In Matthean research, the quest for a suitable key to the understanding of the sixth woe (Mt 23.27–28) has not yet provided results that are fully convincing. Against the backdrop of Jewish everyday life, the image of positively connoted white tombs seems to have no relevant point of reference. Rather, white is understood as a warning colour in the context of tombs as it is intended to mark and warn against the tombs’ impurity. In contrast to these findings, the article confirms the existence of prominent white graves which were considered beautiful in first-century Judaism: the tombs of the patriarchs at Hebron and the tomb of King David at Jerusalem, both artfully embellished by Herod the Great. In the light of these parallels, the logic of the comparison, which serves as an argument for the woe of Mt 23.27–28, falls into place and perhaps provides an additional insight into Matthew's view of Herod the Great.