Seeking Sinking Simon

That Thing That Dad’s Do.
September 17, 2018
The Pastor And You
October 3, 2018

Seeking Sinking Simon:

The Greatest Debtor of All

By Pastor Vinnie


Do you ever feel like no matter what you did there would always be someone there to criticize you? I am pretty sure Jesus felt this same way, at times.

After all, He had just healed a man with a withered hand, healed the Centurion’s servant, and raised the son of Widow Nain from the dead and yet still questions abound about Him! Even by the very disciples of John the Baptist. The One who said of Jesus, “Behold the Lamb of God” now had questions. Was he (John) giving up his life for the right and real Messiah?

A day like that in ministry would be enough to make you want to go home and forget about it all for a while, with a good book and a nap! But no, that is not the way of Jesus. That is not the mission of Jesus, and that is not the method of Jesus.

He would not spend a nice quiet evening at home forgetting His troubles. Instead, He was going to go head first into the den of His enemies!

Simon, a Pharisee, had invited Jesus to his home for a meal. This was a make it or break it moment of the Public Ministry of Jesus that was in its final quarter before the Cross. Simon was fixated on Jesus after Jesus healed him. He likely threw this whole dinner party to get the other Pharisees to see they should accept Jesus into their inner circle. Simon knew, if ever the elite were going to accept Jesus, it was now! If this went well, this dinner party could save Jesus from the evil plotting of the Pharisees. However, Jesus and the Pharisees were not exactly known for being on friendly terms and having dinner parties together!

The Pharisees, along with the priests and scribes, saw Jesus as a direct threat to their authority and influence over the people. They had, on several occasions, already co-plotted together to have Jesus killed! And now, Jesus goes to one of their houses for dinner? Why would He do that? Why would He put himself in harm’s way, at risk, at ridicule? What good could come out of it? Why even bother? Why not just go home, especially after the day he had been having?

Simple: Jesus loved Simon and wanted, at all costs — even to Himself, to save Simon. Simon also wanted to save Jesus, from the fate of the plans of the elite leadership. Jesus, was willing to give everything to save Simon, but Simon only had a party to provide Jesus with, and even that Simon feared was going too far for this own good.

As I pondered this, I could not help but think: How much do I love my enemies? Enough to die for them? Honestly, I’d rarely even throw them a party let alone die for them. Jesus loves Simon, and Jesus loves every Pharisee at that party. Jesus seeks to save even those who are His enemies.

How much do you love those who seek to kill you? You see this is what determines how much we are really like Jesus.

Simon had already been healed of leprosy, yet he still did not fully believe who Jesus was. He just wanted to bring Jesus into the inner circle. Jesus had other plans. This is the context in which we find Jesus going to Simon’s house; seeking to save that which is lost; namely Simon.

One of the Pharisees asked him to eat with him, and he went into the Pharisee’s house and took his place at the table. And behold, a woman of the city, who was a sinner, when she learned that he was reclining at table in the Pharisee’s house, brought an alabaster flask of ointment, and standing behind him at his feet, weeping, she began to wet his feet with her tears and wiped them with the hair of her head and kissed his feet and anointed them with the ointment. Luke 7:36-38

There is Jesus at the house of Simon, the Pharisee, — the former leper, now healed. All the other Pharisees are present, and I am ever so sure they stand ready to judge Him and condemn Him on any perceived wrong move He makes. Suddenly their attention is taken off Jesus and onto a woman who barges into Simon’s house.

Who is this Woman?! While the other Gospel writers may give us clues to the matter, Luke tells us exactly what we need to understand about her. She is a Sinner. Luke uses that word on purpose. She is one who is defined by her sin. No one can look past it. It is all she is to them.

Luke, while avoiding her name tells us exactly what is in everyone’s mind when she walks in that room. She is impure, dirty, unworthy. And there is no place for an immoral woman at a Pharisee’s house in the middle of his dinner party.

Can you imagine what it took for her to walk into that room?

