Jesus' journey to Jerusalem culminates with a note of humility and prophetic triumph. This surprising confluence of events fulfills prophetic imagery particularly from Zechariah. Some 20 times in the book of Zechariah, the phrase: “on that day” appears indicating: A DECISIVE MOMENT OF MESSIANIC FULFILLMENT SIGNALING JUDGEMENT – DELIVERANCE – AND SALVATION. Matthew 21 records this day's events and their powerful history shaping effect which continues to reverberate to our day and beyond. Instead of a chariot pulled by cherubs or soaring on the wings of the wind (as we see the Lord in Psalm 18) Christ chose to enter the City of David as the Son of David, on a lowly beast of burden. Zechariah tells us why and reveals the backdrop to more fully appreciate the triumphal entry of Christ.