I found some of the events mentioned confusing so I have included a timeline here.
Think backwards! In BC, the bigger the number, the older the date. And be careful, while some dates are fixed, others are best guesses.
Isaiah 22
A prophecy about Jerusalem
1 A prophecy against the Valley of Vision:
It seems that Isaiah was prophesying when the Assyrians first laid siege to Jerusalem in 701 BC, while Hezekiah was king of Judah (2 Kings 18 & 19).
Isaiah 22:15-25 specifically speaks of Shebna and Eliakim who are mentioned in 2 Kings 18:26.
But the prophecy also looks forward to coming sieges when Jerusalem will finally fall (597-586 B C)
Isaiah’s prophecy continues:
What troubles you now, that you have all gone up on the roofs, 2 you town so full of commotion?
There was a panic in the city; the rumour was ‘the Babylonians are coming!’
Verse 2 continues:
‘you city of tumult and revelry’
The people of Jerusalem were actually no better than those of Babylon itself (Isaiah 21:5) when it came to revelry.
The flat roofs of the houses were used as much as the rest of the house, if there was something going on you would immediately go upstairs to see – and call out to your neighbours.
In 605 BC. Babylon had taken over the lands once ruled by Assyria, and Judah stood out as a rebellious state. Nebuchadnezzar attacked and Jehoiakim, king of Judah, became his vassal. After 3 years Jehoiakim rebelled and the end result was in 597 BC, Jerusalem was besieged for the second time. Finally Jehoiakim surrendered and was replaced by Zedekiah – he was installed as Babylon’s vassal for 11 years. At that time Jerusalem was looted and many important people taken into exile (2 Kings 24:10-17.
It was now Zedekiah’s turn to rebel, and as a result in 586 BC Nebuchadnezzar came back and besieged Jerusalem again for the third and final time.
Isaiah’s prophecy continues, but speaking as if the future has already happened
Verse 2 continues:
Your slain were not killed by the sword, nor did they die in battle.
Possibly referring to those who would die of starvation in the siege; or possibly those who had been exiled to Babylon died there.
3 All your leaders have fled together; they have been captured without using the bow.
All you who were caught were taken prisoner together, having fled while the enemy was still far away.
2 Kings 25:1-10 contains a graphic account of what actually happened.
Now it could be Isaiah or it could be the Lord himself who is distressed to see what the disobedience of his people will bring on them.
4 Therefore I said, ‘Turn away from me; let me weep bitterly. Do not try to console me over the destruction of my people.’
5 The Lord, the Lord Almighty, has a day of tumult and trampling and terror in the Valley of Vision, a day of battering down walls and of crying out to the mountains.
6 Elam takes up the quiver, with her charioteers and horses; Kir uncovers the shield.
Again we have ‘a day’ of the Lord when Jerusalem will be totally destroyed. Elam (southwestern Iran), and Kir (possibly east of the Dead Sea) were also prepared to join the battle.
7 Your choicest valleys are full of chariots, and horsemen are posted at the city gates.
8 The Lord stripped away the defences of Judah, and you looked in that day to the weapons in the Palace of the Forest.
9 You saw that the walls of the City of David were broken through in many places; you stored up water in the Lower Pool.
10 You counted the buildings in Jerusalem and tore down houses to strengthen the wall. 11 You built a reservoir between the two walls for the water of the Old Pool, but you did not look to the One who made it, or have regard for the One who planned it long ago.
12 The Lord, the Lord Almighty, called you on that day to weep and to wail, to tear out your hair and put on sackcloth.
It was obvious – the attacking army filled the valleys and surrounded the gates. Frantic attempts were made to withstand the coming terror, but no attempt was made to turn back to God. The Lord called for repentance, but again he was ignored.
13 But see, there is joy and revelry, slaughtering of cattle and killing of sheep, eating of meat and drinking of wine!
‘Let us eat and drink,’ you say, ‘for tomorrow we die!’
14 The Lord Almighty has revealed this in my hearing: ‘Till your dying day this sin will not be atoned for,’ says the Lord, the Lord Almighty.
Many times, the Lord had provided righteous kings to turn his people back to him, but it seemed that the people were intent to live life without him. Even in this time of siege there would be feasting and revelry. The Lord sent many prophets to warn them that there would be a day of reckoning, but they too had been ignored.
The exile would last 70 years - until everyone involved (including Isaiah) had died. Only then would their 'sin be atoned for' and the Lord would provide their salvation through Cyrus the Great of Persia.
15 This is what the Lord, the Lord Almighty, says:
‘Go, say to this steward, to Shebna the palace administrator: 16 what are you doing here and who gave you permission to cut out a grave for yourself here, hewing your grave on the height and chiselling your resting-place in the rock?
Shebna was obviously a very high-ranking official, but even so he had ideas above his station. Lavish tombs were reserved for royalty.
17 ‘Beware, the Lord is about to take firm hold of you and hurl you away, you mighty man.
18 He will roll you up tightly like a ball and throw you into a large country. There you will die and there the chariots you were so proud of will become a disgrace to your master’s house. 19 I will depose you from your office, and you will be ousted from your position.
When destruction comes, there will be no escape – Shebna too will be exiled with all the rest. But for now, (verse 19) he will be demoted to the position of secretary (Isaiah 36:3)
20 ‘In that day I will summon my servant, Eliakim son of Hilkiah. 21 I will clothe him with your robe and fasten your sash around him and hand your authority over to him. He will be a father to those who live in Jerusalem and to the people of Judah. 22 I will place on his shoulder the key to the house of David; what he opens no one can shut, and what he shuts no one can open. 23 I will drive him like a peg into a firm place; he will become a seat of honour for the house of his father. 24 All the glory of his family will hang on him: its offspring and offshoots – all its lesser vessels, from the bowls to all the jars.
