Beginning in Matthew 23:1, Jesus delivers a prophetic woe-speech in the tradition of the Old Testament prophets. Although the details of the speech focuses on the Pharisees and their traditions, these seven woes can be applied to any religious hypocrisy.
Before looking at the seven woes, where is Matthew 23:14? In the KJV, Matthew 23:14 reads “Woe unto you, scribes and Pharisees, hypocrites! for ye devour widows’ houses, and for a pretence make long prayer: therefore ye shall receive the greater damnation.” All modern translations omit the entire verse, it was probably added to Matthew 23 based on Mark 12:40 and Luke 11:47. In some manuscripts the line appears before verse 13, in others it appears after.
Shutting the Kingdom in People’s Faces (23:13). The first woe imagines the kingdom of heaven as a walled city that can be locked to prevent unauthorized entry. In Matthew 16:19 Jesus gives the “keys to the kingdom” to Peter, for example.
The Pharisees have shut the door to the kingdom for some people in two ways. First, they consider some people unworthy of the kingdom, the “the tax collectors and other sinners.” Second, they may be preventing people from hearing Jesus’s teaching, effectively “shutting the door” on people who want to enter the kingdom. Previously Jesus has described the outsiders entering the kingdom, or the Pharisees not entering or entering last. Matthew 8:10-12, many will come from the east and west to enter the kingdom before the Pharisees.
Corrupting Converts (23:15). There is very little evidence Jews did anything like evangelism in the first century. However, proselytes did exist. Nicolas of Antioch (Acts 6:5), there were “devout converts in Antioch (Acts 13:43), and Izates (in Josephus) are examples. It is possible this refers to God-fearing Gentiles, people like Cornelius who were attracted to the ethics and practices of Judaism but did not fully convert by submitting to circumcision.
If they do make a convert, the new convert is “twice the son of hell” that the Pharisee is. If the Pharisee is a hypocrite, the new convert is even more severe and strict than even the Pharisees. Often new converts are zealous
Swearing Oaths (23:16-22). Jesus calls the Pharisees blind guides and will be called blind three more times in the chapter. In Matthew 15:14 he called them blind guides in a discussion of hand washing. Romans 2:19 says some Jews considered themselves “guides for the blind,” although Paul also says they are hypocritical. Jesus taught on swearing oaths in the Sermon on the Mount (Matt 5:33-37). Although the Law permitted oaths, Jesus tells his disciples to not to swear oaths at all, but to “let your yes be yes.” For Jesus and his disciples, all oaths are binding: if you promise something, you must fulfill that promise.
As in the Sermon on the Mount, the problem was not swearing an oath, but finding ways to set the oath aside. Jesus gives two sets of conditions as examples. If one swears by the temple, the oath can be set aside, but swearing by the gold of the temple the oath is binding. It is not clear what “gold of the temple” refers to, possibly the “wealth of the temple.” If someone swears by the altar, the oath can be set aside, but if one swears by the gift on the altar, it is binding.
m.Nedarim 1:3 He who says, “Not— unconsecrated produce shall I not eat with you,” “Not-valid [food],” and, “Not pure,” “[Not] clean [for the altar],” or “Unclean,” or “Remnant,” or “Refuse”—is bound. [If he said, “May it be to me] like the lamb [of the daily whole offering],” “Like the [temple] sheds,” “Like the wood,” “Like the fire,” “Like the altar,” “Like the sanctuary,” “Like Jerusalem”— [if] he vowed by the name of one of any of the utensils used for the altar, even though he has not used the word qorban—lo, this one has vowed [in as binding a way as if he had vowed] by qorban. R. Judah says, “He who says, ‘Jerusalem,’ has said nothing.”
The Pharisees may have regarded an oath made in anything other than the name of the Lord or his attributes as not binding. If you swear a binding oath, it must be in the name of the Lord. If this is the case, then verse 20-21 points out the hypocrisy, if one swears by the temple, then are in fact swearing by God because God dwells in it; if one swears by heaven or the throne of God, one swears by God since he dwells there.
The first three of the seven woes may have shocked and offended the original audience. Modern readers are often surprised that Jesus harshly condemned hypocrites, usually because they tend to think of Jesus as teaching pure love as a non-confrontational preacher of kindness. But Jesus is not saying it is wrong to make converts or swear oaths. The problem is the hypocrite focuses so much on traditional practices they miss the grace God is extended to sinners, inviting them to wedding banquet as well.