The six woes in Isaiah 5 are roughly parallel to the eight woes that Jesus proclaimed in Matthew 23. Jesus’ second woe in Matt. 23:14 was added later by an unknown scribe and should not be part of Scripture. The Wycliffe Bible Commentary says, “Verse 14 is an interpolation from Mark 12:40 and Luke 20:47” but does not comment on the validity of the verse itself.

The NASB puts it in brackets, implying that it was added later. Panin’s Numeric New Testament omits it, because, if it were to be included, the verse would destroy the numeric patterns that are evident in all inspired Scripture.

I personally defer to Ivan Panin, who judged all such additions and discrepancies by the mathematics within the text itself. In fact, it was because of his discovery of these numeric patterns in 1890 that he was converted from agnosticism to a strong belief in Christ, testifying that no man could have written a book like this.

Karl Sabiers, who wrote Russian Scientist Proves Divine Inspiration of Bible during the last year of Panin's life, wrote:

“After his college days he became an outstanding lecturer on the subject of literary criticism... His lectures were delivered in colleges and before exclusive literary clubs in many cities of the United States and Canada. During this time Mr. Panin became well known as a firm agnostic— so well known that when he discarded his agnosticism and accepted the Christian faith the newspapers carried headlines telling of his conversion.”

This conversion occurred in 1890 when his attention was caught by the first chapter of John, in which the article (“the”) is used before “God” in one instance, and left out in the next: “and the Word was with the God, and the Word was God.” He began to examine the text to see if there was an underlying pattern contributing to this peculiarity. Making parallel lists of verses with and without the article, he discovered that there was an entire system of mathematical relationships underlying the text. This led to his conversion to Christianity, as attested to by his publication in 1891 of The Structure of the Bible: A Proof of the Verbal Inspiration of Scripture.

Until his death in 1942, Ivan Panin labored continuously on the discovery of numerical patterns throughout the Hebrew language of the Old Testament and the Greek language of the New Testament, often to the detriment of his health. His conclusion was that if these patterns were implemented intentionally by man, the collaboration of all writers of the Bible—stretched over many disparate years—would be required, in addition to the condition that each of them be a mathematician of the highest order.

In 1899 Panin sent a letter to the New York Sun challenging his audience to disprove his thesis that the numerical structure of scripture showed its divine origin.

https://en.wikipedia.org/wiki/Ivan_Panin

It appears that some later scribe decided to embellish Jesus’ first woe, but this is only a fleshly commentary on it, not Scripture itself. So by omitting Matt. 23:14, we are left with just seven woes to link to Isaiah’s six. Also, Jesus’ woes are all directed against the “hypocrites” except for the fourth in Matt. 23:16. It appears, then, that Jesus’ fourth woe was simply an extension of the third and not to be considered a separate woe against the hypocrites.

So if we consider the third and fourth to be one, then we are down to just six woes, and these relate directly to Isaiah’s six. Further, Jesus’ woes did not follow the same order as Isaiah’s woes. In studying them, I perceive that the two sets should be linked as follows:

1. Isaiah 5:8 and Matthew 23:13

2. Isaiah 5:11 and Matthew 23:25

3. Isaiah 5:18 and Matthew 23:15, 16

4. Isaiah 5:20 and Matthew 23:27

5. Isaiah 5:21 and Matthew 23:29

6. Isaiah 5:22 and Matthew 23:23

We will study each of these in turn.

Link #1: Isaiah 5:8 and Matthew 23:13

Isaiah’s first woe is directed against the rich creditors who foreclose on the houses of the poor and refuse to keep the Jubilee. In Matthew 23:13 we read,

¹³ But woe to you, scribes and Pharisees, hypocrites, because you shut off the kingdom of heaven from people; for you do not enter in yourselves, nor do you allow those who are entering to go in.

The scribal commentary in Matthew 23:14 is this:

[¹⁴ Woe to you, scribes and Pharisees, hypocrites, because you devour widows’ houses, and for a pretense you make long prayers; therefore you will receive greater condemnation.]

