A striking feature of Confucius' grief at the death of his beloved disciple Yan Hui is its profound intensity, an intensity detectable nowhere else in the Analects. Like his disciples, the reader of the Analects may be puzzled by the depth of Confucius' grief in this instance. In distinct accounts, Philip Ivanhoe and Amy Olberding bring some measure of intelligibility to the Master's grief. While partially plausible, I think their offerings on the matter fall short of being fully satisfying. Specifically, I argue that Olberding's proposal that Confucius loses certain developmental avenues after Hui's death should be augmented with the claim that the great depth of his grief largely follows from the importance of Confucius' expression of virtue in the lives of his disciples. It was Yan Hui who best facilitated his Master's expression of virtue, and with Hui's passing, Confucius loses an avenue to a robust expression of virtue, a loss he laments deeply.