While the category shift of deverbal prepositions has been well documented in grammaticalization studies, its accompanying process of subjectification remains underexplored. Adopting a constructionist perspective, this article addresses the gap by analyzing data from the Corpus of Historical American English. We present a multivariate analysis of the deverbal preposition considering to examine the role that subjectification has played along the way to it becoming a preposition over the past 200 years. Specifically, we investigate whether the two grammatical variants, participial and prepositional considering, can be anchored in context, focusing on a set of subjectivity indicators and their gradual changes over time. The findings are twofold. First, the two variants can be distinguished by six contextual features, namely subject animacy, subject person, contextual polarity, presence of degree modifiers, presence of modal auxiliaries and genre. Second, over time, there is an increasing correlation between the prepositional variant and levels within contextual features that indicate greater evaluative subjectivity. Previous scholarship has debated whether subjectification is independent of grammaticalization. This study contributes to this discourse by illustrating how various facets of subjectification may interact and manifest to varying degrees within the process of grammatical change.