Because this commentary was interpolated from other passages of Scripture, it was actually a very good explanation of the previous verse. The hypocrisy of the religious leaders in shutting off the kingdom of heaven in verse 13 is explained in verse 14 as keeping widows from entering their houses. In other words, the rich and powerful were foreclosing on widows’ houses, and the spiritual counterpart was to keep people from entering the kingdom of heaven (their real “house”).

This obviously corresponds directly to Isaiah 5:8, “Woe to those who add house to house.” Jesus’ woe adds a spiritual meaning to Isaiah’s woe and interprets it in New Covenant terms.

Link #2: Isaiah 5:11 and Matthew 23:25

These woes condemn men for their misguided priorities. Isaiah 5:11, 12 condemn the people for preferring entertainment, self-indulgence, and drinking parties rather than studying the word of God. The people try to find satisfaction in fleshly desires, while their lack of godly knowledge destroys them.

Jesus said in Matthew 23:25, 26,

²⁵ Woe to you, scribes and Pharisees, hypocrites! For you clean the outside of the cup and of the dish, but inside they are full of robbery and self-indulgence. ²⁶ You blind Pharisees, first clean the inside of the cup and of the dish, so that the outside of it may become clean also.

The Pharisees were not known for having fun per se, but their priorities were wrong. Most of their rules focused upon laws of cleansing, but they were based on the Old Covenant idea that one’s actions could cleanse the heart. Jesus turned this around, telling them that it was their evil hearts that defiled their bodies. New Covenant believers are cleansed by the water of the word (John 15:3) and by the Holy Spirit’s “fire” working within (Matt. 3:12, 13).

While Isaiah condemns the people for their “self-indulgence,” Jesus interprets this as focusing upon the flesh—outward religion. The flesh has its place, but one’s priorities must be right.

Link #3: Isaiah 5:18 and Matthew 23:15, 16

Isaiah 5:18 was a condemnation of cynical idolatry, where men paraded their false gods on a cart drawn by their “cords of falsehood.” If anyone dared to turn them toward the true God of Israel, they replied cynically that the promises of God had failed to come to pass.

Matthew 23:15, 16 interprets this and enlarges upon it, saying,

¹⁵ Woe to you, scribes and Pharisees, hypocrites, because you travel around on sea and land to make one proselyte; and when he becomes one, you make him twice as much a son of hell [gehenna] as yourselves. ¹⁶ Woe to you, blind guides, who say, “Whoever swears by the temple, that is nothing; but whoever swears by the gold of the temple is obligated.”

The subtle comparison between the idolaters in Isaiah’s day and the religious leaders in Jesus’ day can be seen here. An idolatrous parade in Isaiah’s day was an advertisement honoring false gods and, by implication, a call to worship them. In other words, they were seeking proselytes to false religion.

Jesus treats the religion of His day as a call to false worship, not based upon outward idols, which the Jews banned, but heart idolatry as seen in Ezekiel 14:3, 4. Idolatry was occurring in Ezekiel’s day, though the priests and elders probably would have denied this. Jesus said it was occurring in His own time as well, although that too was disputed by the religious leaders.

First century Judaism, then, had produced many sons of “hell” (gehenna), and the proselytes had been recruited to the same form of religion. There is a difference between hades and gehenna, although many translate both Greek words as “hell,” as if they were the same thing. Hades is the state of the dead, which corresponds to the Hebrew word Sheol, “the grave.” Gehenna corresponds to the Hebrew ben-hinnom, the name of the valley outside of Jerusalem, where, in earlier times, men had offered up their children to Baal, burning them in the fire.

Jer. 19:4, 5, 6 condemns the religious activities in the valley of Ben-hinnom, saying,

⁴ “Because they have forsaken Me and have made this an alien place and have burned sacrifices in it to other gods… and because they have filled this place with the blood of the innocent ⁵ and have built the high places of Baal to burn their sons in the fire as burnt offerings to Baal, a thing which I never commanded or spoke of, nor did it ever enter My mind; ⁶ therefore, behold, the days are coming,” declares the Lord, “when this place will no longer be called Topheth [“burning”] or the valley of Ben-hinnom, but rather the valley of Slaughter.

