Condensed from my Mission Course (2008).
What, you’d cast expensive pearls before swine? No one would think of doing that then or today. So it was a good basis on which Jesus could build a case for discernment. Swine don’t eat pearls. They don’t know the value of pearls so can’t appreciate them for their true value. If you feed swine pearls, they may be looking for something to eat and, determining pearls not to be food, turn against you and attack you in angry response.
In the process of doing all that, they may also be trampling those same pearls underfoot. What a pity. So if swine don’t value pearls, there is no sense in giving them pearls. That is precisely the point that Jesus wanted to make. A little discernment and a dose of good judgment are necessary when communicating the gospel. Not only is it counterproductive to insist on giving the good news to those who resist it but it can boomerang against you.
The context was the query by John the Baptist’s disciples about the lack of fasting from Jesus’ disciples. Jesus showed his authority over religious rituals the people had developed into traditions.
Then he explained that new spiritual insights could not be expected to fit into the old traditional mold. Even when given light, the overwhelming response would be that “the old is better.”
The difficulty is that new wine teaching would so challenge the wineskin of established understanding that it would crack. This is not to suggest that new wine is superior to old wineskins. They just need to be kept separate – new wine in new wineskins and old wine in old wineskins. But Jesus cautioned against new wine in old wineskins.