Predicated on the finding that most wars stem from a relatively small number of rivalries, some analysts are shifting attention away from general probabilities of state conflict behavior escalating to war and toward modeling why rivalries sometimes (de)escalate in hostility. In this chapter, we reexamine and extend one such effort that is predicated on the assumption that territorial disputes provide the fundamental motor for escalation to war among rivals. Vasquez's (1996) model differentiates two different paths to war for contiguous and noncontiguous rivals. While the model is attractive in many respects, it is doubtful that the major power subsystem, Vasquez's empirical focus in the 1996 study, is the most likely place to find empirical corroboration for an argument stressing territorial issues. Major powers do quarrel over territory but they also have a marked propensity for competing over positional issues. Accordingly, we develop a second theory that allows for variable interests in two types of issues – spatial and positional. Many, but not all, of the same hypotheses that Vasquez derives from his single-issue theoretical focus can also be deduced from the two-issue theory, but now both paths receive equal theoretical attention. Moreover, three more testable hypotheses pertaining to the prevalence of contiguous/noncontiguous rivalries, dyadic versus multilateral wars, and war-joining behavior can also be derived. We can also test the previously assumed linkage between contiguity and territorially focused rivalries. These several new hypotheses and the added explanatory power facilitate choosing between the two war escalation theories.