Jeremiah’s prophecy turns this geographical location into a prophetic place of “slaughter” for Jerusalem and its inhabitants. He illustrated it by taking an earthen jar and smashing it in this valley, prophesying in Jer. 19:11, “Just so will I break this people and this city, even as one breaks a potter’s vessel, which cannot again be repaired.”

The valley of Ben-hinnom, or Gehenna, then, became a prophetic place representing the final destruction of the earthly Jerusalem. To be a “son of Gehenna” was to be included in the great slaughter that is yet to come when the city is destroyed. Becoming a proselyte to Judaism does not bring anyone closer to God but puts them in danger of slaughter—particularly if they move to Jerusalem.

This ought to be a warning to anyone living in Jerusalem today. Sooner or later, the city will be destroyed so completely that it “cannot again be repaired.” It was destroyed often in the past, but it was always repaired and rebuilt. So Jeremiah’s prophecy has to be completed. When it is fulfilled, “Hagar” (Jerusalem) and her fleshly children (children of the Old Covenant) will be “cast out” (Gal. 4:30).

The prophetic significance of Gehenna was explained in greater detail, along with Hades and Tartarus, in my book, The Judgments of the Divine Law. Each is a different type of judgment.

Jews, then, should not be cynical about the coming of Christ, for although it has been nearly 2,000 years since He promised to return, He will indeed return. They should stop dragging around their false god (heart idolatry), and certainly no one should follow the “blind guides” who induce others to become proselytes to Judaism—which only makes them “sons of gehenna.”

Jesus described this false religion in Matt. 23:17-22, showing essentially that it worships gold and values it more than the temple and its altar. Children of the flesh, or spiritual Ishmaelites, are concerned with material things. Jesus thus links Judaism to the worship of the golden calf that Aaron built in the time of Moses (Exodus 32:19, 20).

Link #4: Isaiah 5:20 and Matthew 23:27

In Matthew 23:27, 28 Jesus says,

²⁷ Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed sepulchers which on the outside appear beautiful but inside they are full of dead men’s bones and all uncleanness. ²⁸ So you, too, outwardly appear righteous to men, but inwardly you are full of hypocrisy and lawlessness [anomia].

Their outward show of righteousness was designed to hide their inward “uncleanness,” so that they could call evil good and good evil. Elsewhere the scribes and Pharisees were called wolves in sheep’s clothing (Matt. 7:15). Dressed in wool, the wolves were calling themselves good when in fact they were evil.

So Isaiah condemns Jerusalem, saying, “Woe to those who call evil good and good evil, who substitute darkness for light and light for darkness” (Isaiah 5:20). Likewise, the leaders had either changed the law, reinterpreted it to allow the desires of the flesh to have their way, or simply ignored it altogether.

Link #5: Isaiah 5:21 and Matthew 23:29

Isaiah 5:21 is short and includes no explanation:

²¹ Woe to those who are wise in their own eyes and clever in their own sight.

I explained this earlier by connecting it with Matt. 23:29, 30,

²⁹ Woe to you, scribes and Pharisees, hypocrites! For you build the tombs of the prophets and adorn the monuments of the righteous, ³⁰ and say, “If we had been living in the days of our fathers, we would not have been partners with them in shedding the blood of the prophets.”

Their wisdom and cleverness were earthly and soulish, not heavenly and spiritual. Scripture does not doubt their mental intelligence but their ability to hear the word and to interpret it according to the mind and intent of the Lawgiver.

The chief evidence is the fact that many generations of people in Jerusalem had killed the prophets. Their hearts did not change over time. It was only after the prophets were safely dead and buried that they were honored, for then they were able to interpret their writings according to the darkness of their own hearts. The prophets were no longer in the position to correct their misinterpretations.

Hence, when the Messiah came on the scene, most of the scribes and Pharisees were unable to hear His words. The main difference was that after killing Him, they failed to honor Him as they did the earlier prophets.

Perhaps this is because they knew that He had been raised from the dead and was an ongoing threat to their belief system. They were unable to adopt Him as one of their own, as they tried to do with the other prophets.

