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Founding editor of the website Deadspin, Will Leitch helped pioneer the postmodern world of sportswriting – all the news that’s fit to print, plus all the stuff that maybe isn’t.

By Jamie Malanowski / Photos by David Friedman

Less than two hours after shooing his parents out of the residence hall parking lot, Will Leitch ’97 MEDIA, already aware that he wanted to become a professional writer, moseyed into the offices of The Daily Illini and volunteered to work on the newspaper. Asked what his interests were, the University of Illinois freshman mentioned movies and sports, and the next day he was assigned to write an article about an intramural basketball game and to review a film. That was in 1993. Now, not 20 years later, Leitch, 36, is one of the most popular, widely read, in-demand sportswriters in the country and a film reviewer for Gawker.com. Insightful, witty and gifted with a breezy writing style, he is a mainstay at New York magazine and a valued contributor to GQ, The New York Times and other publications. Tempting as it may be to draw a straight line from the callow applicant of yesteryear to the polished professional of today, taking the shortest distance between two points seldom tells the most interesting story – or the most accurate. As with so many young writers, Leitch’s success did not come automatically, but after struggle. In his case, attaining a place in the mainstream media first meant becoming one of the breakout stars of the ragingly popular sports website Deadspin, where, as possibly the world’s first great postmodern sportswriter, he became a figure of adulation, scorn and controversy. As detours go, it was splendid.

“I had a pretty typical experience – YEAH!” says Leitch (pronounced “leech”), who is not cheerleading his own lines, but a layup by the Illini men’s basketball team, whose games he has religiously observed since his ladhood in Mattoon, a small town that lies approximately 48 miles on a straight drop south of the University. We are watching the game in the Downtown Bar & Grill in Brooklyn, not far from the leafy, brownstone-lined street where Leitch makes his home with his wife, Alexa, an interior decorator. (“She’s a fan of the Georgia Bulldogs, but in her wedding vows, she pledged to root for the St. Louis Cardinals. I didn’t force her to, but I’m holding her to it.”) Over several samples of local brews, Leitch, interrupting himself to cheer, moan and text his father who is at the game (“He got a seat behind the bench, although how I don’t know. We Leitches are upper-deck folks”), shares his version of the time-honored tale in which an aspiring neophyte invests several years of hard work before achieving overnight success.

Like many a hero of this kind of tale, Leitch made his way to New York City and for several years scuffled out a living, bumping from job to job, collecting enough clips to remain confident in his talent without ever quite managing to plant a second foot on the ladder of success, or for that matter, firmly securing one on the bottom rung. At one point, he spent a year answering phones in a doctor’s office, while continuing to write. “Quitting wasn’t an option for me,” says Leitch. “I knew if I left New York that it would be over for me.” After this phase of the experience, which usually culls the herd of the untalented and uncommitted, he emerged with more confidence, more connections and a good idea.

In 2003, along with several other young writers, Leitch started a site called The Black Table. He contributed a column called Life As A Loser, most famous for a first installment in which he tells the tale of being dumped by his fiancée hours before appearing as a contestant on the television game show “Win Ben Stein’s Money,” a comic predicament which Jimmy Kimmel, then Stein’s announcer, learned about and gleefully proceeded to bat about like a beach ball. (A sad tale, sure, but as any writer will tell you, love comes and goes, but a good, humiliating, faithless fiancée story is a joy forever.) “That experience was a turning point,” says Leitch. “I stopped thinking that I needed to get a job at an established place. I began to realize that if I wrote good stuff, people would find it.”

Read more: http://www.uiaa.org/illinois/news/blog/index.asp?id=437

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