First Timothy 2:1–7, written under Paul’s name, is one of the few Pauline passages (along with Rom 13:1–7) which provide early Christian communities with explicit instructions on how they engage and negotiate the Roman empire. This paper focuses on the first two verses (1 Tim 2:1–2) of the passage, examining the exhortation that prayers “on behalf of kings” (hyper basileōn) should be made. In doing so, the paper aims to explore the ambivalent and complex nature of this pseudepigraphal document’s position vis-à-vis the empire. First, I will critically survey the history of interpretation of this passage from the late nineteenth century to recent scholarship (e.g., Gill 2008, Maier 2013, Hoklotubbe 2017), thereby indicating the possibility of further discussion. Secondly, by employing traditional modes of investigation, i.e., historical-critical and philological methods, I will demonstrate the ambiguity stemming from the language of the passage itself. Finally, through Homi Bhabha’s theoretical lens, I will explore the ways in which the prayers on behalf of basileis in 1 Tim 2:1–2 may have created colonial anxiety in the imperial gaze. The paper also has implications for faith-communities in the contemporary world, as prayers for leaders (both religious and secular) are still widely practiced.