INTRODUCTION: The objective of this report is to describe the oncologic outcomes of men with margin-positive prostate cancer who were managed expectantly following radical prostatectomy. MATERIALS AND METHODS: Between January 1992 and January 2011, 2166 men underwent an open radical prostatectomy by a single surgeon. Of these patients, 1592 (74%) had complete data and met the inclusion criteria of negative lymph nodes and no history of neoadjuvant or adjuvant therapy. This cohort was dichotomized by the presence or absence of at least one positive surgical margin. Groups were compared for differences in recurrence-free and overall survival. RESULTS: In total, 507 (32%) of 1592 patients had at least one positive surgical margin. Clinical and pathological characteristics of these patients indicated more aggressive disease. The median follow up for biochemical recurrence and overall survival was 3.4 years and 7.7 years, respectively. Of those patients with a positive margin, 147 (29%) recurred, with estimated 5 and 10 year biochemical recurrence rates of 31% and 47%, respectively. Multivariate analysis demonstrated that the presence of a positive margin was associated with a 2.45-fold increased hazard of recurrence (p < 0.001). Despite initial observation, surgical margin status was not associated with a decrease in overall survival on both uni- (p = 0.684) and multivariate analyses (p = 0.177). CONCLUSION: Although a positive surgical margin is associated with an increased risk of biochemical recurrence, patients in our series were not at an increased risk of all-cause mortality.