Luke 7:43
Simon answered and said, I suppose that he, to whom he forgave most. And he said unto him, Thou hast rightly judged.
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EXPOSITORY (ENGLISH BIBLE)
(43) I suppose that he. . . .—The same word occurs in the same sense as Acts 2:15. As used here, it seems to carry with it a tone partly of indifference, partly of uneasiness and perplexity as to what the drift of the parable might be.

7:36-50 None can truly perceive how precious Christ is, and the glory of the gospel, except the broken-hearted. But while they feel they cannot enough express self-abhorrence on account of sin, and admiration of his mercy, the self-sufficient will be disgusted, because the gospel encourages such repenting sinners. The Pharisee, instead of rejoicing in the tokens of the woman's repentance, confined his thoughts to her former bad character. But without free forgiveness none of us can escape the wrath to come; this our gracious Saviour has purchased with his blood, that he may freely bestow it on every one that believes in him. Christ, by a parable, forced Simon to acknowledge that the greater sinner this woman had been, the greater love she ought to show to Him when her sins were pardoned. Learn here, that sin is a debt; and all are sinners, are debtors to Almighty God. Some sinners are greater debtors; but whether our debt be more or less, it is more than we are able to pay. God is ready to forgive; and his Son having purchased pardon for those who believe in him, his gospel promises it to them, and his Spirit seals it to repenting sinners, and gives them the comfort. Let us keep far from the proud spirit of the Pharisee, simply depending upon and rejoicing in Christ alone, and so be prepared to obey him more zealously, and more strongly to recommend him unto all around us. The more we express our sorrow for sin, and our love to Christ, the clearer evidence we have of the forgiveness of our sins. What a wonderful change does grace make upon a sinner's heart and life, as well as upon his state before God, by the full remission of all his sins through faith in the Lord Jesus!I suppose ... - He saw not "the point" of our Lord's parable. By thus saying, therefore, he condemned himself, and prepared the way for our Lord's reproof. 40-43. Like Nathan with David, our Lord conceals His home thrust under the veil of a parable, and makes His host himself pronounce upon the case. The two debtors are the woman and Simon; the criminality of the one was ten times that of the other (in the proportion of "five hundred" to "fifty"); but both being equally insolvent, both are with equal frankness forgiven; and Simon is made to own that the greatest debtor to forgiving mercy will cling to her Divine Benefactor with the deepest gratitude. Does our Lord then admit that Simon was a forgiving man? Let us see. See Poole on "Luke 7:40"

Simon answered and said,.... Very readily, without any hesitation, not being aware of the application of it, to the instance he had been pondering in his mind:

I suppose, that he to whom he forgave most; it was his opinion, and to him a plain case, that he that owed the largest debt, and that being forgiven him fully, and freely, as he was under the greatest obligation, so as he ought, he would show the greatest love and affection to his kind and gracious creditor:

and he said unto him; that is, Jesus said, as the Syriac and Persic versions express it:

thou hast rightly judged; this is a right and true judgment of the case; it is according to the nature and truth of things, and what is obvious and clear at first sight, and which every one must agree to.

Simon answered and said, I suppose that he, to whom he forgave most. And he said unto him, Thou hast rightly judged.
EXEGETICAL (ORIGINAL LANGUAGES)
43. I suppose] ‘I imagine;’ ‘I presume.’ The original word has a shade of supercilious irony (comp. Acts 2:15), as though Simon thought the question very trivial, and never dreamt that it could have any bearing on himself.

rightly] There is a touch of gentle sarcasm in the use of this word, which involves Simon’s self-condemnation. It is the word so often adopted by Socrates as one of his implements of dialectic irony.

Luke 7:43. Ὀρθῶς) כן, LXX. ὀρθῶς.—ἔκρινας, thou hast judged) a judgment which goes against thine own self; Luke 7:47.

Verse 43. - Thou hast rightly judged. "Come, now, I will show thee what I meant by my little story, in thine answer. Thou hast judged thyself. Thou art the man with the little debt of sin, as thou thinkest, and the little love given in return for the cancelled debt; for see how thou hast treated me thy Guest, and how she has made up for thy lack of friendship and courtesy." The following contrasts are adduced by the Master: "Thou didst not provide me with that which is so usual to offer guests - I entered into thine house, thou gavest me no water for my feet" (in those hot dusty countries, after walking, water to wash the feet was scarcely a luxury, it was rather a necessity); "in thy house the only water which has touched my feet was the warm rain of this sad woman's tears." Luke 7:43I suppose (ὑπολαμβάνω)

The verb literally means to take up by getting under. It might be rendered, accordingly, I take it.

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