The 2019 Directive on Copyright in the Digital Single Market represents an intriguing departure from the anticipated path of liberalisation in public policy. While it includes provisions seemingly aligned with the liberalisation of the Digital Single Market by relaxing digital copyright enforcement, it also introduces mechanisms that bolster digital copyright protection, signalling a shift towards market regulation. This paper explores why and how Jean-Claude Juncker’s European Commission proposed a directive featuring robust regulatory elements despite initial promises of copyright deregulation within the Digital Single Market. Combining insights from political economy and political sociology, I examine the concept of ‘political work’ as the practice of promoting, defending, and implementing a choice of public action. Within this framework, I identify a managerial dimension of political work involving political practices that influence the institutional structure and management of public action. Utilising a qualitative methodology involving twelve in-depth interviews with Commission officials conducted between 2018 and 2021, alongside document analysis, I demonstrate how Jean-Claude Juncker and his cabinet’s managerial political work, encompassing organisational reforms within the Commission, played a pivotal role in steering the proposed policy towards regulation.