Confessions of an Older Brother

“When Judas, who had betrayed him, saw that Jesus was condemned, he was seized with remorse and returned the thirty pieces of silver to the chief priests and the elders. “I have sinned,” he said, “for I have betrayed innocent blood.” “What is that to us?” they replied. “That’s your responsibility.” So Judas threw the money into the temple and left. Then he went away and hanged himself.” Matthew 27:3-5 NIV

I don’t know of any three verses that create a more vivid tale of betrayal and the pangs of conscience that follow. It says Judas is “seized with remorse”. In other versions that phrase is translated as ”repented himself”. It means, “to care afterwards. i.e. regret”. Judas had a heart of stone: numb and leprous that had been groomed through years of duplicity and theft (John 12:6) – he was just the open door Satan needed (Luke 22:3, Eph. 4:25-28). But now, in a moment, his heart becomes flesh, full of nerve endings: sensitive, and he abhors what he has done. He has hurt someone innocent. Someone who didn’t deserve this. In one lucid instant it all hits him, “What have I done?”

I can imagine him standing in front of the the chief priests and elders with desperate manic urgency trying to recant his actions. He’s changed his mind. But of course, life doesn’t allow retractions. There are no redos. And now, guilt would be the greatest punishment of all. But to Judas, that was not an option. There was just no way.

Overcome, I can see his shaking hands throwing the rope over the branch, sweat and tears soaking his face; his chest heaving with anguish. Then, all that is left of our guilty betrayer is a picture of two dangling feet hanging from a tree.

To me, he is the ultimate depiction of a tormented sinner. I have needed to understand this lesson more than you could probably imagine. In the past, my worldview has narrowly been organized into two archetypes: villains and victims. The term, “tormented sinner” would have had no place in my consideration; it would have been an oxymoron. Only victims are tormented. Villains selfishly reek havoc and then walk away unscathed. My journey through this area of growth has inspired this blog post.

Confessions of an Older Brother

I sat at a cold concrete table watching her.  It was your average two year old birthday party at Mission Bay.  Wind, cake, playgrounds, children running wild, parents chatting, and a few random kites flying in the breeze.  A diaper wearing child seemed to be up way past his nap time, and as he blubbered at the top of his lungs, his mother caught my eye.  She silently stood directly in front of him as he demonstrated for her the full range of his emotions.  It started as a typical toddler meltdown but when that yielded no results, his voice got louder, his body grew more limp, and his knees gave out.  He was now sprawled completely flat on the pavement, quickly fading into a puddle of tears and exhaustion.  His mother stared at him blankly.  His tears were in vain as his dramatic presentation clearly did nothing for her.  She was unmoved.

Now contrast her lack of compassion to another experience.  One night I was chatting with my Aunt Robin as she stirred some spaghetti sauce at the stove and I mentioned an article I had read about a child bride and the sad fate that had befallen her.  Robin stopped stirring, put her hand against the cabinet and took some slow heavy breaths.  I could see the visual horrors pass through her mind as she imagined what I had just described.  Overwhelmed, salty droplets began running down her cheeks and choking up, she struggled to verbalize her grief to me.  Robin was moved with compassion.

For months I had chewed and chewed on the expression “moved with compassion”.  The Holy Spirit had illuminated it for me in my Bible readings and now He had brought it to life.  I could see it clearly: one heart stirred while the other was indifferent.  What accounts for these polar reactions?  It comes down to one little word: pity.  That is where we will set up our spiritual tents today.

First we’ll be starting in Matthew and looking at the parable of The Unforgiving Servant.  A servant was in debt to his master several millions of dollars.  When you consider the going rate for a day’s work, it is estimated that it would have taken him over 190,000 years to pay off his outstanding balance.  I think it’s fair to say this man was not a one-time borrower.  This was not one dreadful compulsive decision made in haste; it was who he had become.  Day after day, choice after choice, he had sunk deeper and deeper into financial slavery.  “Deadbeat” had become his defining characteristic.  And today was the day of reckoning; time to “settle accounts”.

Now the man had to look, really look, at what he had done, and it was bleak.  Obviously unable to repay, he would be thrown into slavery and any of his belongings would be sold.  His wife and children would be thrown into slavery for his poor judgement as well.  Everyone he loved would be going down with him.  Everyone would suffer.  Everyone would pay.  All eyes would be on him and his failure: failure to control himself, failure to provide, failure to protect, failure to be everything he was supposed to be to them: husband and father.  In this moment, his world comes crashing down around him: a jolting dose of reality.

Broken, he falls to the ground prostrate and throws up a “hail Mary”: making an absurd, empty promise to pay back the money if he would just be given more time.

Amazingly, unlike the toddler’s mom described earlier, his master did not stare blankly, unmoved and unimpressed.  Instead, like my Aunt Robin, the master’s heart was moved.

It says,

“Then the master of that servant was moved with compassion, released him, and forgave him the debt.”

This small contemptible man was pathetic and desperate.


So the master, hearing his plea, forgives him everything.  Later claiming,

“…I had pity on you?”  Matthew 18:33

And there it is: pity.

