School fundraising is known to reproduce inequities in schools, yet it remains common practice in Ontario, Canada; findings from a critical policy analysis of an advocacy group's efforts to change fundraising policy help explain why this is the case. Adopting a discursive understanding of policy, the study used rhetorical analysis to identify how the group has engaged in a decades-long struggle over the meaning of fundraising policy. The findings of the rhetorical analysis were examined in light of an historical narrative of Ontario's social context to understand how the policy's contexts have constrained the group's influence. The study's findings demonstrate that challenging school fundraising by defining the policy as a problem of equity is not strong enough to overcome neoliberalism's pressure on parents to provide their children with educational advantages, a trend toward privatization in public education, neoconservative interests in reduced government spending, Canadians' belief in meritocracy, and historical fundraising practices and dominant meanings. Further, the continuance of school fundraising even after Ontario's government introduced policy that explicitly addressed the group's concerns about equity and aimed to limit the practice challenges traditional notional of group influence and success in policy processes.