Mitty."

Thus began George's amateur forays into professional sports for SI: Going three rounds and having his nose slightly "collapsed" by light heavyweight champion Archie Moore at Stillman's Gym in 1959; going to training camp with the Detroit Lions in 1963. (His SI account became both a book and a movie, Paper Lion, about "a 36-year-old free-agent quarterback out of Harvard.")

In reviewing these and numerous other works that followed, approving critics continued to draw on the Walter Mitty analogy, which had a surface truth, but overlooked the fact that in Mitty's daydreams he always succeeded, while in George's real-life adventures he always failed. But this truth—that his work had more to do with Everyman than Mitty—was always obscured by George's sophisticated but self-deprecating prose, which made him so easy and often hilarious to read. Likewise, far from being wholly un-suited for the sports he dove into, George was a graceful natural athlete who otherwise would never have succeeded in his failures, so to speak. He was a strong tennis player and could throw any ball he ever picked up: "It was the first instrument of superiority I found myself owning," he once said.