Studies on the effect of leader humility generally portray leader humility as beneficial, whereas a minority of studies recognize potential negative influences. This is probably most clearly the case in the study of organizational citizenship behavior (OCB) for which both positive and negative relationships with leader humility have been established. We advance the analysis of the leader humility—OCB relationship by proposing that leader humility has diminishing returns, such that its effects are positive at lower levels but at higher levels turn negative. We argue that high levels of leader humility boost followers’ views of themselves, as expressed in higher levels of pride, which gives rise to psychological entitlement. Such entitlement in turn reduces OCB. This suggests a model in which leader humility has a curvilinear, increasing returns, relationship with follower entitlement, mediated by follower pride, that in turn mediates a curvilinear, decreasing returns, relationship with OCB. Results of a multiwave, multisource survey supported these predictions.