Part Five · Chapter Twenty
Who Were the Pharisees, and Who Are We? (2 of 2)
Failure Three: They Did Everything for an Audience
“Everything they do is done for people to see.” (23:5)
This is the failure that Matthew 6 addressed in the Sermon on the Mount: the displacement of the Father as the primary audience by the crowd as the primary audience. The Pharisees made their phylacteries wide and their tassels long. They sought the places of honor at banquets and the most important seats in the synagogues. They loved to be greeted with respect in the marketplaces and to be called ‘Rabbi.’
Every one of these behaviors is the same behavior. It is the use of religious activity as social currency — the performance of piety in exchange for status, respect, and approval. The Father has been removed from the audience. The crowd has replaced Him. And the result, as Part Four established, is the displacement of the knowing by the performance.
The Contemporary Pharisee
Before the Woes themselves are examined in Chapter Twenty-One, the disciple needs to locate the contemporary equivalents of the Pharisaic failures. The specific expressions change between generations. The root failures do not.
The contemporary Pharisee is not primarily the legalist who refuses to drink. That stereotype is too easy and too dismissible. The contemporary Pharisee is the person who has mastered the performance of Christianity — who knows the vocabulary, maintains the practices, holds the correct opinions, attends the right conferences, reads the right authors, and has produced a religious life that is impressive by every visible metric while the interior life remains largely unexamined.
He is the pastor who preaches sacrifice and lives in luxury. He is the elder who enforces church discipline on others while his own marriage is quietly dying. He is the theological blogger who demolishes heresy online and treats his children with contempt at home. He is the worship leader whose heart is far from the God his voice is celebrating. He is the missionary who has given everything to the field and nothing to the people at his own table.
And he is, potentially, any of us. That is the point of Part Five. Not to identify the Pharisees in your church. To find the Pharisee in yourself.
Jesus’ sharpest warnings in the Gospels were not directed at the irreligious, the pagan, or the openly sinful. They were directed at the most religious people of His generation. That fact should produce not smugness but trembling in every person who takes their faith seriously enough to be reading this handbook.
How to Read the Woes
Chapter Twenty-One will work through all seven Woes verse by verse. Before that chapter begins, three principles for reading them correctly.
Principle One: Read Them as Mercy, Not Condemnation
Jesus wept over Jerusalem immediately after the Woes (Luke 19:41). He did not pronounce the Woes with relish. He pronounced them with grief — the grief of the Shepherd who sees the wolves in sheep’s clothing and knows what they are doing to the flock. The Woes are not the language of contempt. They are the language of a doctor who has been asked to examine a patient and will not soften the diagnosis to spare the patient’s feelings.
When you read the Woes as a mirror, read them with the same spirit. Not with self-condemnation — the Spirit convicts and restores; He does not destroy. With the honest grief of a disciple who wants to see clearly so that what is broken can be healed.
Principle Two: The Woes Address the Interior, Not Primarily the Exterior
The specific behaviors Jesus condemns — widened phylacteries, lengthy tassels, cleaned cups, whitewashed tombs — are exterior symptoms of interior conditions. Jesus is not primarily concerned with the width of the phylactery. He is concerned with the heart that makes a man widen it.
When you use the Woes as a diagnostic, resist the temptation to examine your exterior behaviors in isolation. The question is never “Do I do this specific thing?” The question is always “Is the interior condition that produces this specific thing present in me?” The Pharisee who switched from wide phylacteries to narrow ones would not have been less of a Pharisee. He would just have been a Pharisee with a different external marker.
Principle Three: The Woes Are Not About Them
This is the principle that the entire structure of Part Five rests on. The Woes are not about the Pharisees of the first century. They are about the religious person of every century, including this one, including you.
Read Matthew 23 with your name in the margin. Not their name. Yours. Not “Woe to you, teachers of the law and Pharisees, you hypocrites” as a description of someone you know at church. “Woe to me” — when I close the Kingdom to others by my failures. “Woe to me” — when I tithe precisely and neglect justice. “Woe to me” — when I clean the outside and leave the inside filthy. Read it that way. It is significantly more useful.

