This article offers a new approach for reconstructing the original form and meaning of Jesus’s legal woe sayings in Matt 23:16-26 (and the parallel in Luke 11:3944) as part of a broader Jewish intersectarian discourse. A close analysis of this unit alongside an early rabbinic source embedded in Mishnah tractate Yadayim 4:5-8 reveals that Jesus’s condemnation of the Pharisees was not unique. His arguments concerning oaths, tithes, and ritual purity belong to a pre-Matthean stratum, and they match a familiar rhetorical pattern condemning the Pharisees’ lenient and compromising approach. According to this pre-Matthean tradition, Jesus drew his argument and depiction of the Pharisees from the current intersectarian debate concerning the essential principles of torah observance. Jesus is portrayed as exploiting current anti-Pharisaic accusations, familiar also from Qumran literature and directed originally against the Pharisees’ distorted conceptions of purity and holiness, as he attempts to uncover their moral faults.