Taylor Swift has lived half her life at the centre of a music industry maelstrom: wildly successful, she built her career at a time when the record industry was just emerging from a decade-long struggle with technological change and industrial and economic upheaval. In this context, Swift stands out as a peculiar anomaly: she can move product (selling millions of physical CDs in a post-CD era), make daily use of social media like Instagram and, simultaneously, shun the blandishments of streaming media. She has called out industry giants, such as Apple and Spotify, on behalf of artists’ rights but partnered with them when it was advantageous to her. This article explores Taylor Swift’s status as pop icon, businesswoman, and advocate, looking for the strategic links that bind these threads in her career and public persona. In particular, the article addresses the apparent power that Swift wields as a celebrity and, also, the limits of that power in an ever-changing industry environment.