The role of philanthropy in the well-being of LGBTQ communities in Canada is questioned from the premise of the developing queer liberation theory. Surface level understandings of LGBTQ community well-being are deconstructed to account for politicized differences that exist therein. Examined is the role of philanthropic organizations in contributing to LGBTQ community well-being, given the historical marginalization of gender and sexually diverse communities, and what currently constitutes potential philanthropic support and what does not. Foregrounded by the socio-legal recognition of Canada’s gender and sexually diverse yet underscored by the uneven levels of well-being due to the socio-political divides within these communities–not generally known to the mainstream public–provides a complicated picture of philanthropic organizations’ contribution, both Canadian and global, to LGBTQ community well-being. Revealed through critical analysis are the socio-political implications of the relations between philanthropy and Canadian LGBTQ communities with the need to recognize the multiplicity of differences within these communities, how advocacy is regulated in Canada, and the implications of these variables on policy, programming, funding, community development, well-being, and ultimately democracy. All of these components contribute to a nuanced understanding of the complex relationship between philanthropic organizations and the well-being of Canadian LGBTQ communities, with philanthropies urged to take a reflexive approach to their work. © 2021, The Author(s), under exclusive licence to Springer Nature Switzerland AG.