The excitement around investing in cannabis is obvious and undeniable. It shows up in headlines on a daily basis, and investors agree that the time to get involved is before federal legalization normalizes returns, not after. But when will that be? Most will readily say that legalization is going to happen, but very few can tell how or when it will happen. Still fewer can coherently explain the confused, fractured legal status of cannabis at the state level or the many nuanced ways cannabis could experience a de facto legalization that would stimulate huge growth in related capital markets. In this article we outline the myriad political pathways cannabis could take towards legalization, and just how soon it could happen.