The word for “woe” in Greek is to express grief and the way it is used in verse 27, the grief is what the scribes and Pharisees will feel after their death in hell because of their hypocrisy. The reason the religious leaders were condemned by the Lord is because they were sending people to hell even though they knew the Scriptures.
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 as yourselves. -Matthew 23:15
The scribes and Pharisees deceived people with intent for gain. They loved money and fame more than God.
And they love the place of honor at banquets, and the seats of honor in the synagogues, 7 and personal greetings in the marketplaces, and being called Rabbi by the people. -Matthew 23:6
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. -Matthew 23:25
The scribes and Pharisees are what you would call today false Christian leaders. Jesus described them as a whitewashed which one plasters the tomb with to make it white and clean. A false Christian comes the same way. They will look like a genuine believer in the outside, talking like a Christian, but inside the person is spiritually dead. Jesus being the Son of God, saw through their facade and knew that they were as false as one can get. They were living double lives.
Another way that a false teacher can be exposed is to examine their lifestyle. A false believer will be filled with greed and pride, putting himself above others. In verse 28, it describes them as lawless. The word “lawlessness” means one who lives without God’s law in their heart. They will give you the impression that they live according to God’s Word but privately, when no other Christian is watching, they live for the world and its pleasures.
A false prophet or teacher can only hide for so long. It will be a matter of time before God exposes them by taking off their Christian mask for the benefit and safety of the saints. God can use anything to uncover what is hidden and in our time, the Lord used politics. With politics, you will see if a professing Christian will walk the talk by aligning himself or herself with those who are pro-life and are against the homosexual agenda. Folks, a Christian has to be one 24-7 in all area of life not just in the church. A false one will oppose you when you stand up for good and righteousness. I’m telling you, there are so many wolves hiding in Christian garments.
Friend, we are living in a time where it will be very difficult to know who really is from the Lord. Many look so much like a Christian that it is almost impossible to tell the difference. Be very careful who you let into your life for spiritual growth. You might be letting in a wolf that will destroy your faith. Jesus warned us that before the rapture of the church, there will be many false prophets to deceive as many people as possible. Your only safety net is the Scriptures and prayer. Stick close to Jesus and you won’t be fooled.