Suppose that a gambler starts with a fortune in (0, 1) and wishes to attain a fortune of 1 by making a sequence of bets. Assume that whenever the gambler stakes an amount s, the gambler's fortune increases by s with probability w and decreases by s with probability 1 − w, where w < 1 2 . Dubins and Savage showed that the optimal strategy, which they called 'bold play', is always to bet min{f, 1 − f }, where f is the gambler's current fortune. Here we consider the problem in which the gambler may stake no more than at one time. We show that the bold strategy of always betting min{ , f, 1 − f } is not optimal if is irrational, extending a result of Heath, Pruitt, and Sudderth.