PURPOSE We examined the clinical outcome of patients with lymph node metastases found at prostatectomy with the goal to identify factors that predict freedom from prostate specific antigen (PSA) progression. MATERIALS AND METHODS We retrospectively reviewed the records of 3,264 consecutive men with clinically localized prostate cancer who underwent extended pelvic lymphadenectomy and radical prostatectomy performed by a single surgeon between April 1982 and March 2003. Patients with pathologically confirmed lymph node metastases and no history of adjuvant treatment were identified. Clinical and histopathological factors were analyzed for an association with time to PSA progression using univariate and multivariable analyses. RESULTS Of the 143 patients (4.4% of total) in the study with nodal involvement 24 (16.8%) were free of disease at last followup (median 6 years). Median time to failure was 2 years with PSA progression occurring as late as 11 years postoperatively in 2 patients. The 5 and 7-year PSA progression free rate in all lymph node positive patients was 26.5% and 10.9%, respectively. A 15% or greater incidence of positive nodes (p = 0.0008) and high prostatectomy Gleason score (ie score 8 to 10, p = 0.008) were independent predictors of PSA progression in multivariate Cox proportional hazards models. Seminal vesicle invasion (HR 1.45, p = 0.063) or positive surgical margins (HR 1.43, p = 0.063) were marginally significant in the multivariate model. The 5-year PSA progression-free rate was 52% in men with less than 15% positive lymph nodes, prostatectomy Gleason score 7 or less and negative seminal vesicle invasion. CONCLUSIONS While the incidence of lymph node positive disease in patients undergoing radical prostatectomy is infrequent in the PSA era, patients with nodal involvement may experience disease progression as remote as 1 decade after surgery. Pathological factors such as the percent of positive lymph nodes, prostatectomy Gleason score and seminal vesicle invasion appear to predict an increased risk of PSA failure in this population.