This article reports on a study of 384 decanal appointments and reappointments and examines Canadian university deans' demographics and career paths. The study focused on four variables: gender, race, experience, and provenance; and analyzed variations across faculty and university types. The findings show that the great majority of Canadian university deans possess a Canadian background, with half of them being recruited internally, and that proportions of non-White and female deans mostly align with those of the professoriate. However, the study reveals a pattern of upward cumulative attrition suggesting that structural barriers to success, perseverance, and promotion are shaping non-White and female deans' career paths. Finally, data suggest that about 40% of Canadian university deans are reappointed for a second term.