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Deuteronomy 33:20

Adam Clarke
Bible Commentary

Blessed be he that enlargeth Gad - As deliverance out of distress is termed enlarging, (see Psalm 4:1;), this may refer to God's deliverance of the tribe of Gad out of that distress mentioned Genesis 49:19, and to the enlargement obtained through means of Jephthah, Judges 11:33, and probably also to the victories obtained by Gad and Reuben over the Hagarites, 1 Chronicles 5:18-20.

He dwelleth as a lion - Probably the epithet of lion or lion-like was applied to this tribe from their fierce and warlike disposition. And on this supposition, 1 Chronicles 12:8, will appear to be a sufficient comment: And of the Gadites there were men of might, men of war for the battle, that could handle shield and buckler, whose faces were Like The Faces Of Lions, and were as swift as the roes upon the mountains. Tearing the arm or shoulder with the crown of the head seems simply to mean that no force should be able to prevail over them, or stand against them; as the arm or shoulder signifies dominion, and the crown of the head, sovereign princes.

Albert Barnes
Notes on the Whole Bible

i. e., Blessed be God who shall grant to Gad a spacious territory. Compare the blessing of Shem Genesis 9:26.

With the crown - Rather, yea, the crown. The warlike character of this tribe is shown by their leading the van in the long campaigns of Joshua (compare Joshua 4:12-13; Joshua 22:1-4). Compare also 1 Chronicles 5:18-22; 1 Chronicles 12:8 ff, and the acts of Jehu, the Gadite, in 2 Kings 9; 10.

Matthew Henry
Concise Bible Commentary
The order in which the tribes are here blessed, is not the same as is observed elsewhere. The blessing of Judah may refer to the whole tribe in general, or to David as a type of Christ. Moses largely blesses the tribe of Levi. Acceptance with God is what we should all aim at, and desire, in all our devotions, whether men accept us or not, 2Co 5:9. This prayer is a prophecy, that God will keep up a ministry in his church to the end of time. The tribe of Benjamin had their inheritance close to mount Zion. To be situated near the ordinances, is a precious gift from the Lord, a privilege not to be exchanged for any worldly advantage, or indulgence. We should thankfully receive the earthly blessings sent to us, through the successive seasons. But those good gifts which come down from the Father of lights, through the rising of the Sun of righteousness, and the pouring out of his Spirit like the rain which makes fruitful, are infinitely more precious, as the tokens of his special love. The precious things here prayed for, are figures of spiritual blessing in heavenly things by Christ, the gifts, graces, and comforts of the Spirit. When Moses prays for the good will of Him that dwelt in the bush, he refers to the covenant, on which all our hopes of God's favour must be founded. The providence of God appoints men's habitations, and wisely disposes men to different employments for the public good. Whatever our place and business are, it is our wisdom and duty to apply thereto; and it is happiness to be well pleased therewith. We should not only invite others to the service of God, but abound in it. The blessing of Naphtali. The favour of God is the only favour satisfying to the soul. Those are happy indeed, who have the favour of God; and those shall have it, who reckon that in having it they have enough, and desire no more.