Imagine the stares, finger pointing, sneers, and snickering. I can almost hear the off-putting, snide remarks, and dirty jokes being made about her in the back corner of the room. Imagine the humiliation she faced walking into that room. Imagine, if you will, if you can, she has been impure with some, if not many, of these very men in secret.

And yet notice she pushes through that crowd of high ranking officials, important Pharisees, and other dignitaries. Why? Why does she subject herself to such public embarrassment and ridicule? Simple: To cast herself at the feet of Jesus!

What are we willing to give up just to be with Jesus? Just to cast yourself at the feet of Jesus? She couldn’t care less what people thought of her, as long as she could be with her dear savior if even only His feet? –Oh that we all would have the attitude of this one who is simply called “Sinner” by Luke!

It is while she is sitting there at the feet of Jesus, anointing them with oil and washing them with her hair and tears that an evil thought rises in Simon’s mind…

“If this man were a prophet, he would have known who and what sort of woman this is who is touching him, for she is a sinner.” Luke 7:39

There is that dirty word again… She is a Sinner.

Yet we cannot fail to notice that although Simon is indeed judging this woman, he is at the same time, at least somewhat it appears, willing to consider if Jesus was a prophet. Could it be that even Simon is not beyond a chance of redemption?

Could it be that Jesus, is not there to save the woman at all? After all, she enters the room already repentant. But it is Simon who is still in need of redemption, and it is Simon’s house Jesus has come to, and it is to Simon now, not the woman, who Jesus will turn His attention, and it Simon’s mind Jesus now reads.

Notice the interaction between Simon and Jesus in verse 40.

And Jesus answering said to him, “Simon, I have something to say to you.” And he answered, “Say it, Teacher.”

I love this. Verse 39 clearly states Simon had made his comment in his mind, he “said it to himself” and yet Jesus not only reads Simon’s mind but he calls him into question out loud! Again notice, who does Jesus call attention to what He is about to say? Not the woman, but Simon! And to Simon’s credit, he is still ever willing to listen, even after Jesus let the woman touch Him. Simon says, “Say it, Teacher.”

Then Jesus gives this remarkable yet simple parable:

“A certain moneylender had two debtors. One owed five hundred denarii, and the other fifty. When they could not pay, he canceled the debt of both. Now which of them will love him more?” Luke 7:41-41

Notice both debtors owe money. How much it does not matter. Yes, it is true the values vary hugely, but the point is they both owe the money, and both cannot pay. The fate that would await debtors who cannot pay is not a great fate. All they owned would be taken and sold to make collection and they would then be imprisoned until the remainder could be furnished.

And it is in here, in this condition we not only find the condition of both Simon and the Woman, but we also see the state of all humankind before God.

  • All are fallen

  • All are sinners

  • All unable to help themselves

  • All are doomed to damnation

  • All come up short in the final calculation of debt.

“None is righteous, no, not one; no one understands; no one seeks for God. All have turned aside; together they have become worthless; no one does good, not even one.” Romans 3:10-12

We, like both Simon and the Woman, come up short in our own righteousness. If we, like the debtors, do not have our debts canceled by the moneylender (God) we would have no hope.

It is in the Moneylender we see the love of God for the sinner. It is in the Moneylender we know the love of Jesus, even for Simon. Jesus came to this dinner party, not for worldly esteem, not for pride, not to win the Pharisees to His side, but He came to fulfill His mission and to save that which was lost. He came to rescue His “Sinking Simon.”

The Moneylender cares nothing for your debt, the kind of debt, how you incurred the debt, the amount of debt, the Moneylender cares only of one thing: will you let him pay your debt and be free?   It is this thought Jesus seeks to cement in the mind of Simon.

Simon answered, “The one, I suppose, for whom he canceled the larger debt.” And he said to him, “You have judged rightly.” Luke 7:43

Herein lays the truth of the Parable and the heart of what Jesus wants Simon to understand.

The larger your debt, the more forgiving of the debt should bring forth a wellspring of loved- based gratitude and service. Not that we could repay what we have been forgiven, because the point of the parable is we can never repay our debt, but rather now having been set free for the debt we are now free to serve in love, not duty.

