Matthew 23:11
But he that is greatest among you shall be your servant.
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EXPOSITORY (ENGLISH BIBLE)
(11) He that is greatest among you.—Literally, the greater of you. The words admit of a two-fold meaning. Either (1), as in Mark 9:35, they assert a law of retribution—the man who seeks to be greatest shall be the servant of all; or (2) they point out the other law, of which our Lord’s own life was the highest illustration—that he who is really greatest will show his greatness, not in asserting it, but in a life of ministration. The latter interpretation seems to give on the whole the best meaning.

Matthew 23:11-12. But he that is greatest among you, &c. — If any one among you would in reality be greater than another, let him be the more condescending, kind, and ready cheerfully to serve others in love. The words may either imply, 1st, a promise that such should be accounted greatest, and stand highest in the favour of God, who should be most humble, submissive, and serviceable: or, 2d, a precept enjoining the person who should be advanced to any place of dignity, trust, or honour in the church, to consider himself as peculiarly called thereby, not to be a lord, but a minister, and to serve others in love. Thus Paul, who knew his privilege as well as duty, though free from all, yet made himself servant of all, 1 Corinthians 9:19. And our Lord frequently pressed it upon his disciples to be humble and self-denying, mild and condescending, and to abound in all the offices of Christian love, though mean, and to the meanest; and of this he set a continual example. Whosoever shall exalt himself, shall be humbled, &c. — It is observable that no one sentence of our Lord’s is so often repeated as this: it occurs with scarcely any variation at least ten times in the evangelists.23:1-12 The scribes and Pharisees explained the law of Moses, and enforced obedience to it. They are charged with hypocrisy in religion. We can only judge according to outward appearance; but God searches the heart. They made phylacteries. These were scrolls of paper or parchment, wherein were written four paragraphs of the law, to be worn on their foreheads and left arms, Ex 13:2-10; 13:11-16; De 6:4-9; 11:13-21. They made these phylacteries broad, that they might be thought more zealous for the law than others. God appointed the Jews to make fringes upon their garments, Nu 15:38, to remind them of their being a peculiar people; but the Pharisees made them larger than common, as if they were thereby more religious than others. Pride was the darling, reigning sin of the Pharisees, the sin that most easily beset them, and which our Lord Jesus takes all occasions to speak against. For him that is taught in the word to give respect to him that teaches, is commendable; but for him that teaches, to demand it, to be puffed up with it, is sinful. How much is all this against the spirit of Christianity! The consistent disciple of Christ is pained by being put into chief places. But who that looks around on the visible church, would think this was the spirit required? It is plain that some measure of this antichristian spirit prevails in every religious society, and in every one of our hearts.See the notes at Matthew 20:26.

He that shall humble himself ... - God will exalt or honor him that is humble, and that seeks a lowly place among people. That is true religion, and God will reward it.

11. But he that is greatest among you shall be your servant—This plainly means, "shall show that he is so by becoming your servant"; as in Mt 20:27, compared with Mr 10:44. See Poole on "Matthew 23:12". But he that is greatest among you,.... Either who really is so, having more grace, and greater gifts bestowed upon him, than others; which doubtless was the case of some of the disciples, or who desired to be the greatest, was ambitious of, and affected a superiority over others, and to be in the highest post and place, as it is certain some of them did. This was what they were often contending about among themselves, who should be greatest: and Christ here seems to have regard to that vain spirit, which appeared among them; and his view is, to check and restrain it: "shall be your servant"; or "let him be your servant". Service is the way to honour; he that would be most esteemed ought to do the most work; and the man that has the most grace, and the greatest gifts, ought to employ them for the use and benefit of others; See Gill on Matthew 20:27. But he that is greatest among you shall be your servant.
EXEGETICAL (ORIGINAL LANGUAGES)
Matthew 23:11-12, epeat in substance the teaching of Matthew 20:26 : Matthew 18:4; worth repeating and by no means out of place here.11. Cp. ch. Matthew 20:26-27.

Seven woes denounced against the Scribes and Pharisees. 13–36.Matthew 23:11. Ὁ δὲ μείζων, but he that is greatest) i.e. he who wishes to be the greatest (corresponding with the Hebrew רב[992]); cf. ch. Matthew 20:26.

[992] “רַכ … 2. great … specially (a) i.q. powerful, Psalm 48:3; Isaiah 63:1. Pl. רַבִּים the mighty, Job 35:9; Isaiah 53:12.—(b) elder, Genesis 25:23. Pl. רַבִּים the old, Job 32:9.—(c) subst. a great man, leader, i.q. שַׂר, especially in the later Hebrew …—(d) a master, one who is skilled in any art, skilful, Proverbs 26:10. Compare Talmud. רַב doctor, excellent teacher.”—Gesenius. Bengel evidently intends to refer the reader to Rabbi in verse 7, on which Wordsworth says:—“ῥαββί] רַבִּי, My Master. Rabbi, from root רַב, rab = great; as Magister from magnus, μέγας.—(I. B.)Verse 11. - But he that is greatest...your servant; διάκονος: minister (see Matthew 20:26, 27). It was there said to the apostles alone; here it is spoken more publicly to emphasize the contrast between Christian humility and Pharisaical pride and vanity.
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