This article empirically measures the role of “contextual intelligence” Nye, 2008 to evaluate effective political leadership based on intuitive factors dealing with political situations over time. This study includes a case study that analyzes the importance of the use of contextual intelligence related to the leadership of the president of the Murcia region Spain, Ramón Luis Valcárcel, one of the most popular presidents who served as a Spanish regional leader for the longest amount of time. Data were gathered from three representative surveys conducted in three consecutive regional election campaigns 2003, 2007, 2011 to measure the extent to which Valcarcel’s leadership public perceptions were associated with his strategic link to specific issues and attributes. Results showed correlations between his public image and perceptions about public prioritized issues each time and attributes connected with citizen expectations demonstrating the effectiveness of the contextual factors for constructing political leadership along time.