Abstract: Urban skateboarding events have rapidly evolved into dynamic platforms for both athletic performance and localized economic stimulation. This study employs a behavioral economics framework to investigate fan spending patterns in such events, utilizing real-time data analytics to simulate crowd behavior and economic transactions. Through a hybrid methodology combining observational simulation and inferential statistical modeling, we analyze the determinants of individual spending behavior, including emotional arousal, environmental stimuli, event timing, and promotional influences. The study reveals significant heterogeneity in fan spending based on demographic segments, perceived event intensity, and real-time promotional cues. These findings underscore the importance of psychologically informed pricing and marketing strategies in maximizing both fan satisfaction and economic return. This research contributes to a nuanced understanding of how behavioral economic principles operate in urban sports contexts and offers actionable insights for event organizers, urban economists, and policymakers. Keywords: Behavioral economics; Urban sports; Skateboarding events; Fan spending; Real-time analytics; Consumer behavior; Sports marketing; Simulated data; Event-based economy