The 1992 World Exposition marked a pivotal moment in Seville’s urban and transportation development, fundamentally reshaping the city’s relationship with the Guadalquivir River. This study examines six innovative bridges constructed for the Expo, analyzing their technical, urban, and symbolic significance, and exploring how artificial intelligence could enhance similar future projects. These infrastructures not only improved connectivity but also catalyzed a comprehensive process of urban regeneration, transforming Seville’s spatial structure, mobility, and identity. The bridges-including the iconic Alamillo Bridge, the functional Barqueta Bridge, and the strategic Centenario Bridge-represent a watershed in civil engineering that addressed long-standing urban challenges by connecting previously isolated areas and redesigning the river’s urban interface. Beyond their technical achievements, these bridges became symbolic landmarks of Seville’s modernization, reflecting a bold architectural vision that merged functionality with aesthetic innovation. The study explores how these infrastructures facilitated territorial expansion, revitalized urban areas, and created new economic and technological spaces. Additionally, it examines the potential of AI in future infrastructure design, highlighting how data-driven approaches can optimize structural engineering, streamline construction processes, and enhance urban mobility through specific software applications and real-world implementations. Ultimately, the Expo ‘92 bridges demonstrate how strategic infrastructure can reshape urban landscapes, serving as a model for innovative and adaptive urban development, enhanced by the capabilities of artificial intelligence.