For the better part of a decade, I resisted every invitation to play fantasy baseball. The older and busier I got, the less interested I became in the idea of devoting myself to assembling an imaginary ballclub and spending six months pretending to “manage” it by making phantom roster moves and make-believe trades. To me, this sort of behavior seemed, for lack of a better term, stupid.

It’s not that I’m a snob. Fantasy baseball’s nerdy reputation may be largely deserved, but the main reason I didn’t want to play is that the game seemed addictive. I’d had enough experience with “Rotisserie” players to know that the last place in the world you wanted to end up was trapped between two of them at a dinner party. Or for that matter, in an elevator, an airplane cabin, a checkout line, or (lord help you) the men’s room.

I like talking baseball as much as the next guy, but these people had gone so far beyond the bounds of normalcy that their conversations were impenetrable. If you didn’t have an educated opinion about how many bases Felipe Lopez might steal this season, you were left to stand there nodding like a dope. In my case, I had the added burden of being viewed as a potential source of inside information. “Hey, you’re a sportswriter…”

I’m not sure when my aversion to fantasy baseball broke, only that it was a gradual process. One factor was a pair of polls I saw that suggested as many as five million Americans played the game. More than this, the hobby seemed to be exerting some subtle pressure on the real game. Some of the ballplayers I interviewed for columns in The Wall Street Journal told me they heard critiques from their Rotisserie league “owners” almost as often, if not more often, than from regular fans.

In 2002, Mo Vaughn of the New York Mets told me that he was getting routine calls from some of his buddies back home who’d picked him for their fantasy teams and, like anyone else who’d conscripted Vaughn for that dreary season, had grown to wish they hadn’t.

Another catalyst was a case of professional burnout. Over the last few years, baseball had generated an abundance of news—none of it especially good. Rather than researching stories at the ballpark, most of my baseball “coverage” consisted of hunching over my desk talking to labor lawyers, agents, investment bankers, doping experts, orthopedic surgeons, insurance brokers, and disgruntled taxpayers. The high point was the day I broke the news that retired superstar Jose Canseco had used steroids during his playing career. I became so caked with baseball muck that I couldn’t watch a game without working myself into a lather about some tangential issue. Name a team, and I could tell you more than you’d ever want to know about the liquidity of its ownership group and a lot less than you’d expect about its pitching rotation.

It was then that I actually started to envy these fantasy nutjobs. If anything, they had the opposite problem. While I was consumed by steroids and ballpark financing, the punch they were drinking had intoxicated them to the point where they could dismiss, if not fully ignore, the game’s systemic problems. While I’d forgotten what it was like to watch a ballgame when you have an emotional investment in the outcome, these people had an emotional investment in the outcome of every pitch.

Beyond that, baseball was undergoing a transformation. Thanks to the creeping influence of the advanced statistical methods described in the bestseller Moneyball, many of the careworn tenets of the game were being upended. Suddenly there were people lurking around the front offices of baseball who believed (though they might not openly say it) that some scouts and managers and other old seers and mystics might be adequately replaced by laptops. I knew I was skeptical of this view, but I also knew that my knowledge of “sabermetrics,” as the discipline was called, wasn’t deep enough to validate this opinion. By playing Rotisserie baseball, I would have the perfect excuse to catch up with the latest currents of baseball thought. So the following November, I made arrangements to spend the 2004 season doing it full time.

While this would be my first attempt at fantasy baseball, I decided, nonetheless, to aim high. I applied for an invitation to Tout Wars, the nation’s top expert competition. There’s no prize money in Tout Wars, no trophy, and no celebratory banquet for the winner. To the people who compete in this contest, the payoff is the right to brag—not just about winning or finishing near the top, but just about being invited. To earn a spot in “Tout,” as it’s known to intimates, you have to have a foothold in the baseball information business—whether it’s running a fantasy sports advice site, publishing a book of projections, working for a statistics company, or writing a column for some prominent newspaper, magazine or fantasy sports organ. In other words, you need to be engaged in the business of “touting” ballplayers.

Among the contestants there were three lawyers, only one of whom is practicing. There’s an MBA, a Hollywood screenwriter, a pair of computer engineers, and a guy with a master’s in Victorian literature. Some of them held down day jobs while others, like Ron Shandler, made their living selling books and Internet subscriptions to other fantasy players. The talent level in Tout Wars was so high that five veterans of the competition had been tapped by real major-league teams to serve as scouts, statistical consultants or, in one case, special assistant to the general manager of the Toronto Blue Jays. Put simply, Tout was the closest thing fantasy baseball had to a national championship.

As foolhardy as it was for me to try to join this group as a novice, there was, apparently, nothing in its bylaws to prohibit me from trying. So after some discussion, I was invited to the upcoming draft in New York.

The plan was simple. While some of the Touts had contacts inside the majors, I was fairly certain none of them had a baseball Rolodex deeper than mine. So while they evaluated players by the numbers from their various cubicles, I would pick up the phone and talk to a scout or a general manager and get the real story. Further, I would use my access to clubhouses to try something that had never been attempted in fantasy sports: actively “managing” the ballplayers on my team.

If nothing else, I thought, Tout Wars would be fun and educational. It would also be a noble experiment, a chance to determine, once and for all, which device was better at predicting a ballplayer’s performance—the cold, hard numbers, or the human eye. If I could interpret all the intangibles the way these guys decoded numbers, I was sure I could do more than just tread water.

Fantasyland is the story of this attempt and, ultimately, a story about the state of baseball and the odd assortment of characters who orbit around it. But it’s also a tale about a guy who went from being a happily married sportswriter who wore a tie to work, to a caffeine-addled insomniac who spent tens of thousands of dollars, traveled nineteen-thousand miles, interrogated nearly two hundred major-leaguers, skipped three weddings, and ignored a fire raging in the building next door—all in the name of winning a Roto league with no prize.

Along the way I got to know many of the (real) players on my Tout Wars team, like David Ortiz, Doug Mientkiewicz and Jacque Jones. I had occasion to consult with dozens of baseball luminaries from Lou Piniella to Billy Beane. I took a crash course in baseball statistics from Sig Mejdal, a NASA biomathematician I hired as a team analyst. I got an education of another sort from my loyal assistant, Ferdinando Di Fino, a fantasy savant with an uncanny ability to remember obscure biographical details about ballplayers.  In lucid moments, I dug up the origins of fantasy baseball and discovered that the game dates back twenty years before the innovations of Dan Okrent and the well-known “Rotisserie League Baseball Association.” I also paid visits to my Tout Wars opponents, many of whom testify to the adage that eccentricity and genius are close relatives.

At times during this year, I found myself in situations that, if this book was a work of fiction, I would never have had the audacity to imagine. I learned more about baseball, and about baseball players, than I’d absorbed in thirty years of fandom. Most of all I met a lot of memorable people, had an enormous amount of fun and, at the end of the day, wondered why I’d spent so many years resisting this game.

(By the way, Felipe Lopez will steal twelve bases this season. You heard it here first.)

- Sam Walker