“The Trading Desk” (31 Longreads in 31 Days, Day 28)

Michael Lewis is a prolific nonfiction writer, author of The Big Short, Liar’s Poker, Moneyball, The Blind Side, as well as hundreds of articles for The New Republic, Vanity Fair, and The New York Times.

The Trading Desk, which appeared in the March 30, 2003 edition of the New York Times Magazine, was adapted from his book Moneyball, which would later be made into a movie starring Brad Pitt. But even if you never read the book or saw the film, this 8900-word feature article would stand on its own. It’s a great story about the changing business of baseball, Oakland A’s general manager Billy Beane, and the players who get moved around like playing pieces on a board.

Billy Beane

Photograph by Michael Zagaris/Getty Images

At the heart of the story is the way Beane defied conventional wisdom about how to evaluate baseball players and build teams. With limited money to spend and fewer star players to use as assets for trades, Lewis shows Beane to be gutsy and resourceful, relying on mathematics, data, and personal charm to do what he can’t with a large payroll.

Here, he frames the larger context for all the action in the story:

For more than a decade, the people who run professional baseball have argued that the game was ceasing to be an athletic competition and becoming a financial one. The gap between rich and poor teams in baseball is far greater than in football and basketball, and widening rapidly. In the middle of the 2002 season, the richest team, the New York Yankees, had a payroll of $133.4 million, while two of the poorest teams, the Oakland A’s and the Tampa Bay Devil Rays, had payrolls of less than a third of that. A decade before, the highest-payroll team, the New York Mets, spent about $44 million on players, and the lowest-payroll team, the Cleveland Indians, a bit more than $8 million. The growing raw disparities meant that only the rich teams could afford the best players. A poor team could afford only the maimed and the inept, and was almost certain to fail. Or so argued the people who ran baseball.

But when you actually look at what happened over the past few years, you have to wonder. The bottom of each division has been littered with teams — the Rangers, the Orioles, the Dodgers, the Mets — that have spent huge sums and failed spectacularly. On the other end of the spectrum is Oakland. For the past four years, working with one of the lowest payrolls in the game, the Oakland A’s have won as many regular-season games as any other team except the Atlanta Braves. They’ve been to the playoffs three years in a row and twice taken the richest team in baseball, the Yankees, to within a few outs of elimination. How on earth did they do it? As early as 2000, Commissioner Bud Selig took to calling the Oakland A’s’ success “an aberration,” but that was less an explanation than an excuse not to grapple with the questions: how did they do it? What was their secret?

The story goes about the business of answering that question, using the example of one trade to reveal the thinking and strategy behind Beane’s maneuvers.

Lewis paints the big picture well, but he also zooms in to let us see Beane in action, wheeling and dealing:

He has two hours to find someone who will take Venafro off his hands. The Mets are a good idea. Beane picks up the phone and dials the number for Steve Phillips, the general manager of the Mets. A secretary answers.

“Denise,” Beane says, “Billy Beane, vice president and general manager of the Oakland Athletics. Denise, who is the best-looking G.M. in the game?” Pause. “Exactly right, Denise. Is Steve there?”

Steve isn’t there, but someone named Jimmy is. “Jimmy,” Beane says. “Hey, how you doin’? Got a question for you. You guys looking for a left-handed reliever?”

He raises his fist again. Yes! He tells Jimmy about Venafro. “I can make it real quick for you,” he says.

How quick?

“Fifteen minutes?”


“I can give you names in 15 minutes,” Beane says. “Yeah, look, I’d do this if I were you. And I’m not [expletive] you here Jimmy. I’m being honest with you.”

Lewis’ work is great because he does two things very well: he’s a fine explainer, and he writes great scenes. He helps make sense of complex worlds of finance, professional sports, and business, but he doesn’t get buried jargon and acronyms. He doesn’t forget that ultimately, these stories are about people, and takes the time to give the reader a sense of who they are. He delivers a story about a big picture, but pays attention to the details of the people inside the frame.

Read The Trading Desk →

New media Sports Guy rises as old media sinks

Bill Simmons, the 'Sports Guy'A few weeks ago, New York Times did an interesting profile of one of my favorite writers, Bill Simmons, better known as ESPN’s “Sports Guy.”

It includes some interest background on the early days and his rise to becoming a model of a new breed of columnist that broke a lot of the conventional rules of the news business:

At the time, Mr. Simmons was 28, making $50 a week as a contributor to America Online’s Digital City Boston, he recalled in a recent interview. “My goal was to make the welcome screen,” he said.

Barely a decade later, he has proved that prediction true: He is the Sports Guy on ESPN.com, where his column has an estimated 1.4 million page views a month; his weekly podcasts have been downloaded 21 million times this year via iTunes; and his new book, at 700-plus pages, “The Book of Basketball,” reached No. 1 on The New York Times nonfiction best-seller list last week.

That Mr. Simmons is perhaps America’s most famous sports columnist, with a salary said to put him among a tiny elite of sports commentators, is a tribute to his undeniable work ethic and fascination with his subjects: sports, popular culture, lists, himself, basketball, his friends and family, and his readers.

Perhaps most interesting was how his early struggles to make a career as a writer pushed him to the web:

“I tried to break in conventionally — but it didn’t matter how good you were, you had to wait 10 to 12 years to get a column,” he said in an interview. He wrote for a while and even spent a year bartending before giving the Internet a shot. “The Web site was a way to get out all the frustration of not having a column.”

Over the years, the Internet has prevailed over print — in July he stopped writing his column in ESPN’s magazine. “I got bored with the space of it,” he said, “of having to write 1,200 words, and with a deadline six days in advance. It is impossible to write a great sports column six days in advance.”

Simmons’ approach and style reflect his roots on the web. His stories are punchy, timely, light, and filled with pop culture references and hyperlinks. When he wants to, he writes long: his columns can run anywhere from eight to 20 pages, depending on his whim. He devotes columns to “mailbag” question and answers from readers. His podcast (“The B.S Report”) rivals his column for popularity. He tweets a lot.

But it’s not just a matter of using the right tools and and media. It’s also clear that Simmons has a passion and love for his work. I think this makes a difference. When you read his column or listen to his show, it’s evident that he’s having fun.

Simmons uses the full range of modern media to build a community of readers and listeners. He’s a good example of a modern approach to journalism and writing that breaks many of the established “rules.” He shows that the newspaper business may be shrinking, but the market for good, smart writing remains strong.

Check out the rest of the NY Times profile here.

Theme: Esquire by Matthew Buchanan.