Eight Woes, Eight Warnings (1 of 4)

A Verse-by-Verse Diagnostic of Matthew 23 — Ancient Failures with Contemporary Faces

“Woe to you, experts in the law and you Pharisees, hypocrites! You give a tenth of mint, dill, and cumin, yet you neglect what is more important in the law – justice, mercy, and faithfulness! You should have done these things without neglecting the others.”

— Matthew 23:23 (NET)

Matthew 23 contains either seven or eight Woes, depending on the manuscript tradition. Some manuscripts include a Woe in verse 14 about devouring widows’ houses. This treatment works from the seven Woes present in the earliest manuscripts, though the verse 14 material will be noted where relevant. Each Woe is presented first as Jesus gave it, then as its contemporary equivalent, then as the diagnostic question it produces for the disciple reading it as a mirror.

Read each Woe slowly. Resist the reflex to move quickly to the next one. The specific failure each Woe names has a specific contemporary expression. Find yours before you continue.

WOE ONE Matthew 23:13

“Woe to you, teachers of the law and Pharisees, you hypocrites! You shut the door of the kingdom of heaven in people’s faces. You yourselves do not enter, nor will you let those enter who are trying to.”

The Ancient Failure

The Pharisees blocked the Kingdom in two ways simultaneously. They refused to receive the Kingdom themselves — Jesus, who was the Kingdom arriving in person, stood in front of them and they rejected Him. And their influence on the people prevented those who might have received Him from doing so. The religious authority that was supposed to open the door to God had become the primary obstacle to God. The guides had become the barriers.

The Contemporary Failure

The contemporary version of this Woe is the church or the disciple whose version of Christianity functions as a barrier to the Kingdom rather than a door into it. This takes several specific forms:

• The church that has made denominational affiliation or doctrinal precision the primary test of salvation, producing people who know they are not Catholic or not charismatic or not Reformed but who have no vital relationship with the living God.
• The disciple whose personality, reputation, or public behavior makes the gospel less credible to the people watching him. Who has told people about Jesus in word while showing them something different in life.
• The church culture that is so unwelcoming to the broken, the questioning, and the imperfect that people who were drawing near to God find the community of His people an obstacle to the encounter they were seeking.
• The teaching that substitutes membership, ritual, or morality for the new birth — that leads people to a religion without regeneration and calls it salvation.

The Diagnostic Question

Is there anyone in your life who has moved further from God because of your influence? Not despite your best efforts — because of your actual behavior, your actual words, the actual gap between your profession and your practice? That is the Woe One question. Answer it before moving to Woe Two.

WOE TWO Matthew 23:15

“Woe to you, teachers of the law and Pharisees, you hypocrites! You travel over land and sea to win a single convert, and when you have succeeded, you make them twice as much a child of hell as you are.”

The Ancient Failure

The Pharisees were not passive about their faith. They were zealous missionaries. They worked hard to bring people into the fold. The failure was not in the evangelistic effort. It was in what the convert was being evangelized into. The person who received the Pharisaic gospel received a religion that made them more judgmental, more burdened, more distant from the God of grace and mercy, and more thoroughly convinced of their own righteousness than before. The mission was real. The destination was wrong.

The Contemporary Failure

The contemporary version of this Woe is discipleship that produces Pharisees. That forms people who are more religious but not more like Jesus. More doctrinally precise but less gracious. More culturally separated but less genuinely holy. More certain of their own correctness but less capable of love.

This is the diagnostic test for any discipleship effort: What kind of people does it produce? Not what does it teach, but what does it form? A discipleship method that produces knowledgeable, culturally orthodox, behaviorally compliant, relationally cold, grace-withholding people has produced Pharisees regardless of how sound its curriculum is.

Jesus said the convert becomes twice as much a child of hell as the Pharisee. This is because the convert has now added certainty to the system. The Pharisee at least had the dissonance of knowing he was not fully living the standard. The new convert has been formed by the standard from the beginning and has been given the tools to feel good about his performance. The Pharisaic religion is most dangerous in its second generation.

The Diagnostic Question

Are the people you have discipled more like Jesus than they were before you discipled them? Not more like you — more like Jesus? More generous, more humble, more capable of loving difficult people, more genuinely honest about their own sin? Or more confident in their own religious position and more impatient with those who do not share it?

WOE THREE Matthew 23:16–22

“Woe to you, blind guides! You say, ‘If anyone swears by the temple, it means nothing; but anyone who swears by the gold of the temple is bound by that oath.’ You blind fools! Which is greater: the gold, or the temple that makes the gold sacred?”

The Ancient Failure

The Pharisees had developed an elaborate system of oath-making that distinguished between binding and non-binding oaths — an architecture of evasion designed to allow technical compliance while functionally breaking commitments. If you swore by the temple, the oath was not binding. If you swore by the gold of the temple, it was. By manipulating the categories, a person could make a commitment that sounded solemn and meant nothing.

Jesus had already addressed this in the Sermon on the Mount: “Let your Yes be Yes.” The need for elaborate oath systems is itself the evidence of a culture in which plain speech can no longer be trusted — and the Pharisees had built a religion that institutionalized the untrustworthiness.