The history of campaigns against apartheid through sport reveals messy relationships between athletes and social movements, advancing recent debates over the possibilities and constraints of sport politics. The anti-apartheid movement coalesced around a transnational sporting boycott to isolate South Africa, but the American tennis icon Arthur Ashe made a series of visits to compete there in the 1970s. Ashe believed in participation as the primary mechanism for change through sport, only later embracing the boycott. When tennis tournaments and rugby tours brought South Africans to the United States, anti-apartheid organizations mobilized their own confrontational protests to interrupt play. As the growing movement won over athletes and South African propaganda turned toward commercial sport spectacle, the special position that athletes occupied provided leverage. However, their magnified legacy also obscured how resistance to apartheid through sport found success in the first place. Despite the appeal of participation as the natural path of progress, strategies of confrontation often proved more effective in the struggle against apartheid. Questioning the politics of participation and widening the frame to consider confrontation changes our understanding of sport politics, looking beyond individual athletes and bringing everyday people off the sidelines.