This is the seventh year I’ve been playing in my high school fantasy baseball league. It’s one of the best and worst decisions of my life, and it’s the best because it’s the worst, and it’s the worst because it’s the best, and hopefully I’ve confused you all enough that you’ll all keep on reading. (“Lost” lasted for six seasons, didn’t it?)

I like to think of myself as a Moneyball player — a guy with an established system, which is probably the problem. Every year, I have the same strategy: draft as many power hitters as I can, punt batting average, take advantage of my league’s bizarre hatred of relief pitchers and pick up any player that has a great strikeout-to-walk ratio. Aside from my obsession with closers, it’s very Moneyball, at least in the most basic, stereotypical sense of the term. Also very Moneyball: I almost always make the playoffs, but I’ve never actually won.

So yes, fantasy baseball vexes me because I lose. Losing always hurts. But as my more fortunate friends will tell you it drives you nuts even if you win. Why?

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It’s only partly the losing: Sometimes I even get irritated when I do win, if things didn’t go according to plan. Seven years into The League, they rarely, if ever, do. Every year, I draft for power, and every year I end up near the top of the league in steals. Every year I draft for strikeouts and I end up in the cellar for those. The only thing that ever reliably goes to plan is my horrible, brain-meltingly bad batting average. I’m pretty good at fantasy baseball, but even though I can play the probabilities right, the game always reminds me that it’s fundamentally out of my control.

That’s the rub, as Shakespeare would say. [EDIT: …yes, I realized I botched the quote.] Fantasy baseball turns us into control freaks. In his book “Moneyball,” which turned advanced baseball stats into a popular phenomenon, Michael Lewis described Oakland Athletics general manager Billy Beane in fascinating detail. The nature of control freakery is that the more you expose yourself to the day-to-day volatility of the task at hand, the more you lose objectivity and the less control you actually have. As Lewis so elegantly put it, an obsession with control is “an exquisite torture: you must desperately need to see what you cannot bear to see.”

Unlike Beane, I don’t get paid millions of dollars to run a baseball team. My job is not on the line; my family’s pride is not at stake; the newspapers will not be posting my team’s successes or failures on the front pages for the world to see. But while I’m not a control freak and I don’t have any real pressure, I feel largely the same way about my own self-described master plans.

Deviations get to you, in the same way that writers get irritated when people compliment them for insights they didn’t actually intend to make. We have a systemic and perhaps inborn inability to fit our reactions to their actual significance: When a fly buzzes around, we can’t help but fixate on it, even though flies are rarely dangerous. We’re constantly “fooled by randomness,” which makes the games we play both compelling and frustrating in equal measure. Fantasy baseball is interesting because it is frustrating.

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The most engrossing games of all tend to resemble golf: difficult, out of your control but ultimately harmless. People who make fun of golfers that always get angry and bang their heads against the metaphorical wall are missing the point: Golf is supposed to be chaotic and hard. So is fantasy baseball. Both involve skills that are directly related to success, so you have a personal investment in success, but still involve enough randomness that nothing can be taken for granted.

These games are balances of control and chaos. A gust of wind might send your ball flying into the lake; your ball might take a bad bounce and roll into the bunker; Manny Ramirez might get suspended the day after you trade for him (this actually happened in our league once); Brandon McCarthy might get Tommy John surgery. It’s fun because you think you can will yourself to victory. It’s interesting because you typically don’t. You don’t have fun playing tic-tac-toe, do you? That’s because there’s no chaos or drama to it.

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We’re not just fascinated/irritated by deviations: we can’t help but create our own. There is no such thing as perfect faith in the system, even though the system restrains our worst excesses. In fantasy baseball, we find our fixations, players we just can’t avoid. Sometimes they’re just flights of fancy, like Drew Stubbs’ absurd potential. Sometimes they fit The System so well that you can’t help but draft them year after year. We fall in love with Brandon McCarthy’s mind-blowing strikeout-walk ratio and his Twitter account. We hope this is the year Aaron Hill hits 35 homers again. We draft Ryan Braun so often that we start naming our fantasy team “Biogenesis.” We grit our teeth and deal with the losing – and that’s OK, as long as we never become resigned to it.

The obvious question would be to ask whether I care about my players being good more than I care about winning. The answer would be no. The wins are never irrelevant. The trophy is always the goal. I am not willfully irrational when it comes to fantasy baseball. But it’s often very easy to imagine that the players we fall in love with will be the ones to carry us to victory. Maybe Desmond Jennings will put up a 20-40 season. Maybe Brandon McCarthy won’t get injured in bizarre, random and completely unforeseen ways. The McCarthy thing won’t happen this year because he’s out for the season. But the system is clicking, the last time I checked I was first in the league, and for now, I’m going to gloat.

Winston Shi’s English major editor is very unhappy that he misquoted one of Hamlet’s most famous soliloquies in the fifth paragraph. Find out the real quote at wshi94 ‘at’ stanford.edu