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In this article, I examine the distributional properties, emergence conditions, and development of the habitual verbal head pflegen 'use(d) to' in the history of German. Synchronically, I argue that Present-day German possesses subject to subject raising verbs and that they can all be brought down to a common denominator: They allow promotion of the embedded subject into the matrix subject position (= A-movement). However, at the same time I argue that German subject to subject raising verbs differ and that their heterogeneity follows from their semantics. What all this boils down to is that German subject to subject raising verbs do not form a uniform class, neither semantically nor syntactically. As for pflegen, I account for its syntactic peculiarities referring to its functional status, i.e., the status of being a habitual head. Diachronically, I show that pflegen grammaticalized into an AspHAB-head in the transition from Old High German (750–1050) to Middle High German (1050–1350) and that this grammaticalization process restricted the way it behaves in Present-day German. [ABSTRACT FROM AUTHOR]