As Nassim Taleb reminds us, “Nothing is more permanent than ‘temporary’ arrangements.” In today’s volatile sports landscape, lawyers advising athletes, agents, and institutions face just that — shifting rules and unpredictable risks. This CLE program examines current legal and compliance challenges in professional and collegiate sports, with case studies from the NFL, NCAA, and Washington’s WIAA. Topics include managing high-profile and high-maintenance clients, navigating ethical gray areas, and anticipating emerging regulatory trends that shape the modern sports industry.