Introduction: There are eight blessings pronounced in Matthew 5:3-12. By contrast, there are eight woes pronounced in Matthew 23:13-36. Part One focused on the first twenty verses of what is commonly called "The Sermon on the Mount" (Matthew, chapters 5 - 7). Part Two is a discussion from our Lord's lament of the scribes and Pharisees for their insincere hypocritical ways. The Greek word for "woe" is an interjection of grief or denunciation. Though Jesus denounces them, it would be good to consider that Jesus was in a state of sadness concerning them and the effect they were having on others. See this spirit in Matthew 23:37-39; Luke 19:41-44 cp. I Samuel 15:10-11; Psalm 126:5-6; Jeremiah 9:1-3; Lamentations 3:48-51; Romans 9:1-8; 10:1-4; Galatians 4:8-11,19-20; Philippians 3:17-19. Our fellowship with the Lord means that "mad" must be combined with "sad." See Philippians 3:10. Suffering affects heart and mind - not just the body.

The eight blessings promoted qualities that were not natural pleasures, but joys that were of a divine nature. However, these eight woes are very natural for many zealous religious people. The consequences are disastrous. They can only be avoided by having a sincere relationship with the Son of God. See Matthew 7:21-27; John 3:14-21; 4:10,14; 5:21-24,39; 6:27-29,35-45.63; 7:16-18,37-39; 8:30-36; 10:9-11,14-18,27-30; 11:25-26; 14:1-6; 15:1-8; 16:33; 17:1-26.

Jesus' ministry tended to encourage those who were lowly and needy. His ministry also tended to confront and humble those who were proud. In either case Jesus warned everyone about ignorance, pride, selfishness, hypocrisy and insincerity - whether it be their own or that of others. Matthew 23:1-12 sets the stage for Jesus to pronounce eight woes. The problem with receiving such messages is that we do not know where we fit in. Some are in a miserable condition and don't know it. Others know they are miserable and they don't understand why, but they think they do. They often blame others. With the help of God's Spirit we can be humble and hungry for God's counsel and help. Consider Luke 6:20-26. Here, Jesus presents blessings and woes together. "He who has ears to hear, let him hear!"

The twenty-third chapter of Matthew specifically teaches us the failure of Israel, as they denied and rejected their Messiah (Matthew 21:33-46 cp. Psalm 118:22-23; Isaiah 53:1-12). This chapter also teaches us the sad and woeful situation of all who are self-righteous, falsely religious, of a critical spirit, or simply proud and highly opinionated and assertive about a lot of things in life. Discernment is needed to know when not to judge others on a personal level (Matthew 7:1-5) - avoiding hypocrisy, and to know when we need to examine the fruit of teachers and leaders (Matthew 7:15-20) - avoiding the deception of them who are false.

Below are the eight woes of Matthew 23:13-36 that we will consider. On what kind of people does the Lord pronounce woe?

• Matthew 23:13 - They Are Roadblocks to the Lord's Ways


• Matthew 23:14 - They Are Pious Predators


• Matthew 23:15 - They Are Zealous and Contagious


• Matthew 23:16-22 - They Are Blind and Authoritarian


• Matthew 23:23-24 - They Are Occupied with Lesser Things


• Matthew 23:25-26 - They Are Occupied with Superficial Things


• Matthew 23:27-28 - They Are Spiritually Dead and Hypocritical


• Matthew 23:29-36 - They Are Deadly Impostors of Religious Tradition

Below are the blessings of being a true member of Christ's Kingdom in this world.

• Matthew 5:3 - "Blessed are the poor in spirit…"


• Matthew 5:4 - "Blessed are they that mourn…"


• Matthew 5:5 - "Blessed are the meek…"


• Matthew 5:6 - "Blessed are they which do hunger and thirst for righteousness…"


• Matthew 5:7 - "Blessed are the merciful…"


• Matthew 5:8 - "Blessed are the pure in heart…"


• Matthew 5:9 - "Blessed are the peacemakers…"


• Matthew 5:10-12 - "Blessed are they which are persecuted for righteousness' sake…for My sake"

As you compare the woes with the blessings, you will not discover a simple matchup of eight things with eight other things. The eight woes create a picture. The eight blessings create another picture. It is these two pictures that you must compare. So, this series will only benefit you as you analyze, meditate, and make application. This is not an academic pursuit. It is a spiritual exercise that will test your soul and hopefully cause you to gain discernment.

• Romans 12:1-3; 16:17-19


• Ephesians 4:11-16


• Colossians 1:3-13; 2:1-10


• Philippians 1:8-11


• II Timothy 3:13-17; 4:1-5


• James 3:8 - 4:10 cp. I Peter 5:1-11


• I John 2:18-27; 4:1-16


• Jude 1:3-4,8,10-13,16-25

Second Scripture Reading: Matthew 23:13-39

More detail on Matthew 23:13-36
Below are the eight woes of Matthew 23:13-36 that we will consider. On what kind of people does the Lord pronounce woe?

