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My friend Mark Barrett sent the link to Finding Their Way Back , an interesting report on baseball guru Bill James and the Boston Red Sox. If the writer is right about James, he seems to be a class act. The article will be of most interest to the baseball fans among you, and in particular for Red Sox fans and other fans who see the Yankees’ success as one of the things the psalmist lamented in the “Why do the wicked have it so good?” psalms.

There may be another lesson in the story, however. Joe Posnanski writes:

The Red Sox, Bill James believes, fell into what is a pretty common trap for successful people: “After we had been very successful for a long time, we lost sight of the fact that we were still capable of making huge blunders,” he says. “We sort of started to assume that whatever we did would work out.”

This small bit, I believe, explains so many seemingly inexplicable decisions in sports and in life. You get told that you’re smart enough times, and it gets harder and harder to not believe it (just as if your employees or admirers laugh every time you make a joke, you can become convinced that you’re Louis C.K.).

Posnanski mentions all the things that went wrong for the Red Sox after 2007 when they won the second World Series. He mentions “disastrous signings” — and some of them really were baffling — but doesn’t mention the astonishing amount of money the Red Sox wasted on these disastrous signings. It’s one thing to misjudge the future performance of a player, it’s another to misjudge it after offering him tens of millions of dollars.

There is something going on here I don’t really understand. It happens in baseball and in businesses and other enterprises where you really have to deliver.

When people succeed, they start spending money badly. They don’t necessarily buy lots of things, they buy expensive things and things whose value to them is clearly less than their cost. Even when their future success depends on how they spend their money now. Letitia (Mrs. Horace Percy) Smythe-Horsehair can waste money on a diamond necklace without feeling it, but a general manager who wastes money on a hitter already in the downslide of his career gets fired and made fun of in the newspapers and on the radio talkshows, and the kids at school persecute his kids.

Maybe it’s just pride. Presumably such people feel that he who is successful with little will be much more successful with a lot. Most of the time, they wind up like this year’s Red Sox.

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