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There has been a challenge regarding the number of donkeys ridden by Jesus during the triumphant entry into Jerusalem. This is exacerbated by the notion that Matthew was unaware of Hebrew poetic parallelism in his allusion to Zechariah’s prophecy and portrayed Jesus as riding two donkeys. Matthew’s gospel contrasts the other three evangelists, who report only one donkey in their accounts. In this article, an exegetical analysis of Matthew 21:2 reveals grammatical and lexical considerations that clarify Matthew’s apparent divergence. It has been established that Jesus mounted a young male donkey that had never been ridden before. The final personal plural pronoun αὐτωv in Matthew 21:7, read together with the final coordinating conjunction καὶ, has been shown that it relates to the garments upon which Jesus sat, not on the two donkeys. The study also shows that when the final καί in Matthew 21:5 is read epexegetically as an adverb or ascensive conjunction and translated as “even,” the allusion to Zechariah’s prophecy proves that Matthew was aware of Hebraic poetic parallelism. The same holds for the Hebrew text in Zechariah 9:9, where the waw conjunction is considered epexegetical.