In the USA, legislation continues to be debated, discussed, and passed about “divisive concepts”—specifically anti-CRT in K-12 and anti-DEI in higher education. While this manufactured crisis has crept its way into educational institutions across the country, we wonder if our neighbors to the north are having similar conversations, and if so, what those conversations look like. On its face, much of the educational discussion in Canada is centered positively around antiracism and the need to decolonize educational spaces. However, even such seemingly progressive discussions hide the prevalence of white supremacy. In Canada, “equity” work is preferred as a palatable alternative to the more challenging work of calling out white supremacy directly. That is, equity work is a means to gloss over how colonial systems continue to perpetuate disproportionality and hinder the success of minoritized students. In the USA, the blunt display of power through legislation underscores that white comfort is an anathema to progress for marginalized learners. A tie that binds in both settings is the balance between white comfort and white threat. While presented differently, they hold a similar effect. Given that the USA and Canada share some similarities regarding educational approaches, as well as white supremacist historical roots, in this chapter, we look at the scholarly and popular conversations around education, CRT, and DEI in the USA and Canada to understand if what is occurring in the USA around anti-CRT and anti-DEI may be bellwethers for Canada. We identify implications for leading educational systems in these national contexts in the face of white comfort, white threat, and legislation aimed at so-called divisive concepts in educational systems.