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Abstract
<jats:p>SUMMARY This article provides a comprehensive exegetical analysis of the “woe sayings” in Matthew 23:13—32, exploring their linguistic, theological, and historical dimensions. The study traces the origin and semantic range of the term “woe” (οὐαί) in the Old Testament, Septuagint, Second Temple literature, and the New Testament. Special attention is given to the prophetic and lamentational functions of the “woe” formula, demonstrating its dual role as both condemnation and compassionate grief. By examining the interplay between Hebrew and Greek usage, as well as the broader cultural and literary contexts, the article highlights the theological significance of the Matthean woes, emphasizing their function as both prophetic judgment and an urgent call to repentance. The analysis contributes to a deeper understanding of biblical rhetoric and the interpretive framework of prophetic speech.</jats:p>