Agricultural land systems are the result of human interactions with the natural environment, and subjective evidence of socio-economic and environmental interactions has been demonstrated. Nevertheless, it is still difficult to analyze empirically the link between agricultural market and policy, as well as the environmental response due to changes in crop management by local stakeholders. In this study, we propose a cross investigation and analysis to bring the link between vegetation cover, policy, market and farmer's behavior to light. Our methodology is a combination of a rational positive and analogical approach between the quantifiable and non-quantifiable agents on a temporal basis. The method is applied to a dominant mono-crop agricultural watershed in Southern Italy that has been dedicated to durum wheat cultivation. In this region, we studied the relationship between the Common Agricultural Policy (CAP), durum wheat market price, vegetation cover and land allocation. As a first step, we conducted a separate analysis for each factor, exploiting Moderate Resolution Imaging Spectroradiometer (MODIS) satellite observed Leaf Area Index (LAI) to analyze the land vegetation space-time distribution over the period 2000-2014 and three Land Satellite (Landsat) validated images as check-points for the agricultural pattern and CAP's reforms. We used the Farm Accountancy Data Network (FADN) and Eurostat data to investigate the on-farm accountancy and the durum wheat market price changes, respectively. Based on the study period, we developed a storyline of the major relevant CAP's policy changes. In a second step, we conducted a comparative analysis where the CAP's reforms were used as interpretational support, the land allocation and the on-farm accountability for CAP's implementation, the price of durum wheat and the LAI for analytical comparison. We found interesting insights regarding the non-agronomic driving forces of LAI dynamics. The behavior of the individual farmers is influenced by the CAP policy that has been implemented by using profitability as the stimulus for the decision making of the farmer. This explains the correlation of the trend between the market price, the LAI of durum wheat and their associated dynamics.