The story of Jesus’ triumphal entry into Jerusalem is one of contrasts. It is the story of the King who came as a lowly servant, on a donkey rather than a prancing steed, not to conquer nations by force but to conquer hearts by love. Yet this is also a tragic story: though his very own people greeted him with shouts of praise and acclamation (Luke 19:38), they failed to truly recognize him as the Savior of their sins: “When he drew near and saw the city, he wept over it, saying, ‘Would that you, even you, had known on this day the things that make for peace!” (Luke 19:41–42). In this sermon, Pastor Dave examines the historical setting and biblical significance of the triumphal entry in order that we might come to hail Jesus as our God, our Redeemer, and our King.