As local, informally run, volunteer groups, grassroots associations have been noted for their role in generating social capital, citizenship, and civic engagement. However, while the benefits of such associations have been theorized, there is a lack of empirical studies that investigate the contemporary context of grassroots associations. Presented here is a descriptive case study of a local softball league in Southern Ontario. What the case shows is an organization that faced significant challenges in maintaining its informality within a social environment that favours formality. The consequence for the league members was an increasing sense of dissatisfaction and frustration stemming from their interaction with local institutions, lack of specialized knowledge, and declining support from association members. In sum, it appeared that this contemporary grassroots association faces a dilemma: while formalization may ameliorate the league failures, it also decreases the potential for social benefits related to social capital and civic engagement.