In the history of the Jewish people there were many times that could be called “lost opportunities.” Such opportunities existed, for example, before the sin of the Golden Calf, before the Jewish people entered the land, as well as during the times of Kings Saul and Solomon. Yet, the opportunity faded or did not turn into what it could have been.
The life of Hezekiah, king of Judea, was also such an opportunity. Indeed, he represented the last great opportunity for Judea. His story is the watershed in the history of the First Temple.
The Talmud (Sanhedrin 94a) tells us that God wanted to make Hezekiah the Messiah. Had he fulfilled his Messianic potential, history as we know it – including the destruction of the Temple – would not have happened.
Ironically, the life of Hezekiah was sandwiched between two wicked people: his father Ahaz and his son Manasseh. In a great effort to counteract the idolatrous ways his father had accustomed the people to, Hezekiah embarked on an ambitious campaign to build one of the greatest school systems in the history of the Jewish people. He succeeded. “From the territory of Dan in the north to Beersheba in the south… there was not a child who did not know the most complex laws of purity and impurity,” the Talmud related (Sanhedrin 94b).
However, Hezekiah also understood that in a minute they could revert back idolatry. He knew the weaknesses of the Jewish people. And he worried about them even as he rebuilt Jewish society like few before him.
The Assyrian Horde
During his reign, Judea was beset by two great powers: first Aram, and then Assyria, who swallowed up Aram and then the Ten Tribes of the Northern Kingdom.
Assyria had built the mightiest army the world had ever seen and was led by the great warrior, Sennacherib. After destroying Samaria and sending the Ten Tribes into exile, he wanted to make a clean sweep into Judea, sack Jerusalem and continue all the way to Egypt.
Indeed, his army swept into Judea and conquered its fortified cities (II Kings 18:13). Out of desperation, Hezekiah tried to buy off Sennacherib and offered him all the treasure in his palace and in the Temple. It did not work. Sennacherib came and laid siege to Jerusalem.
At this frightful moment, the prophet Isaiah stepped forth and assured Hezekiah of salvation (II Kings 19:6-7). People of real faith do not lose heart even in terrible times. Hezekiah strengthened himself and refused to surrender.
It was in the Middle of the Night
On the night of Passover, in the middle of the night, an angel smote the army of Assyria and 185,000 died from a plague (II Kings 19:35).
Imagine — the Jewish people were staring annihilation in the face. An overwhelming implacable foe completely surrounded their last stronghold. There was a constant propaganda barrage against them in their native tongue. They had doubters from within. They went to sleep Passover night with no realistic hope.
However, they woke up the morning of Passover and the threat was suddenly gone. Someone had smitten the outstretched arm of the enemy with the sword it had raised against them.
At that moment, the Talmud remarks, Hezekiah had the chance to become the Messiah. All he had to do was sing the praises of God. Moses and the people had done so after the Egyptians were drowned in the sea. Had Hezekiah done the same he would have been the Messiah and history as we know it would have proceeded differently.
However, he did not sing. That is why he was not worthy to be the Messiah. The opportunity was lost.
Three days later, before the end of Passover, Hezekiah became ill. According to Tradition, it was a terminal illness that no one had ever recovered from. Worse, the prophet Isaiah told him that he was going to die from this illness (Isaiah 38:1).
Hezekiah was not fazed, and gave the prophet an answer for the ages that became one of the more famous lines in the Talmud (Berachos 10a): “Never give up hope even when there is a sword on your neck.” What an incredible lesson! When a prophet like Isaiah tells a person that he is going to die it is as if God Himself signs the death warrant. What could be more certain? However, Hezekiah had something even more certain: a profound belief in the power of prayer, a power emanating from the highest will of God Himself, which had the ability to overturn even a prophecy decreeing death.
And that is what happened. Hezekiah prayed to God with great fervor to heal him and went on to live another 15 years. Tradition teaches that he was the first person to recover from such an illness.
The Mistake after the Victory
After Assyria was defeated, Babylon rose to prominence. They sent emissaries to Hezekiah because they were impressed that he had defeated Assyria. He accepted the emissaries and did something he is severely castigated for: he took them into the Temple and showed them the Holy Ark. He even took off the lid of the Ark and showed them the Tablets of the Ten Commandments inside.
“They are the secret of our success,” he told them.
The Sages said that he had no right to show it to them. Furthermore, the Ark was not the secret of their success. Earlier in history it had been captured by the Philistines. There is no artifact, no matter how holy – even the Tablets of the Ten Commandments – that saves the Jewish people. The only thing on Earth that can save the Jewish people is the Jewish people. It is people that count.
The Sages say that that is why Manasseh became who he became. It was a reaction to his father’s behavior in the episode.
The story of Hezekiah is not possible to tell without telling the story of Isaiah.
Isaiah was the greatest prophet of the Jewish people after Moses. He possessed oratorical and literary gifts greater than of any other. His words today, thousands of years later, are still like lightning bolts. That is why he is the most quoted prophet, who uttered the most famous lines: “The wolf will lie down with the lamb” (Isaiah 11:6; see also 65:25). “They will turn their swords into ploughshares” (Isaiah 2:4). “Holy, holy, holy is the God of Hosts – the entire world is filled with His glory” (Isaiah 6:3). And many other such examples.
Ultimately, his greatness was that he was able to see beyond the gloom and destruction. He saw the lost opportunity of Hezekiah. He saw the rise of his grandson, Manasseh, the incarnation of evil. He saw Babylon rising to become the dominant empire. He himself had been told by God to prophesize the destruction of Jerusalem and the Temple. He was a critic of the social imbalance and failings of the Jewish people.
And yet he is the most glorious prophet of hope, portraying in the grandest terms the eternal vision of the Jewish people and their redemption.
That itself is greatness. We know people who are optimists. We know people who are pessimists. We do not know too many people who are both.
Isaiah was such a person. At one and the same time he was both the prophet of doom and destruction as well as the prophet of redemption and consolation.
The picture of this epoch is not complete without including the story of Manasseh.
He was evil incarnate. Among the many evils he perpetrated was the murder of his grandfather, the prophet Isaiah.
Even more than the murder of his grandfather was the murder of everything his righteous father stood for. Manasseh literally and figuratively tore down everything his father built, defiling the Temple and restoring all the corrupt, idolatrous ways of his worst predecessors.
At the same time, he did wonders for the economy. Bad kings are sometimes like that: bad for the social fabric, good for the stock market. In the final analysis, though, Manasseh was an evil man who brought much evil to the people — so much so that he is explicitly cited in the Talmud as someone who lost his portion in the World to Come.
If he would have been good, following on the heels of his father, then civilization would have been different. Judea’s descent into the abyss of societal idolatry, murder and immorality steepened until eventually there no escape from the destruction.
In truth, it would be another 120 years after Hezekiah that the Temple would be destroyed. At that time, there would be no miraculous event to save the people. In many ways, though, their fate was sealed by the man who would not be Messiah. After Hezekiah’s opportunity lost, doom and destruction quickened their inexorable march toward the doorstep of Judea.
 His name means, “he whom God has strengthened [hizzeko]” (Talmud, Sanhedrin 94a).
 Talmud, Yevamos 49b.
 Sanhedrin 90b. The Talmud says that the only thing that helped Manasseh was suffering, which God afflicted him with in the latter part of his life (Sanhedrin 101b, Ruth Rabbah 5:6). That helped him review his ways and have a change of heart. He tore down the idols and tried to rebuild was he had destroyed. Nevertheless, it was not enough to earn him to regain what he had lost (however, see Sanhedrin 102b).