Prodigal Insights

Dr. Kenneth Bailey — The Cross and the Prodigal

It was the fall of 1989 — the worst fall of my life.

I dropped into a warm bath.
Clothes still on.
Water still running.

From my dad’s pastoral library, I had grabbed a book: The Cross and the Prodigal, by Dr. Kenneth Bailey.

I read it cover to cover.

Then I sprang out of that bath.

Something had shifted.
Something had clicked.

That fall no longer had the last word.

Ever since, I have been trying to put words around that moment. That journey has kept me warm, with the water still running.

Over time, correspondence with Bailey became friendship.

He had spent forty years in the Middle East, teaching, studying, and unearthing buried meaning in Scripture through culture, context, and original languages.

Bailey loved systematic theology. I was a technical systems architect.

Different disciplines, same instinct: trace the structure, follow the meaning, find what is hidden beneath the surface.

My questions kept refilling.

His letters kept flowing.

These are some of the prodigal insights that began in that bath — and never stopped running.

The Bulletproof Prodigal

When Jesus told the prodigal son parable, it wasn’t a campfire story. It was a use case.

Two words I’d hear a dozen times a day in my profession. A use case is a story told with a purpose. You examine it from every angle. You stress-test it. You find out whether it’s bulletproof.

The Pharisees had a challenge for Jesus: why does he eat with sinners? They wanted it settled. So he gave them a use case that couldn’t be broken.

Enemy in the Family

Characters

It was a masterstroke, to my mind, that Jesus cast both Pharisees and sinners in one family.

The Pharisees had built their lives around separation — keeping themselves clean from sinners, refusing to eat with them, treating sin as a defilement God had commanded them to flee. Their holiness code wasn’t cruelty for its own sake. It was their devotion to God. They worked full-time jobs, then studied Torah late into the night, following the rules to the letter.

They worked hard to avoid sin. Sinners played in it.

Putting both groups in the same family — the same house? That was a big ask.

The Most Important Question

“What does the character want?” is the single most-quoted principle in acting and directing craft. It’s asked at every level: the whole story, the scene, and the beat — the smallest unit of story.

Director Elia Kazan (On the Waterfront, A Streetcar Named Desire) put it plainly in Kazan on Directing: “I put terrific stress on what the person wants and why he wants it.” Yale Teachers Institute

Jesus, as the director of the prodigal son parable, casts the father as his protagonist — the father who represents both God and Jesus. And we learn exactly what the father wants when the question comes a second time: “Why do you eat with sinners?” (Matthew 9:10–13). Jesus answers by quoting the Old Testament, Hosea 6:6: “I desire hesed, not sacrifice.”

Hesed is covenant love — but love that comes down before it goes around. The stronger one holds the umbrella and draws the beloved under it. He gives first, beyond what is owed, before anything is returned. The answering love is real, but it is the fruit His love creates — not the price of admission. Not love earned between equals. Love that comes down, and holds.

I know that storm from the inside.

With my dad, I’ve never laughed harder. Sometimes so hard I couldn’t breathe. Yet beyond a shared joke, a beer, a movie, or a round of golf, my dad never held on to what mattered to me. As long as things stayed “fun,” all was well.

My relationship with my dad was limited. But knowing that both the God of the Old Testament and Jesus of the New Testament desire hesed changed me at my core.

A Corpse Either Way

To my mind, Jesus wanted to show the Pharisees where their framework led: no hesed, no restored relationship between the father and the prodigal — and, likely, a corpse either way.

The Pharisees thought like lawyers. Facts first, emotions later. I knew the instinct, because it was mine. I wanted a bulletproof use case — proof solid enough to rest my trust on. My emotions could trail a step behind the facts; I trusted they’d catch up.

Worthless — by every measure that was supposed to matter.

By the law’s measure, he looked prodigal.
By the village’s measure, he looked prodigal.
By the shape of his repentance, he still looked prodigal — returning for bread before he returned for the father.
By the shame in his own heart, he felt prodigal.

And under that framework, he was already a dead man — whichever way he turned.

Stay in the far country, he’d starve to death.

Come home, and he’d face, as Bailey reconstructs, the kezazah ceremony. A son who had shamed his father and squandered his inheritance among strangers did not walk back into open arms. He walked into a reckoning — the community’s judgment, made public and final. The verdict: cut off permanently, released back to the famine.

Or in the best, unlikely case, the prodigal would work as a hired servant to earn his way back. However, Bailey says that the prodigal would likely become as his older brother — bitter. No restored relationship with the father.

But the father did not run to a category. He ran to a son — reaching him before either could speak, and kissing him again and again.

Worth — shown. Before a word.

Now remember who was listening. The Pharisees had been grumbling: this man receives sinners and eats with them. They carried a picture of God — one who guards His holiness by keeping the unclean out, who waits for the worthless to earn their way back and purges the ones who can’t. So Jesus told a story in which God does the opposite of everything that picture demanded. The law said purge him. The village said cut him off. His own heart said no longer worthy. And the running Father overruled every court that had ever convicted him.

Then Jesus turned to the other son — arms folded, years of service, no idea of the father’s heart. The Pharisee in the parable. The father went out to him too. He did not call him “servant.” He called him teknon — child. The tender word. And left the door standing open.

Worth — spoken. In a name.

This is the correction Jesus came to make: not a new God, but the God who had said it all along, through Hosea, centuries before — I desire hesed, not sacrifice. The God of the Law and the God on the road are one God, and what He has always wanted is not your performance but your homecoming. He shows it by running to the lost. He speaks it over the dutiful. God shows hesed; Jesus shows hesed — telling the story, and sitting down to eat with the very sinners the Pharisees wanted purged.

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Explore the parable: The Younger Son · The Older Son · The Father · The Lost Sheep · The Lost Coin