Some of the most understated factors in the study of conflict is the role of border changes. What do elites and citizens think of their country’s fate when their borders are being shrank? And just the opposite: how to set the ultimate territorial goals of a country when its elites and citizens notice that most disputes fall its way? This paper tries to shed light on the current war in Ukraine by zooming out and thinking more empirically about the fates of countries (mostly empires) which lost territory for good, compared to those which made territorial inroads. We zero in on countries whose political roots were built during revolutionary periods, and investigate how these roots-turned-capabilities can be exploited to produce collective outcomes such as wars (negative result) and poverty alleviation and literacy (good results). Territorial gains help cement not only leadership’s reputation but also its connection with society. Revolutionary nationalism is a strong recipe for societal change, but sometimes with the risk of territorial over-reach.