Ukrainian parliamentarism and constitutionalism have a long history. Its brightest episode occurred 100 years ago, in 1917–1921, when the Ukrainian activists tried to cope with the breakup of the Romanov Empire by suggesting various projects of its reconstruction. In this article, I argue that the history of these projects began at least half a century earlier, when a young professor of history at Kiev University, Mykhailo Drahomanov, started to reflect upon future reorganization of the Russian Empire into a parliamentary state. Being an ardent advocate of turning the empire into a representative democracy, Drahomanov still felt uneasy about unapologetic support of parliamentarism. Having embraced Proudhonian idea of anarchy or self-government, he realized that the existence of parliament was not a universal cure for all political ills of the Russian Empire, especially for the main one—extreme state centralization. Hence, his views of political reconstruction of the empire did not necessarily mean transforming it into the Russian Republic. It seems that a reasonable and reasoned monarch, who could turn the empire into a federal state with a wide local self-government, would totally fulfill Drahomanov’s ideas of future Russia. His enormous influence upon the pre-war Ukrainian intellectuals explains why only few of them seriously discussed an idea of Ukrainian state independence in 1917.