Objective: To test the relationship of smoking and aggressive prostate cancer in men undergoing radical prostatectomy. Methods: A retrospective analysis of 2290 men who underwent radical prostatectomy from the Shared Equal Access Regional Cancer Hospital database from 2000 to 2013 was carried out. There were 1592 (70%) non-smokers and 698 (30%) smokers at radical prostatectomy. Logistic regression was used to examine whether smoking predicted Gleason score (≥4+3), margin status, extracapsular extension or seminal vesicle invasion. Linear regression was used to test the relationship between smoking and tumor volume. Results: Smokers were younger, more likely to be black, had lower body mass index, higher pathological Gleason score, more positive margins and extracapsular extension (all P<0.05) versus non-smokers. On crude analysis, smoking was associated with positive margins (odds ratio 1.32; P=0.003) and extracapsular extension (odds ratio 1.26; P=0.036). After adjusting for multiple clinical factors, smoking remained associated with a 19-35% increased risk of every adverse feature studied, though only the association with extracapsular extension reached significance. On multivariable analysis, a trend for smokers to have larger tumor volumes (geometric mean 5.8 vs 5.3g; P=0.062) was found. Conclusions: In patients undergoing radical prostatectomy, there seems to be a trend for smokers to have worse pathological features compared with non-/former smokers. If confirmed in future studies, smoking should be considered a modifiable risk factor for aggressive prostate cancer.