Rockstar’s Grand Theft Auto franchise continues to receive critical acclaim for its open-world structure that invites emergent forms of play. The live service monetization of Grand Theft Auto V, however, confers a monetary value on in-game items and activities, which fundamentally alters the playspace and recontextualizes discussions of player agency within the attention economy. This essay explores legitimate and illegitimate techniques players developed for earning in-game currency and rebalancing the game’s economy in their favor. In doing so, it reflects on the implication of these practices for our understanding of an implied player role and the significance of transgressive play.