Chuck Smith emphasizes the significance of the day Jesus entered Jerusalem, a day long awaited by Israel as the fulfillment of prophetic promises of a Messiah. He highlights the people's anticipation for deliverance, hope, and salvation, marking it as a pivotal moment in history when Jesus allowed public worship. However, Smith laments that Jerusalem missed this opportunity by rejecting their Savior, warning that each individual has their own 'day' to embrace or reject God's call. He draws parallels between this event and other historical triumphs, underscoring the thin line between triumph and tragedy, as foretold by Daniel regarding the Messiah's fate.