Expositor's Bible Commentary Commentary Matthew 21:29

"And he answered and said, I will not: but afterward he repented himself, and went." — Matthew 21:29 (ASV)

In this parable, the older son says no, but repents and goes; the second son says yes, but does nothing. Who performs the Father’s will? The first. The story is fairly straightforward. For the first time Jesus openly makes a solemn personal application of one of his parables to the Jewish leaders (v.31).

The shock value of Jesus’ statement can only be appreciated when the low esteem in which tax collectors (see comment on Mk 2:14) were held, not to mention prostitutes, is taken into account. Jesus is saying that the scum of society, though they have said no to God, are repenting, performing the Father’s will, and entering the kingdom; whereas the religious authorities have loudly said yes to God but never do what he says, and therefore they fail to enter. Their righteousness is not enough (cf. 5:20).