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Woe

When we see the word WOE in the scripture, particularly when Jesus uses it, we know we better pay attention. Jesus has lots to say, all prefaced with WOE! Jesus is speaking to the leaders of the day. Jesus is speaking to the elites. Is Jesus speaking to me?

I am going to pay attention. Jesus is talking to me. I must learn.

This is critical in my life. I don’t want to be a hypocrite.

Whenever we see the word “woe” in the New Testament, then it is always a translation of the Greek word “ouai”. This Greek word “ouai” is used 47 times in the New Testament: 41 times in 33 verses it is translated as “woe”, and six times in three verses it is translated as “alas”.

It’s Greek to me!

Those are the only times “woe” and “alas” appear in the New Testament. So, let’s look at the meaning of this Greek word, and then see why the translators translated it as “alas” in six places.

The Greek word “ouai” is used in the following three ways:

  • It is used to express a denunciation, i.e. it is used to pronounce someone or something as blameworthy and evil.
  • It is used to express a severe calamity, a severe distress or affliction.
  • It is used to express great grief.

While these meanings overlap, each one has a different focus. And in each case, it is always the context in which “ouai” is used that shows which specific focus is intended. Most of the time it is used to express a denunciation, i.e. it is used to pronounce someone or something as blameworthy and evil.


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Seven times in Matthew 23, Jesus the Messiah, says these words to the religious leaders and elites of that time, the scribes, and the Pharisees. And in all seven cases Jesus identified these religious leaders as hypocrites. In one additional “woe unto you” statement Jesus Christ called those people blind leaders (i.e., “blind guides”).

What was Jesus the Messiah telling these religious elites (scribes and Pharisees) with these “woe unto you” statements? Did Jesus mean the same thing He meant when He made this statement to Judas? Or are these statements to the Pharisees only a softened version of the Messiah’s statement to Judas?

Can we call a spade a spade, and can we face up to the facts? Let’s look at the first WOE from Jesus.

But woe unto you, scribes and Pharisees, hypocrites! For you shut up the kingdom of heaven against men: for you neither go in yourselves, neither suffer you them that are entering to go in.

~Jesus  | Matthew 23:13

Let’s dig deeper …

  • The most outstanding characteristic of these religious leaders was hypocrisy. Hypocrisy refers to acting and pretending. Hypocrisy means teaching things that they knew were not true. It means not putting into practice in their own lives the things they authoritatively told others to do.
  • Their heretical teachings were shutting off access to God’s Kingdom for people who potentially had access to God’s truth. This point is also applicable in our world today. If people today are drawn into a church group that teaches heresies, then the ministers in that group are effectively shutting off access to God’s Kingdom for their followers.
  • The religious elites (Pharisees) were not going to be in God’s Kingdom (i.e., “you neither go in yourselves”). That means that the Pharisees were heading for the lake of fire. Yes, at that stage those Pharisees still had the possibility of repenting and changing course. And a small number of them did (e.g., Paul). But as a group they were certainly heading towards the second death.
  • The expression “neither suffer you them that are entering to go in” means that the Pharisees did their hardest to persecute those who were trying to live by God’s laws in sincerity and truth. False teachers never like it when someone practices the truth; they are incensed when people believe the truth. That type of response was also true for the Pharisees, where the Apostle Paul before his conversion was the most outstanding example of this trait.

One lesson here is …

If you knowingly teach things that are false to God’s people, then you will be in the lake of fire, and then it will be “woe unto you”. Hypocrites always know better, but they teach falsehoods anyway.