Social media has become an important frontier in the sport sponsorship paradigm (Dees, 2011), offering brands a powerful mechanism to stimulate consumer engagement (Vale & Fernandes, 2018). Despite this potential, the extent to which social media content, as part of a sport sponsorship’s leveraging activities, can yield consumer engagement behaviors is unknown. Thus, the purpose of this study was to examine the impact of integrating sponsors into the social media posts of sport organizations on fan engagement. A total of 13,542 Instagram posts from four professional sports teams were extracted from 2017–2019. A regression analysis revealed that sponsored content negatively affected engagement levels. Consequently, brands need to be more cognizant that simply sponsoring content in an inauthentic, forceable manner may not yield the results they are seeking through their association. Furthermore, sport organizations need to reconsider their social media strategy, working with partners to organically embed sponsors into content.