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This study explores the possibilities/constraints of coalitional work between a
community-based organization and a local educators union in the context of mobilizing
against a proposal to expand charter school seats in one city. The grassroots coalition delved into the application of interest convergence and critical coalitional theory so as to attempt to engage the union in community-based, anti-racist and anti-oppressive solutions to strengthening public schools while simultaneously working in solidarity to resist privatization proposals including one that would create a unique charter school model that would bypass state laws and potentially dismantle the charter school cap in Massachusetts. The key question explored: How might the lessons learned regarding coalition formation, development and sustainment deepen educational justice struggles?