In games such as squash, it is generally assumed that weaker players maximize their chances of winning when they play as few points as possible against superior opponents. The failure of squash players to recognize this and to prefer shorter games against stronger opponents has been cited multiple times in the literature as evidence of the foibles of lay decision makers. This error has been categorized as an error of application, attributed to the representativeness bias, and ascribed to sudden death aversion. Decision analyses presented here demonstrate, however, that under certain conditions the maxim for weaker players to minimize the number of points played against better players does not lead to optimal decisions. This holds true for choices about how many points to play in tiebreakers and the choice between playing games to 9 or to 15 points. The analyses illustrate the danger in overgeneralizing about lay tendencies to make irrational or suboptimal choices without careful examination of the task environment. The analyses also illustrate that optimization will not necessarily involve a corner solution that minimizes or maximizes total number of points played even for such a straightforward game as squash or in analogous circumstances off the court.