We show that truth conditions for counterfactuals need not always be given in terms of a vague notion of similarity. To this end, we single out the important class of historical counterfactuals and give formally rigorous truth conditions for these counterfactuals, employing a partial ordering relation called “comparative closeness” that is defined in the framework of branching space-times. Among other applications, we provide a detailed analysis of counterfactuals uttered in the context of lost bets. In an appendix we compare our theory with the branching space-times based reading of counterfactuals recently proposed by Belnap.