Jesus' lament, I believe, centers around the misconceptions the people had for who he was and why he was there. In the words of storyteller Walter Wangerin, Jesus “was not rejoicing in the public acclaim, nor glorying in the advent of his kingdom now. He was crying! He was gazing at the stones of the city and allowing tears to run down his face…the tone was defeat” (The Book of God). The peoples' praise at Jesus' entrance was filled with their own expectations for how Jesus would bring them back into the "good life" - a time in which Israel once again literally reigned in the world as God's people. Essentially, "Hosanna" was filled with their own hopes and dreams. For Jesus, this is something worth crying over.
The story of Palm Sunday, then, makes we question our own lives, our own worship. How do our "Hosanna's" - our worship celebrations - simply project our ideas for the "good life"? Do we, like the crowds in Jerusalem, have misconceptions about what we're celebrating when we remember Jesus? It's these questions that make Palm Sunday bittersweet. Yes, Jesus is our Lord and King, but do we really get what that entails? Or, in the words of N.T. Wright, do we follow "conventional wisdom" in which "the way of the Messiah would be the way of fulfillment and self-aggrandizement: those who wanted to gain their lives would have to fight for them." We're challenged in our definition of faith and discipleship, as Wright continues: "Jesus’ most subversive teaching, in both form and content, consisted in just this: that the way of wisdom meant taking up the cross, dying in order to live” (Jesus and the Victory of God).