Simon had been a leper. And he had been healed by God. We have no word of certainty from the Bible if Jesus did the healing or if God used another method, but God healed Simon. And in the Jewish mindset being healed by God of such a scourge was to be forgiven of all your sins. Where was the love that should have overflowed now from Simon’s heart? Where is the gratitude for what God has done for him that should awaken the great compassion of God in the very heart of this stone cold Pharisee? This is the issue, Jesus has come to address.

Then, turning toward the woman, he said to Simon, “Do you see this woman? I entered your house; you gave me no water for my feet, but she has wet my feet with her tears and wiped them with her hair. Luke 7:44

We must not get bogged down in the familiarity of this famous passage and miss, exegetically, what is really going on. Notice in verse 44. Who is Jesus talking too? Simon or the Woman?

SIMON! But who is Jesus looking at? The WOMAN!

And with that brief action, Jesus turns the context of this parable entirely around. He sets the whole parable upside down on Simon’s head. It is not the woman who is the greater sinner; it is SIMON!

You see Simon is sure this woman is a greater sinner than him. But Jesus looks to her to be the example to Simon while confronting Simon as if he is the bigger sinner.

Simon is the master debtor! She may be a sinner, but she is penitent. Simon is a sinner, and he is sinking fast. He is Sinking Simon. Simon was the one who was forgiven the most and healed of his affliction. Simon lacked any true repentance, and so Jesus uses this Woman to show Simon what forgiveness and gratitude look like in salvation!

Jesus talks to Simon is verse 44 but looks to the Woman. “Do you see this Woman” … This woman –all her deeds and expressions of love, and sacrifice is what love and forgiveness look like. It is what the fruit of salvation looks like.

But Simon, you had none of that for me!

Therefore, I tell you, her sins, which are many, are forgiven—for she loved much. But he who is forgiven little, loves little.” Luke 7:47

Yes, the woman was a great sinner. But are we not all great sinners? The truth of the matter is she is forgiven much, not because she had the most sins, and Simon was forgiven less for having the less sins! Instead she, unlike Simon, was willing to see her sins for what they are, and throw herself at the feet of Jesus and receive much forgiveness while Simon, on the other hand, would not confess his need of Jesus, thus had little he could be forgiven of.

And yet, Simon had the most sin. Why?

He knew more. He was a Pharisee. He had been esteemed in a high position by God. It was not his to judge the woman. As a leader in Israel it should have been his duty to help restore her (as Jesus did) Yet, rather than seek to restore what was lost (like Jesus) Simon showed his lack of gratitude and acceptance of the Savior’s compassion and forgiveness to him by his judgmental, unloving, ungodly response towards the woman. Simon’s lack of understanding of his condition and lack of love for those which are lost caused him, to surpass her in sin, many times over, to become the greatest debtor of all. Simon sits in judgment when his own forgiveness and healing should leave nothing but compassion for other sinners.

My question is this… Which are we? Which am I?

Am I Simon?

Are we the Woman at the feet of Jesus crying out—begging– for the mercies of God?

Are we like Simon, sitting quietly in our pews thinking in our minds sinful and evil thoughts about those around us who are struggling, who need our help, while we ought to be reaching to save? – Remember Jesus reads out thoughts and deals with them publicly.

Do we sit in judgment or tears?

And he said to her, “Your sins are forgiven.” Then those who were at table with him began to say among themselves, “Who is this, who even forgives sins?” And he said to the woman, “Your faith has saved you; go in peace.”   Luke 7: 49-50

Learn the lesson Jesus sought to teach a Sinking Simon. The only way out of the room is to throw yourself at the feet of Jesus, crying for mercy. Only your Faith in the merits of Jesus can save you. The only merit found in Jesus can make you whole. The only merit found in Jesus can send you in peace.

“Go, go in peace.”


Sermon Version


  1. morethanlegs says:

    This blog has a lot of meat in it. As a woman with a disability I’m frequently targeted as the person needing prayer (for healing) People often miss the point God may wants to heal them through their encounter with me.

  2. Love this. Interestingly I also just wrote about this same verse!

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