Brad Rowe explores the complexities of cannabis legalization, emphasizing the challenges and opportunities it presents globally. This review features insights from policymakers, advocates, researchers, and industry leaders, reflecting on the transition from prohibition to regulation. Key themes include balancing equity, public health, and economic goals while navigating the competition between legal and illicit markets. Andrew Freedman, Colorado’s first Cannabis Czar, stresses the importance of careful implementation to avoid logistical pitfalls and supports fostering small businesses akin to the craft beer industry. Jay Shukle of Alberta Gaming highlights Canada’s lessons in managing supply–demand mismatches and restrictive regulations. Beau Kilmer of RAND delves into economic dynamics, warning of the risks posed by high-potency products and proposing THC-based taxation. Contributors like Shaleen Title and Amy O’Gorman Jenkins champion equity, calling for deliberate, data-driven approaches to ensure fairness for marginalized groups. International perspectives, such as Alejandro Hope from Mexico and Simon Howell from South Africa, illustrate how legalization impacts social justice and economic reform, emphasizing the interconnectedness of global drug policies. Public health concerns feature prominently. Experts like Dr. Daniele Piomelli and Dr. Bonni Goldstein advocate for cannabis’ medical potential, while Jon Caulkins warns of regulatory capture and shifting consumption patterns. Others, like Amber Senter, highlight barriers small, equity-focused businesses face amid federal restrictions and market consolidation. Federal legalization’s future raises opportunities and risks, such as the potential for interstate commerce and industry consolidation. Contributors stress the need for thoughtful policies to balance innovation, public health, and equity. The review underscores the importance of continued collaboration and vigilance to ensure cannabis legalization achieves its potential as a tool for social justice, economic opportunity, and public health improvement. Through diverse voices and experiences, this work paints a nuanced picture of cannabis policy as an evolving patchwork, requiring adaptability and inclusion to navigate its complexities.