In 2005, after the making of the Constitution of Iraq and the making of Sudan's Comprehensive Peace Agreement, many analysts expected the imminent break-up of Iraq, and that the South Sudanese would eventually opt for federalism and power-sharing rather than secede from Sudan. Six remarkable parallels in the histories of Iraq and Sudan suggest that analysts should have predicted that the Kurds and the South Sudanese would have been equally ardent secessionists in the early twenty-first century. Yet Kurdish nationalist leaders chose federalization in and after 2005, whereas South Sudanese nationalists eventually chose secession after a brief federal power-sharing experiment. The different choices of the respective nationalist leaders were therefore critical, but some plausible explanations of their different choices do not withstand scrutiny. The differing outcomes, so far, are necessarily but not sufficiently explained by the different geopolitical neighbourhoods of Iraq and Sudan. The author suggests that secessions are also driven by political parties who are willing to downsize their state rather than modify the existing regime, and by nationalists who calculate that they are unlikely to have political pivotality in a federal democracy. One implication is that federal power-sharing bargains have a better chance of working in deeply divided places when potential secessionists believe that they may have political pivotality within a federation.