What does Isaiah 14:29 mean?
ESV: Rejoice not, O Philistia, all of you, that the rod that struck you is broken, for from the serpent’s root will come forth an adder, and its fruit will be a flying fiery serpent.
NIV: Do not rejoice, all you Philistines, that the rod that struck you is broken; from the root of that snake will spring up a viper, its fruit will be a darting, venomous serpent.
NASB: 'Do not rejoice, Philistia, all of you, Because the rod that struck you is broken; For from the serpent’s root a viper will come out, And its fruit will be a winged serpent.
CSB: Don't rejoice, all of you in Philistia, because the rod of the one who struck you is broken. For a viper will come from the root of a snake, and from its egg comes a flying serpent.
NLT: Do not rejoice, you Philistines, that the rod that struck you is broken — that the king who attacked you is dead. For from that snake a more poisonous snake will be born, a fiery serpent to destroy you!
KJV: Rejoice not thou, whole Palestina, because the rod of him that smote thee is broken: for out of the serpent's root shall come forth a cockatrice, and his fruit shall be a fiery flying serpent.
Verse Commentary:
The prophet Isaiah's oracle against the nation of Philistia begins with this verse. He uses strong symbolism to describe the future suffering for the Philistines. This imagery paints a picture revealing the intensity of the concept the prophet is conveying to the reader.

The people of Philistia were longtime adversaries of Israel (Judges 10:7; 1 Samuel 4:1; 7:10; 14:52; 2 Samuel 21:15; 1 Chronicles 10:1). They lived along the Mediterranean coast west of the Dead Sea. The major Philistine cities were Ashdod, Ashkelon, and Gaza. As with all the nations in the region at that time, they had also been oppressed by the Assyrian Empire. Like Judah, they paid tribute to Assyria in a kind of alliance and to keep them from being destroyed.

Around 715 BC, perhaps in the year that King Ahaz of Judah died (Isaiah 14:28), the Philistines and Judah revolted against Assyria. This revolution gained the two nations some temporary independence while the Assyrians were focused elsewhere in their empire. It seems that Isaiah is writing this prophecy following that victory.

Isaiah warns the Philistines not to rejoice that the "rod that struck them is broken." Rods were solid, straight, heavy sticks used as weapons or tools to control animals. They were symbolic of power and authority; most modern commentators say this rod represents Assyria. They say that the "rod" was broken in the sense that the Assyrians had become somewhat weaker for a time.

Symbolically, the broken rod is the root of some kind of serpent tree. This tree produces deadly snakes as its branches and produces flaming, flying snakes as fruit. Some commentators say the "adder branch" was meant to represent the cruel Assyrian king Sargon II. This king was the one who defeated the Philistine city of Ashdod only four years later and made Philistia an official Assyrian province. Sargon was followed as Assyria's king by the even more terrible Sennacherib, who may have been represented by the flying fire serpent.

As with much prophecy, this is a lot of symbolism to untangle. Scholars have offered various other ideas about what it might all might mean. In the end, Isaiah is clearly prophesying that more tough times are coming for Israel's enemies, the Philistines.
Verse Context:
Chapter 14:28–32 contains Isaiah's short oracle from the Lord against Philistia. It is thick with symbolism. But the time of its writing is specific: the year Judah's King Ahaz died, probably 715 BC. Despite the temporary victory over Assyria, Isaiah warns the Philistines not to rejoice. He seems to describe the return of the Assyrians as an "adder branch" that bears fruit in the form of a flying fire serpent. The Lord declares He will kill the root of the Philistines with famine. This prediction would be fulfilled through the Assyrians and Sargon II four years later.
Chapter Summary:
After the oracle against Babylon in the previous chapter, Isaiah briefly describes what will follow for Judah. In compassion, the Lord will choose His people once more. He will return them to their homeland. They will sing a mocking taunt-song against the fallen king of Babylon. Isaiah pronounces oracles from the Lord against Assyria and Philistia. The Lord will break the Assyrians in His land. With heavy symbolism, Isaiah seems to prophecy that the Assyrians will defeat the Philistines with a siege four years before it happens. God's people will find refuge in Zion.
Chapter Context:
Chapter 14 follows the oracle about the destruction of Babylon with a brief encouragement to the people of Judah. The Lord will restore them to the land. They will taunt the fallen Babylonian king, using phrases many also associate with the fall of Satan. Isaiah pronounces oracles from the Lord against Assyria and Philistia. He declares that He will break the Assyrians in His land, freeing His people from their oppression. Philistia will fall at the Lord's hand to a famine inflicted on them by a power from the north. Next, Isaiah's prophecy will turn to Moab.
Book Summary:
Isaiah is among the most important prophetic books in the entire Bible. The first segment details God's impending judgment against ancient peoples for sin and idolatry (Isaiah 1—35). The second part of Isaiah briefly explains a failed assault on Jerusalem during the rule of Hezekiah (Isaiah 36—39). The final chapters predict Israel's rescue from Babylonian captivity (Isaiah 40—48), the promised Messiah (Isaiah 49—57), and the final glory of Jerusalem and God's people (Isaiah 58—66).
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