This woe comes with more explanation in Matt. 23:31-33,

³¹ So you testify against yourselves that you are the sons of those who murdered the prophets. ³² Fill up, then, the measure of the guilt of your fathers. ³³ You serpents, you brood of vipers, how will you escape the sentence of hell [gehenna]?

They were about to fill up the measure of their fathers by killing the Messiah. This was a Hebrew idiom picturing sin as a slow drip into a measuring cup. Divine judgment would come only after the cup was full and overflowing, as with the “Amorites” in Gen. 15:16 (KJV).

The destruction of Jerusalem was thus imminent, brought about by their final rejection of the Messiah. Jesus had much to say about the city’s coming destruction, but after being destroyed in 70 A.D., it was later “repaired” and rebuilt. Hence there is yet a greater fulfillment coming, one which will figuratively cast the city into gehenna, where, according to Jer. 19:10, 11, it will never again be rebuilt.

Link #6: Isaiah 5:22 and Matthew 23:23

Isaiah 5:22, 23 condemns the people of Jerusalem for perverting justice by taking bribes, drinking on the job, and denying the people their God-given rights. Jesus’ woe in Matt. 23:23, 24 condemned Jerusalem for the same thing, saying,

²³ Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cumin and have neglected the weightier provisions of the law: justice and mercy and faithfulness; but these are the things you should have done without neglecting the others. ²⁴ You blind guides, who strain out a gnat and swallow a camel.

Those who had planted a few spices around the house were supposed to tithe even that, said the Pharisees. Jesus did not condemn such tithes, but He clearly showed that the religious leaders were nitpicking while abandoning the things that God thought were truly important. Gnats were unclean creatures, and the people were not supposed to eat them, but gnats can be quite persistent, and it can be difficult to keep them out of one’s mouth. To be “righteous,” the people often took pains to cover their mouths to “strain out a gnat,” but they readily swallowed “camels” (also unclean).

Such was their hypocritical subversion of “justice and mercy and faithfulness.” It is important to know what the law says about both justice and mercy, for there are laws regulating both. The law is not only about justice. The sacrificial laws, for example, were laws of mercy, for they provided a way of absolving sin by transferring the penalty to an innocent animal.

Another example of mercy is seen in the law of restitution. Normal restitution was to pay double that which had been stolen (Exodus 22:4). However, if a person repented and confessed his sin on his own, without first being caught and tried, he only had to return the stolen item and pay one-fifth of its value in restitution (Num. 5:6, 7). The law is thus merciful to the repentant.

Jesus’ emphasis on faithfulness is not well understood by most people, because they do not know the connection between faith and truth. But the Hebrew word for faith (aman) means “to believe, to have faith, truth.” One’s faith is only an illusion apart from truth, for if a man believes a lie, it is not biblical faith. Hence, when Jesus spoke of faithfulness in connection with justice and mercy, He was referring primarily to believing truth.

In a court of law, all three are necessary to judge matters. There must be justice, but the judge must also know how mercy can be applied lawfully. And none of these are possible without knowing the truth through the testimony of witnesses. Faith comes by hearing the word of Christ, Paul says in Rom. 10:17, because the word of Christ testified of the truth. So it is with all judgment. Testimony under oath is spoken, and when we hear truth, we believe (have faith in) what has been spoken.

Jerusalem had subverted justice, mercy, and faithfulness to the truth, and for this reason, they would soon crucify the Messiah, even as the city had killed the prophets. The fleshly nature of the city, its leaders, and its people, had not changed significantly since the days of Isaiah. For this reason, Paul identified the earthly city as being “Hagar” and its citizens “children of the flesh” (Rom. 9:8; Gal. 4:29).

Instead of trying to make Jerusalem’s Ishmaelites into the heirs of the Kingdom through the Old Covenant, we ought to show them how to become children of Sarah, who represents the New Covenant. This involves a renunciation of Hagar. One must “cast out the bondwoman and her son” (Gal. 4:30). This is done by being begotten by the Spirit, so that we may become true sons of God.