When Winning Means Losing: A Backwards Take on Greatness

In Matthew 19 and Mark 10, Jesus introduces a theme that challenges typical ideas of success: “But many who are the greatest now will be least important then, and those who seem least important now will be the greatest then” (Matthew 19:30, NLT). Mark’s version echoes the same idea after a discussion about wealth and sacrifice. It’s a reversal that feels intentionally disorienting, as if greatness itself is being redefined.

A Rich Man’s Tough Question

In both chapters, these words follow the encounter with the rich man who asked what he needed to do to inherit eternal life. Jesus’ answer—that he should sell his possessions and give to the poor—was too difficult for him to accept. The disciples, watching this unfold, are clearly unsettled. If someone wealthy, respected, and outwardly moral couldn’t meet the standard, who could? Peter even blurts out, “We’ve given up everything to follow you. What will we get?” (Matthew 19:27, NLT). It’s in response to that question that Jesus offers this puzzling reversal.

Wealth, Status, and Shock Value

What’s interesting is how these chapters tie wealth, sacrifice, and status together. In the culture of the time, wealth often signified divine favor, so Jesus’ insistence that the wealthy would struggle to enter the kingdom would have been shocking. Even today, we often equate success with status, accomplishment, or material comfort. This statement turns that entire framework upside down.

Jesus’ words about children in these chapters add another layer. He tells his disciples, “Let the children come to me. Don’t stop them! For the Kingdom of God belongs to those who are like these children” (Mark 10:14, NLT). Linking this to the “first and last” statement suggests that qualities like vulnerability, dependence, and openness might hold more value than traits we typically admire, like self-sufficiency or ambition.

The Big Question

This makes me think about how these ideas challenge not just individuals but entire systems. If those who are “last” in the world’s eyes are somehow “first,” then the structures we build around wealth, recognition, and influence might be completely inverted in this vision of the kingdom. It’s a deeply unsettling idea—this teaching seems designed to provoke reflection rather than provide a simple answer.

Both passages leave the reader with an open question: What would it mean to measure life’s success in this way? For the disciples, this teaching came at a moment when they were trying to understand their own sacrifices. For us, it might encourage a different kind of evaluation—one that doesn’t fit easily with cultural norms, but invites us to pause and consider what really matters.