“I say to you that likewise there will be more...

There is joy in heaven, joy in the presence of the angels of God, over one sinner that repenteth, as those publicans and sinners did, some of them at least (and, if but one of them did repent, Christ would reckon it worth his while), more than over a great number of just persons, who need no repentance. Observe,

The repentance and conversion of sinners on earth are matter of joy and rejoicing in heaven. It is possible that the greatest sinners may be brought to repentance. While there is life there is hope, and the worst are not to be despaired of and the worst of sinners, if they repent and turn, shall find mercy. Yet this is not all, God will delight to show them mercy, will reckon their conversion a return for all the expense he has been at upon them. There is always joy in heaven. God rejoiceth in all his works, but particularly in the works of his grace. He rejoiceth to do good to penitent sinners, with his whole heart and his whole soul. He rejoiceth not only in the conversion of churches and nations, but even over one sinner that repenteth, though but one. The good angels will be glad that mercy is shown them, so far are they from repining at it, though those of their nature that sinned be left to perish, and no mercy shown to them though those sinners that repent, that are so mean, and have been so vile, are, upon their repentance, to be taken into communion with them, and shortly to be made like them, and equal to them. The conversion of sinners is the joy of angels, and they gladly become ministering spirits to them for their good, upon their conversion. The redemption of mankind was matter of joy in the presence of the angels for they sung, Glory to God in the highest, Luke 2:14.

There is more joy over one sinner that repenteth, and turneth to be religious from a course of life that had been notoriously vile and vicious, than there is over ninety-nine just persons, who need no repentance.

More joy for the redemption and salvation of fallen man than for the preservation and confirmation of the angels that stand, and did indeed need no repentance.

More joy for the conversion of the sinners of the Gentiles, and of those publicans that now heard Christ preach, than for all the praises and devotions, and all the God I thank thee, of the Pharisees, and the other self-justifying Jews, who though that they needed no repentance, and that therefore God should abundantly rejoice in them, and make his boast of them, as those that were most his honour but Christ tells them that it was quite otherwise, that God was more praised in, and pleased with, the penitent broken heart of one of those despised, envied sinners, than all the long prayers which the scribes and Pharisees made, who could not see any thing amiss in themselves.

Nay, More joy for the conversion of one such great sinner, such a Pharisee as Paul had been in his time, than for the regular conversion of one that had always conducted himself decently and well, and comparatively needs no repentance, needs not such a universal change of the life as those great sinners need. Not but that it is best not to go astray but the grace of God, both in the power and the pity of that grace, is more manifested in the reducing of great sinners than in the conducting of those that never went astray. And many times those that have been great sinners before their conversion prove more eminently and zealously good after, of which Paul is an instance, and therefore in him God was greatly glorified, Galatians 1:24. They to whom much is forgiven will love much. It is spoken after the manner of men. We are moved with a more sensible joy for the recovery of what we had lost than for the continuance of what we had always enjoyed, for health out of sickness than for health without sickness. It is as life from the dead. A constant course of religion may in itself be more valuable, and yet a sudden return from an evil course and way of sin may yield a more surprising pleasure. Now if there is such joy in heaven, for the conversion of sinners, then the Pharisees were very much strangers to a heavenly spirit, who did all they could to hinder it and were grieved at it, and who were exasperated at Christ when he was doing a piece of work that was of all others most grateful to Heaven. - Matthew Henry