The other story of a man “moved to compassion” is in Luke 15.  It was the father of the Older Brother and The Prodigal Son.  The younger brother had asked for his portion of their inheritance early…like really early.  Then, lacking any restraint or sense of propriety, left his father and older brother behind and squandered all of his inheritance on lewd living – earning himself the epithet, “The Prodigal Son”.  Meanwhile, back at the farm, The Older Brother chose to stay home and continue on as appropriate and planned.

If you know the story, then you know once the money was gone, the younger son eventually came crawling back home to his father.  And when he does, it says of the father,

“…his father saw him, and was moved with compassion…” Luke 15:20 ASV

After a tearful reunion, the father throws a party to celebrate his younger son’s safe return.

Everyone is happy. (Luke 15:24)  Everyone except the older brother. (Luke 15:28)

Here is where I come in.  In the prodigal son story, I’m the Older Brother.  My emotions definitely fall on the “Cry Me a River” side of the ledger; I feel no pity for the saved and wayward and I am not “moved with compassion” when they return.  I am particularly harsh if others have been hurt by their idiocracy (which is always the case since no one can sin in a vacuum).  So I’m harsh every time.  I’m much like the mother at the beginning of this post standing in front of her crying child.  I look and I stare, but I am unmoved.  And if I’m being honest, I’ve always felt the older brother has some legit points.

Don’t get me wrong: I’m not talking about the unsaved coming to Christ.  The world is the world and they are going to act like the world.  I have no expectations for them.  So when a sinner becomes saved, I genuinely rejoice.  I’m talking about those that know better: Christians that have walked with the Lord.  I’m talking about a Christian that has been presumptuous and defiant, jumping headlong into lawlessness.  I’m not saying that I’ve never gone through dry spells or a season of less than savory choices, but in general, I’ve remained a Christian and for those on the outside looking in, I’ve always been considered a walking Christian (even though there are several unflattering pictures roaming around this world somewhere).  So the hard part for us older brothers is that the Prodigal Son, is a son;  he isn’t an outsider.  We get why the heathens do what they do, but a son?  He knows better and did it anyway.  This is just audacity, not ignorance.  You were insulting, prideful, stupid and now you’ve “come to your senses”.  Well, la de da.  Am I supposed to do cartwheels?


That’s gonna happen.

Older Brothers believe that while we stayed, worked the field (Luke 15:25) and served (Luke 15:29): leading the measured life, Prodigals went out and had fun.

“Older Brother Syndrome” might also be called “The Little Red Hen Syndrome”.  “I worked, The Prodigal played, and now we get the same results?  Just forget the whole thing ever happened?  So and so got their act together (like I’ve done the whole time) and is ready to sit at the grown up table with the rest of us and I’m supposed to swoon?  While he made his proverbial nightlife bed, I took a multivitamin and unmade my literal bed to retire early so I could get a jump on tomorrow’s work day.  He says, ‘never mind,’ and that clears it all up for you?  I’ve got an idea, how about we just rub his nose in it, cull the heard and send him packing.”

The Lord has shown me that the bedrock under all this sarcasm is the insidious lie that lives buried in my black little heart.  Something I would never admit out loud (but feel strangely comfortable admitting to the world online).  It tells me that sin holds a thrill I have missed out on out of conscience, obligation, and right living; righteousness makes me miss out.  Older Brothers (at least my version of him) think the Prodigal son had his cake and gets to eat it too.  This is where my sense of justice boils over.  “You don’t get to run amuck and then come home and have it all forgiven.  You made your bed now lay in it.  You don’t think I would have had fun eating cake?  I sacrificed.”

And here is why it is a lie: the prodigal son was not coming back on a parade float.

If you read both stories you will see the erring parties (the servant and the son) don’t even ask for forgiveness – they ask for leniency.  Forgiveness isn’t even on the radar – that would be preposterous.  Their sin is heinous and they know it (Luke 15:18).   Being crushed under its weight, all they can hope for is some relief: some mercy.

A repentant sinner is not to be envied, they are to be pitied (Matt. 18:33).  Because a repentant sinner is suffering.  One of the definitions for “pity” says, “to help the afflicted, to bring help to the wretched”.  A sinner is a self-afflicted wretch, but afflicted none the less.

Prodigals make their own beds (which is where I trip up) but it doesn’t mean it feels any better to lay in it.

“…if I make my bed in hell,.…”  Ps. 139:8 KJV

You’re still in hell.

Older Brother’s need to take hold of this truth with both hands.

The veil sin carried with it has been lifted, the sin-fog has cleared and the horror of The Prodigal’s choices is “ever before them”.

“For I recognize my rebellion; it haunts me day and night.”  Psalm 51:3 NLT

Like a punch to the gut, they’re left to look out at the carnage of a tattered life.   They’re left shattered and demoralized, begging God for any break they can get – anything at all.  Because all “knowing better” means is that you know you’re guilty.  (Luke 15:17-21)

Older Brothers (perhaps blinded by their own sin-veil) don’t see the whole story.

