Chronic diseases constitute the leading cause of mortality in the western world, have a major impact on the patients'quality of life, and comprise the bulk of healthcare costs. Nowadays, healthcare data management systems integrate large amounts of medical information on patients, including diagnoses, medical procedures, lab test results, and more. Sophisticated analysis methods are needed for utilizing these data to assist in patient management and to enhance treatment quality at reduced costs. In this study, we take a first step towards better disease management of diabetic patients by applying state-of-the art methods to anticipate the patient's future health condition and to identify patients at high risk. Two relevant outcome measures are explored: the need for emergency care services and the probability of the treatment producing a sub-optimal result, as defined by domain experts. By identifying the high-risk patients our prediction system can be used by healthcare providers to prepare both financially and logistically for the patient needs. To demonstrate a potential downstream application for the identified high-risk patients, we explore the association between the physician treating these patients and the treatment outcome, and propose a system that can assist healthcare providers in optimizing the match between a patient and a physician. Our work formulates the problem and examines the performance of several learning models on data from several thousands of patients. We further describe a pilot system built on the results of this analysis. We show that the risk for the two considered outcomes can be evaluated from patients'characteristics and that features of the patient-physician match improve the prediction accuracy for the treatment's success. These results suggest that personalized medicine can be valuable for high risk patients and raise interesting questions for future improvements. Copyright 2011 ACM.