This Article examines the dynamic intersection between freedom of speech and equal protection, with a particular focus on the race and LGBT equality movements. Unlike other works on expression and/or equality, the Article emphasizes the relational and bi-directional connections between freedom of speech and equal protection. Freedom of speech has played a critical role in terms of advancing constitutional equality. However, with regard to both race and LGBT equality, free speech rights also failed in important respects to facilitate equality claims and movements. Advocacy and agitation on behalf of equality rights have also left indelible positive and negative marks on free speech doctrines, principles, and rights. The free speech-equality relationship underscores several important lessons regarding reliance on speech rights to advance constitutional equality. Moreover, through a comparative analysis, the Article demonstrates that freedom of speech intersects in distinctive ways with different types of equalities. The Article’s general lessons and comparative observations carry important implications for future equality movements, including the current campaign for transgender equality.