Eliakim will be lifted up and will be given all authority. The picture here is a strong peg, hammered into a strong wall, on which all his family will be supported – for now.
25 ‘In that day,’ declares the Lord Almighty, ‘the peg driven into the firm place will give way; it will be sheared off and will fall, and the load hanging on it will be cut down.’ The Lord has spoken.
No-one, however important or self-important will be able to survive the Word of the Lord.
Isaiah 23
1a A prophecy against Tyre:
Tyre had been a major port since before 2000BC. It was built on an island, half a mile from the mainland. Together with its sister port Sidon, they had been conquered several times throughout their history but even if destroyed they were quickly rebuilt – they were too profitable for their new masters. But even while they were under foreign rule they would often rebel.
Wikipedia tells us:
Tyre, Byblos, and Sidon all rebelled against Assyrian rule. In 721 BC, Sargon II besieged Tyre and crushed the rebellion. His successor Sennacherib suppressed further rebellions across the region. During the seventh century BC, Sidon rebelled and was destroyed by Esarhaddon, who enslaved its inhabitants and built a new city on its ruins. By the end of the century, the Assyrians had been weakened by successive revolts, which led to their destruction by the Median Empire. The Babylonians, formerly vassals of the Assyrians, took advantage of the empire's collapse and rebelled, quickly establishing the Neo-Babylonian Empire in its place. Phoenician cities revolted several times throughout the reigns of the first Babylonian King, Nabopolassar (626–605 BC), and his son Nebuchadnezzar II (c. 605–c. 562 BC). In 587 BC Nebuchadnezzar besieged Tyre, which resisted for thirteen years, but ultimately capitulated under "favourable terms"
Tyre was later conquered in 332 BC by Alexander the Great of Greece who built a causeway out to the Island.
Isaiah was probably writing between 740 BC and 686 BC
1b Wail, you ships of Tarshish! For Tyre is destroyed and left without house or harbour.
From the land of Cyprus word has come to them.
2 Be silent, you people of the island and you merchants of Sidon, whom the seafarers have enriched.
3 On the great waters came the grain of the Shihor; the harvest of the Nile was the revenue of Tyre, and she became the market-place of the nations.
‘Ships of Tarshish’ were a class of huge seafaring vessels that had traded for centuries within the Mediterranean Sea and beyond (Even to England – Ezekiel 27:12).
Similar ships also operated from the Red Sea to the west coast of Africa and India. Phoenicians were well-known for their skills in sailing, and also trade. Their merchants had also settled and set up import/export businesses in many foreign port cities.
4 Be ashamed, Sidon, and you fortress of the sea, for the sea has spoken:
‘I have neither been in labour nor given birth; I have neither reared sons nor brought up daughters.’
5 When word comes to Egypt, they will be in anguish at the report from Tyre.
6 Cross over to Tarshish; wail, you people of the island.
7 Is this your city of revelry, the old, old city, whose feet have taken her to settle in far-off lands?
In their culture, childless couples felt ashamed. Here what had been rich and fertile was now to become bleak and barren. The cities that had boasted in their revelry would be a site of mourning.
8 Who planned this against Tyre, the bestower of crowns, whose merchants are princes, whose traders are renowned in the earth?
9 The Lord Almighty planned it, to bring down her pride in all her splendour and to humble all who are renowned on the earth.
How could anyone have foreseen such terrible disaster? Previously several attackers had laid siege to Tyre but as an island trading port it had always sprung up again like a weed where the top had simply been cut off. But now – only one could have planned such devastation – The Lord Almighty.
10 Till your land as they do along the Nile, Daughter Tarshish, for you no longer have a harbour.
11 The Lord has stretched out his hand over the sea and made its kingdoms tremble.
This seems to suggest that there will come a time (probably under the Assyrians 700 BC) when having deported the Phoenician population, they repopulated it with foreigners. No ship-owner would attempt to trade while the land was under the control of Assyria. Besides, those people who had been installed were farmers, not sailors and traders.
He has given an order concerning Phoenicia that her fortresses be destroyed.
12 He said, ‘No more of your revelling, Virgin Daughter Sidon, now crushed!
‘Up, cross over to Cyprus; even there you will find no rest.’
13 Look at the land of the Babylonians, this people that is now of no account!
The Assyrians have made it a place for desert creatures; they raised up their siege towers, they stripped its fortresses bare and turned it into a ruin.
14 Wail, you ships of Tarshish; your fortress is destroyed!
15 At that time Tyre will be forgotten for seventy years, the span of a king’s life. But at the end of these seventy years, it will happen to Tyre as in the song of the prostitute:
16 ‘Take up a harp, walk through the city, you forgotten prostitute;
play the harp well, sing many a song, so that you will be remembered.’
God has spoken. If you don’t believe him, look at Babylon; see how the mighty have fallen. Now their only source of income will be the ignored fields – they had never been worked because there was easy money to be found at the port. But it will only be for a lifetime – until the resurgence of Babylon around 630 BC.
17 At the end of seventy years, the Lord will deal with Tyre. She will return to her lucrative prostitution and will ply her trade with all the kingdoms on the face of the earth. 18 Yet her profit and her earnings will be set apart for the Lord; they will not be stored up or hoarded. Her profits will go to those who live before the Lord, for abundant food and fine clothes.
Now it seems that there will be another change of ownership (Possibly under Cyrus when they helped the rebuilding of the temple in Jerusalem – Ezra 3:7).
But also see Isaiah 60:9. ‘Seventy years’ may be a symbolic number! (see Luke 6:17 and Acts 21:3-4).