Matthew 23:13 - They Are Roadblocks to the Lord's Ways.
As if locking a door, they have taken away the key of knowledge (Pure Scripture) and contaminated the truth with man-made doctrines (Luke 11:52). They stole God's words and established their own system of righteousness. See Proverbs 30:5-6; Jeremiah 23:21-22,30-32; Romans 10:1-4; Matthew 7:13-20.

Matthew 23:14 - They Are Pious Predators.
The Pharisees would do estate planning for widows, convincing them to make large donations to the temple or to them personally. Part of their "charm" was to make long prayers, creating the impression that they were close to God, therefore trustworthy, and should be supported. See II Timothy 3:1-7; Matthew 6:5-6; James 1:27; Acts 20:25-35; I Thessalonians 2:1-10.

Matthew 23:15 - They Are Zealous and Contagious.
Zealous efforts to make converts are too often met by those who want to zealously fling themselves into some great cause to promote and defend. The Pharisees would reproduce their own kind, making them even worse than themselves. See I Corinthians 15:33-34; Galatians 5:7-9 cp. Matthew 16:5-12.

Matthew 23:16-22 - They Are Blind and Authoritarian.
The Pharisees made complicated rules about oaths that were made. They put binding obligations on others if they swore by gold or gifts that were offered. They put significance on wealth and religious form, but they did not focus on God's name and authority. They lacked true reverence. See Matthew 6:9-10; II Corinthians 7:1; II Timothy 3:5; Hebrews 12:28.

Matthew 23:23-24 - They Are Occupied with Lesser Things.
The Pharisees would emphasize details, overlooking larger issues. Jesus did not condemn them for tithing garden herbs, but the larger matter was tithing on major harvests of crops (Leviticus 27:30). Pharisees would strain their drinks through a fine cloth to avoid swallowing a gnat. This was the least of the prohibited animals (Leviticus 11:23). Metaphorically, Jesus said their careless handling of the law was like swallowing a camel - the greatest of prohibited animals (Leviticus 11:4). See God's appeal for us to have godly priorities and to give attention to the best things (Psalm 51:6,16-19; Jeremiah 9:24; Hosea 6:6; Micah 6:6-8; Luke 10:38-42).

Matthew 23:25-26 - They Are Occupied with Superficial Things.
Outward appearance meant everything to the Pharisees. They carefully sought the respect and approval of men, but they made no real effort to have their hearts and minds right with God. This is compared to washing the outside of the cup and dish, but not cleaning the insides which determine the real quality of drinking and eating. See Matthew 5:20; Deuteronomy 6:4-6; Titus 1:15-16; I Samuel 15:30; 16:7; Romans 2:28-29; John 12:42-43 (Condemning Christ, they hypocritically kept their religious rules - John 18:28).

Matthew 23:27-28 - They Are Spiritually Dead and Hypocritical.
A second illustration of false appearances is that of tombs that are painted with whitewash on the outside, but inside of them are the rotting remains of dead bodies. It is distasteful to drink and eat from filthy cups and dishes, but now we consider that the Pharisees are loathsome and lifeless before God. See Isaiah 64:6; James 2:20; Hebrews 9:14; II Corinthians 5:17.

Matthew 23:29-36 - They Are Deadly Impostors of Religious Tradition.
Beware of those who emphasize a great religious heritage, who at the same time lack Scriptural integrity. While the Pharisees were trying to identify with God's prophets by building monuments to them, they could not see that they were just like the people of Israel who had killed those prophets. Their Messiah was about to be killed by them. The Lord's apostles and other preachers would follow the same destiny. Jesus' lament, in Mattthew 23:33-39. seems to indicate the terrible destruction of Jerusalem in A.D. 70. See John 16:1-3,33; Matthew 10:16-17; 27:22-25 (cp. Acts 5:26-28); Acts 2:22-24; I John 3:1; II Timothy 2:8-10; Romans 8:31-39.

Closing Thoughts - Other Scriptures to Ponder
Jesus had very serious discussions with Jewish leaders. He confronted unfaithful, shallow, and proud religion. Do Jesus' words confront us personally?

• Matthew 7:15-29; 15:1-14; 16:1-12; 23:1-39


• Luke 5:17-32; 16:13-15; 18:9-14


• John 3:1-21; 5:8-47; 6:26-66; 7:14-44; 8:1-59; 10:1-42


• Consider the challenge Moses gave to Israel, "Behold, I set before you this day a blessing and a curse…" - Deuteronomy 11:26-28 cp. Deuteronomy 11:29-32; 27:1 - 28:68; Hebrews 3:1-6.

If we are to think with the mind of Christ, we must also confront the issues that exist with those who "… profess to know God, but in works they deny Him…" (Titus 1:16). Also consider:

• I Corinthians 2:12-16


• II Corinthians 2:14-17


• I Thessalonians 5:21-22


• I Timothy 2:14-16; 4:12-16


• II Timothy 3:13 - 4:5.