The Loophole We Keep Looking For in the Gospel
The Gospel today leaves no room for the version of faith that costs nothing.
Dear friends —
Letters from Leo is publishing daily Lenten reflections through Easter, available exclusively to paid subscribers.
Each meditation will explore what it means to follow Jesus more faithfully amid American civic and political life — not as partisans first, but as Christians whose consciences are shaped by the Cross.
Lent is a season of repentance, renewal, and resolve.
It is a time to confront our idols, strip away our illusions, and allow the light of God’s redeeming love to search and purify our hearts.
I hope you will walk this forty-day road with me — as your brother and fellow sinner — embracing prayer, sacrifice, and deeper conversion, and allowing the God of liberation to claim every corner of our lives and our public witness in an age of creeping authoritarianism.
“Do not think that I have come to abolish the law or the prophets. I have come not to abolish but to fulfill.” — (Matthew 5:17)
I was educated by the Jesuits, so let me admit something: I love loopholes.
Tax codes, terms of service, employee handbooks — I read them not to understand the spirit of the rule but to locate the gap.
The entire consulting industry exists to help institutions comply with the letter of the law while violating its purpose. We have turned avoidance into an art form.
The same instinct has colonized the way we practice faith.
Jesus, in today’s Gospel, closes every exit. “Do not think that I have come to abolish the law or the prophets,” he tells his disciples. “I have come not to abolish but to fulfill.” And then the devastating follow-up: not the smallest letter, not the smallest part of a letter, will pass away. Whoever breaks even the least of these commandments — and teaches others to do so — will be called least in the kingdom of heaven.
There is no loophole in this passage. Every clever reading that might let us off the hook dissolves on contact.
This is where the Gospel collides with the way many American Christians actually live.
We have become experts at sorting commandments into categories: the ones that apply to other people and the ones we can safely set aside. Love your enemies? Aspirational, we tell ourselves.
The command to sell what you have and give to the poor gets filed under metaphor. Welcoming the stranger somehow became complicated.
We treat Jesus’s most demanding teaching the way we treat computer software updates — clicking past the terms we never intend to follow.
Moses, in the first reading from Deuteronomy, saw the same danger thousands of years ago.





