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Civil war is a contest where parties attempt to capture territory. Often, this requires capturing key cities--revolutionaries must threaten the capital, while secessionists must threaten regional capitals. Yet, some rebels never advance on cities and others advance only after a significant duration. If attacking and capturing key cities is crucial to gain concessions from the government, why do some rebels never make these advances and others are slow to attack? Previous scholars focus on an opportunity logic, where stronger rebels are better able to spread the fight. However, this explanation ignores that civil war is about politics. Rebels must consider their constituencies' demands (i.e., grievance) and their value of the status quo (i.e., greed). Since governments attempt to block rebel advancements, only insurgents with lower sensitivity to the costs of war and those with a lower value from the status quo more rapidly challenge regional and national capitals. We test this argument using georeferenced event data and find that rebels controlling resource rents are less likely to challenge new cities. Thus, profitable rebels are less likely to upset the status quo.