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