Cities are like “heterotrophic organisms” because they are dependent on inflows of air, water, food, matter, and energy. Unlike nature, they pollute their own habitat through the production of waste outflows and emissions, extending beyond their own footprint. Data on the ecological footprint of cities have quantified, emblematically, the imbalance between in- and outflows but also what remains: polluted air, water, and soil. The rapid growth of urbanization is a matter of serious concern, but as a part of new development, it can be turned around with an approach in which cities become an “autotrophic organism”. In 2012 Taranto, a coastal city in Southern Italy with an important commercial and military port, was declared as the city “with the highest risk of environmental crisis” in Italy due to a large industrial area developed in the proximity of a highly populated urban settlement. The cause of pollution, a steel production plant, directly employs approximately 12.000 people and another 8.000 contractors indirectly, making it Taranto’s main economic driver. The conflict between economy and environment in the city of Taranto, make it a peculiar case study to be approached with the concept of a Democratic Landscape. This concept reads the territory beyond the natural environment, also recognizing the wellbeing of the inhabitants. After the analysis of a Democratic Landscape in relation to the concept of an “autotrophic organism”, this contribution explores the transformation by regeneration of the ecosystem and the economic regime. In redeveloping a city like Taranto, changing its function from a heterotrophic organism to an autotroph organism, the approach of the so-called “linking open-loop system circularity” is more appropriate. It more adequately describes the system than what is commonly understood for circularity at the building scale of “reduce, reuse, recycle of resources”. Circularity as an attitude brings together many elements that can be considered generic for each project: it can be about recycling or reuse, cutting costs or time, and output of CO2 through reducing material inflow and the transport of materials. In the context of the Democratic Landscape and an autotropic organism, the approach of “linking open-loop system circularity” is tested on two scales in Taranto. One, on the large scale, proposing multiple reuses of agricultural crops after remediation and two, at the local scale, in rebuilding a portion of the city by reusing the demolished buildings materials. The need to rethink and redesign the flow of resources such as building materials, water, food, and energy is essential to the future sustainability of cities. It involves thinking about how to use existing resources rather than dispose of them as in the linear model. It also means establishing new economic models in order to make a sustainable city, flows of intelligent growth and the creation of an identity for a communal sense of belonging. Together, these create a democratic, autotrophic landscape that can sustain a future.