If we take a closer look back at The Prodigal Son’s journey, right about the time his money dried up, so did the sky: famine hit.  Penniless and friendless (when the money is gone, the “friends” go with it) he, in desperation, finds a job feeding pigs.  Now he is not only desperate but he is humiliated as well.  And this particular brand of humiliation brought with it a unique sense of worthlessness.  Pigs are of some value and so they are fed and fattened, but he, of no worth to anyone, was left to starve; pigs meant more to this world than he did.

“And he (The Prodigal Son) would gladly have filled his stomach with the pods that the swine ate, and no one gave him anything.”  Luke 15:16 NKJV

As far as he could tell, he would die unmissed and unwanted.  He had been “the man” not that long ago, with money, wanton women and friends surrounding him, but that was all gone now and he is learning a very painful lesson: falling feels a lot like flying until you hit the ground.  Sitting in the pig pen, he immediately perceives that even his father’s lowest servants are better off than he is.  So he resolutely leaves the world behind, severing all attachments to it and heads straight home.

He straggles up the road, hungry, tired from the long journey home (ironically that same determined journey away from the Father is just a long way home now), and groveling.  Covered with dirt on the outside and filth on the inside, he practices his pitch. (Luke 15:18)

A true prodigal (as opposed to those who are back in the fold on the outside but unrepentant on the inside) is contrite and does not see their time in the world the way the older brother may see it.  What was effortless and fun at one time has become repugnant to the thought.  He is mortified and hurting as all his exciting times have turned to ash in his hands.  His public fall from grace is an embarrassment to the family and an embarrassment to himself.  He is a colossal disappointment.

On top of all that, his inheritance is gone and we don’t read in the story that he ever gets a second helping.  In this life, even forgiven and loved people have consequences that last till death.  The Prodigal had made a bad trade.  He handed in future security and comfort for momentary pleasure.  That equation works out the same every time: loss.  Nonsense is expensive.

To be the older brother (imagine the bright neon arrow pointing down at my head right now) shows an incredible lack of wisdom.  We seem to miss a very simple truth: all sin is cursed.(Rom. 6:23, Rom. 6:21, James 1:15)

As an older brother, there is nothing to envy about those that have tasted the world.  If someone is truly repentant, the truth is, they’d take it all back if they could.  They wish they’d stayed.

Because the fact is, you cannot sin and not hurt yourself.  Sin is self-harm because our flesh is a Judas and it’s trying to kill us.  The Bible speaks so clearly on the subject.

“Can a man scoop fire into his lap without his clothes being burned?”  Proverbs 6:27

“…they suffered within themselves the penalty they deserved.”  Romans 1:27 NLT

“But she that liveth in pleasure is dead while she liveth.” I Timothy 5:6 ASV

There is a law of sin and it is as dependable as the law of gravity: you can test it, but it works every. Single. Time.

An OB doesn’t trust this is true.  We may admit it mentally, but our heart has rejected its veracity.  If you think someone has not suffered for their sin, it is to call God a liar.   That means that long before I give my younger brother a once over, I have a major “plank” (Matt. 7:1-5) to repent of – the sin of unbelief.  I am not as squeaky clean as I project.

Of course not! Even if everyone else is a liar, God is true. As the Scriptures say about him, “You will be proved right in what you say, and you will win your case in court.”  Romans 3:4 NLT

Once I’ve repented, I believe the self-righteousness obstructing my view will dissipate and the natural response will be stirrings of sorrow, not criticism for the returning brother; we would genuinely have pity and be “moved to compassion”.

So if there are any other “Older Brothers” reading this, let’s be happy we stayed close to the Father – an honest days work for an honest days pay.

“I know that nothing is better for them than to rejoice, and to do good in their lives, and also that every man should eat and drink and enjoy the good of all his labor – it is the gift of God.”  Ecclesiastes 3:12-13 NKJV

Fellow O.B.s, with our inheritance intact, our honor preserved, and our memories unskewed, we have always been living the good life.  The Prodigal went from starving (pig pen) to full (fatted calf), but we’ve always been full.  Isn’t that essentially what the father says to the Older Brother?

“Son, you are always with me, and all that I have is yours.”  Luke 15:31 NKJV

“Do you want a party? Nothing has ever stopped you from having a party.  Have a party.” (my paraphrase)

We’ve always had the best.  The “fatted calf” has always been available and ready should we have wanted it, and all the while we’ve never suffered through starvation, squalor, humiliation, wasted time or regret of our own makings.

If a prodigal should “come to their senses” lets rejoice that they came back to join us again and rejoice that we’ve never left.  We’ve never suffered the loss the younger brother did and we’ve never slept in a pig pen.  Praise God.

“He (Satan) will gladly oblige by taking the inch you give him and running with it—not for miles, but until you’re dead, destroyed, or pleading for mercy. For your sake I hope it’s God’s mercy for which you plead.”  Rebecca Halton, Words from the Other Woman: The true account of a redeemed adulteress.


  1. Jena…your words are inspiring. Thank you for letting us in.


      Hey Caroline, Thanks so much for the encouragement. I’m always so excited to hear when it resonates with someone.

  2. Well said, friend! I have often felt like the older brother myself, then chastise myself for thinking I’m the older brother instead of the prodigal–how conceited of me….anyhow, I love your spin on this story!

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