This study researches the past, present and future role of ports, specifically the Ports of Tampa and Hamburg linked to their cities. It examines the legal structures of port authorities which play a major role in their economic priorities and impact their cities’ social, environmental and cultural quality of life. From a humanistic perspective, one can look at a port as a place or space. By animating ports, they may provide “ fields of care” over time, and a home with character for the region’s residents. In this case, their success needs to transcend economics, adding qualitative attributes to the region, such as clean air, water, good working conditions, adequate housing, public transportation, recreational provisions, public waterfront access and more. The Port of Tampa’s corporate style and largely state controlled management team prioritized diversification. As a result, the port essentially remained a feeder port. It depends on shipping phosphate (a non renewable resource), fertilizer, scrap metal, petroleum and other general cargo commodities. The port serves main (hub) and container ports which are more lucrative and environmentally less challenging. The Port of Hamburg, on the other hand, controlled by an elected local Senate, became a container hub port early on, and planned its future accordingly. Tampa’s traditional housing around the port was dissected; shopping, service and recreational areas around Tampa’s city core deteriorated, when Interstates 275, 4 and the Cross Town Expressway were constructed. Suburbs in rural areas were developed with little regard for public transportation infrastructure, recreation facilities, and pedestrian and bike paths. Most of Tampa’s waterfront, owned by its Port Authority, is leased out and fenced off to the public access. Redeveloped expensive and mostly empty downtown gentrified residences face parking garages, oil tanks, phosphate stags and scrap yards. Much of Harbor Island, close to downtown, is gated and gentrified. The Port of Hamburg, in contrast to the Port of Tampa, redeveloped an uninhabited warehouse region of its Port, named it Hafen City, thereby adding 40 percent to the core of the city. This cohesive theme is in the process of providing jobs, housing, public waterfront access, shopping, green spaces, museums a concert hall, a theater and more. Light-rail, subways trams, buses, pedestrian and bike paths link the Hafen City to the traditional city center. Hamburg’s waterfront remains open to the public by law. A comparison of both port cities shows that the Port of Tampa’s largely state controlled corporate style management team prioritizes short term economic results over an extended future planning at the expense of the region’s social, cultural and environmental climate. The Port of Hamburg’s management team, installed by the locally elected Senate, promotes the City’s economic, social, cultural and environmental quality. The above findings, suggest that developments of ports and their cities under democratically elected governments may produce various qualitative outcomes depending on the demand and supply curve of their residents’ input.