Upsetting the World Dictator: History in HIS Story. Isaiah #6

Jerusalem Under Siege

Inspired by | Isaiah 37 | 2 Kings 19 | 2 Chronicles 32 | Other Historical Sources below |

Welcome back, listeners, to another gripping episode of our series. Today, we’re standing on the edge of a critical moment—a confrontation that could determine the fate of Jerusalem itself. The mighty Assyrian Empire, with its unyielding army, has not taken kindly to resistance, and King Hezekiah’s choice not to surrender has kindled the fierce anger of King Sennacherib. Will Jerusalem stand against the wrath of Assyria, or will faith in the Lord be their salvation? Let’s find out.

The Fury of Sennacherib

Imagine the scene in 701 BC: Sennacherib, King of Assyria, one of the most powerful men in the ancient world, seething with anger in his royal tent. His military conquests stretched across the known world, and yet here was Jerusalem—a small city clinging to hope and refusing to submit.

The Assyrian king’s patience had worn thin. After his messenger, the Rabshakeh, delivered a speech crafted to strike fear and submission into the hearts of the people, Jerusalem remained silent. No surrender. No response. Just the stubborn silence of a city too proud—or too faithful—to bend the knee.

Sennacherib’s fury blazed like wildfire. He could not allow this insult to stand. Gathering his massive army, 185,000 strong, he moved them in formation toward the walls of Jerusalem. It was a show of overwhelming force, the very ground trembling beneath the boots of his soldiers. Siege engines rolled forward. Banners unfurled. The mighty Assyrian army stood at Jerusalem’s walls. It wasn’t just an attack—it was a message: No one defies Sennacherib.

In his tent, Sennacherib sat down to compose one final letter to Hezekiah. His words dripped with scorn and fury, mocking the God of Israel, mocking Hezekiah’s faith, and warning of the destruction that would surely follow. The letter was his final ultimatum: surrender, or face the obliteration of your people, your city, your children.

Hezekiah’s Weakness and Desperation

Inside the walls of Jerusalem, the air was thick with fear. Hezekiah’s failure was known to all— he had once trusted in an alliance with Egypt, despite the warnings. How foolish those alliances seemed now! He could hear Isaiah’s voice in his head: “Woe to those who go down to Egypt for help, and rely on horses, who trust in chariots because they are many…” The words haunted him, a reminder that his past mistakes were now laid bare before his people. Now, here he was, surrounded by the very force Isaiah had said Egypt would never protect him from.

Too weak to act, too burdened with guilt, Hezekiah tore his robes and covered himself in sackcloth, the garment of mourning. He sent his trusted officials to Isaiah with a desperate message, admitting his helplessness:

“This day is a day of trouble, of rebuke, and of disgrace. It is like a woman in labor who is too weak to give birth. The children are ready to be born, but there is no strength to deliver them.” Hezekiah’s leadership, once filled with confidence, was now fraught with guilt and rebuke. He had no illusions about his own strength. His failure had brought Jerusalem to the brink of disaster. And so, with a broken heart, he asked Isaiah to pray. Not even for his own sake, but for God’s sake—for the sake of His own name. The Rabshakeh had mocked God, not just Jerusalem.

Could Isaiah, who had rebuked him for trusting in human alliances, now plead for mercy on their behalf? Could God deliver them from this terrifying situation?

Isaiah’s response came swiftly, and it was a beacon of light in the darkness. “Thus says the Lord: Do not be afraid of the words that you have heard, with which the servants of the king of Assyria have blasphemed Me. Behold, I will send a spirit upon him, and he shall hear a rumor and return to his own land. And he will be assassinated in his own land.”

These words sparked a flicker of hope in Hezekiah’s heart. The king of Assyria—so powerful, so seemingly invincible—would fall. The God of Israel had not abandoned them. Sennacherib would not have the final say.

Sennacherib’s Letter and Hezekiah’s Prayer

It was then that Sennacherib’s letter arrived, carried by trembling hands into Hezekiah’s presence. The letter mocked the very God of Israel, boasting of Assyria’s victories over countless other nations and their gods. “Do not let your God in whom you trust deceive you by promising that Jerusalem will not be given into the hand of the king of Assyria. Have the gods of the nations delivered them? Where are the gods of Hamath and Arpad? Where are the gods of Sepharvaim? Have they delivered Samaria out of my hand? Who among all the gods of these lands has delivered their lands out of my hand, that the Lord should deliver Jerusalem?”

The letter was a direct assault on Hezekiah’s newfound hope. Mocking the very idea that God could save Jerusalem, and proving his claim with a list of all other gods who had failed against Assyrian might.

But Hezekiah did something remarkable. Instead of giving in to a tangible fear, he took the letter, went up to the temple of the Lord, and spread it out before God. It was a simple, humble act—laying the enemy’s threats before the only One who could answer them.

In the silence of the temple, with the weight of his nation’s survival on his shoulders, Hezekiah prayed. “O Lord of hosts, God of Israel, the One who dwells between the cherubim, You are God, You alone, of all the kingdoms of the earth. You have made heaven and earth. Incline Your ear, O Lord, and hear; open Your eyes, O Lord, and see; all the words of Sennacherib, sent to reproach the living God. Now therefore, O Lord our God, save us from his hand, that all the kingdoms of the earth may know that You are the Lord, You alone.”

The Siege Tightens—Faith vs. Fear

Outside the walls, the Assyrian army continued its preparations for the siege. Soldiers sharpened their weapons, and the people of Jerusalem watched with growing dread. The city of Samaria was fresh in their minds— utterly destroyed by these same Assyrians. Would the same fate befall them? Would their children be taken away, their homes burned to the ground?

Yet inside the city, something was changing. Hezekiah, once a king crippled by the guilt of past mistakes, was now standing firm in the promise of the Lord. He had turned away from his political missteps, from his reliance on foreign powers, and now he placed his trust fully in the God of Israel.

As the people watched the Assyrian army gather like a storm cloud on the horizon, Hezekiah’s resolve began to spread. He shared Isaiah’s prophecy with his soldiers and his people: “Not one arrow will fly from the enemy’s camp. God Himself will deliver us.”

But the question lingered in every heart— The enemy was at the gates, the siege was imminent, and everything seemed stacked against them. Would God truly save them, or would they be crushed like the 46 cities of Judah that paved the way to Jerusalem?

Can you imagine being a soldier on those walls? With the Assyrian army poised to strike, the entire city holds its breath. Will faith in God’s promise stand against the might of the world’s greatest empire? Will Isaiah’s words come to pass, or will the walls of Jerusalem fall, just as Samaria crumbled 20 years ago?

Stay tuned as we uncover the fate of Jerusalem, and the fate of a world dictator: King Sennacherib himself. Will God deliver His people, or will the Assyrian continue to dominate the world scene? Join us next time to find out!

If you’re inspired by the raw & real truth of this story. The palpable weakness & fear mixed with faith & hope to stand firm in an impossible situation. Make sure to share this episode with your friends and family. And don’t forget to subscribe so you never miss an episode of our HnH series!

Other Historical sources of the Assyrian conquest and siege of Jerusalem: |Herodotus Book 2, 141 5th Century BC | |Josephus 1st Century AD, Antiquities of the Jews Book 10, Ch 1 | The Sennacherib Prism in the British Museum |

Links to some of the Bible Texts that inspired this story are found at the top of this letter.