In May 2021, the Toronto Maple Leafs National Hockey League team lost a seventh and final playoff game—again. The day after their loss, Toronto Mayor John Tory took the unusual step of penning an open letter to Maple Leaf fans in response. His two-page letter was a unique mix of communication genres, including sport communication, political communication, and, with multiple references to COVID-19, health communication. It was also, as we argue here, a unique example of image repair rhetoric in general and sport image repair rhetoric in particular. In this rhetorical analysis, we build on a growing body of sport image repair in the form of open letters, revealing how the interaction of these contexts with Tory’s main focus on the team reveals how his open letter is at a crossroads of intersecting image repair efforts in politic, health, and sport. We draw three primary findings from our analysis, including the possibility that Tory’s letter functioned as an inoculation message, preparing fans to resist discouragement and a dampening of support.