Is thinking with your head overrated?

I must make a confession regarding the column you are about to read. If this column was a car, I’d be selling it as “salvaged.” See, it was in an accident earlier this week. I initially wrote my column on Monday evening, but did so without visiting THT that day. After I got home from work and attending an opening of a new bar in Manhattan on Tuesday, I came home figuring I’d read over my piece, make a few tweaks and submit it. Well, while I was not looking at the road, my column crashed into Jonathan Sher’s. I had written a quick column to make sure all the readers were aware of the Yahoo innings cap loophole. Tuesday evening I discovered that Jonathan had done that already. So, what follows is a bit of residual discussion about that issue, and my own exploration of a potentially imminent gut check.

I may try to pull this extra innings strategy off in my highest stakes league. I’m currently sitting in third place, 3.5 points out of the lead. I’m trailing the team ahead of me in strikeouts by 12 and could make up two more points with three wins. The problem is that I don’t know how much room I’ll have in the rate stats and the fourth place owner is right on my heels. If I try to go for broke and the move explodes in my face, I could knock myself out of the money altogether.

The other dynamic that will make things interesting is that the fourth-place owner is the most aggressive owner in the league, and he has less to lose than I do. So, I know he’ll make things interesting by taking advantage of this loophole – I know he knows about it because he’s done it before. …And, he’s the guy ahead of me in Ks, so I’m not sure I can even take that point if he goes all out on this strategy too.

I can’t be sure how many others in the league may be going for this. The fifth and sixth place owners are close enough that a late run could give either or both of them legitimate shots at usurping the final money slot.

Right now, I’m thinking that my strategy might be to beat my opponents to the punch and shoot my load on the second to last day of the season, so that I get my pick of the free-agent pitchers and leave the rest of the teams to fight it out on the last day. Doing that would mean that I’d go over my innings a day early, and thus sacrifice a day’s worth of potential closer production. I do have an outside shot at making up another point in saves, so I’ll see where I stand in a few days.

I’m hoping to avoid being stuck in a gut-check situation, where I’d have to decide whether to risk the smaller prize for a chance at the jackpot. I like to think that if I felt I had a decent chance at making it big, I’d put it on the line. At the same, I like to think that I’d have enough discretion to make a decision that is within the bounds of reasonably prudent risk assessment, which basically means that if there were a blinking neon sign advertising l95 percent odds against my profiting from the gamble, I’d abstain.

If I were a true quant, I could really model this. If my league pays out at 6.67 times entry fee for first place, 3.67 times for second, and 1.67 times for third, what probabilities for each outcome would have to exist to dictate that I don’t risk it? Investors build and use models like this all the time. Then, I could try my best to quantify the actual probabilities. I guess this is, in some ways, a question that defines one’s commitment to the ways of the quant. Can we assume that the quant with the deepest running conviction would cease to go after the top prize if the model insisted that it was slightly “irrational?”

But should we be striving to act rationally now anyway? This question gets interesting if you think about how to present this decision. If you look at in the sense of would you bet X dollars with a certain set of odds that you will win 6.67, other odds that you will win 3.67 times your money, other odds that you will neither lose nor win money, and a final set of odds that you will lose your money, it sound much more reasonable to use a model and just choose the most rational option. But fantasy baseball isn’t an investment, or at the very least it is not just an investment. There’s glory, enjoyment and trash-talking privileges on the line here. When you think about it in the greater social than mathematical context, it seems that anything except walking head on into a speeding bus is a “rational” risk.