In Matthew 19:17–21, Jesus had not spoken harshly to the rich man, and in Mark 10:21, we read that he loved him. Jesus thus showed the importance of not judging him too harshly, but in Matthew 19:23, he now warned the disciples about how difficult it is for the rich to enter the kingdom.
Jesus’ made this statement in the context of him instructing his apostles about how matters should be in the church, so after the discussion with the man, he now, in Matthew 19:23, as in Matthew 19:14, speaks to the apostles personally. He does so with the strong emphasis of the phrase Truly, I say to you.
He shows that his command to the man in Matthew 19:21 was a special case, for he does not say that a rich man cannot enter the kingdom unless he gives everything away, but rather that a rich man only enters it with difficulty, since he faces more obstacles along the path than the poor would (Luke 6:20). Possessions can draw one away from Christ, as the more you have, the more you worry. The man could not fulfill Jesus’ command in Matthew 19:21 because of his wealth.
In the preceding verses (Matthew 19:17–21), Jesus had not spoken in a harsh or condemning manner concerning the rich man. On the contrary, in Mark 10:21 we read that he loved him. Jesus therefore conveyed the importance of not judging him too harshly. At the same time, in Matthew 19:23, he now warned the disciples, reminding them of how difficult it is for the rich such as this young man to enter the kingdom of heaven.1
This statement by Jesus needs to be understood within the context of him instructing his apostles concerning how matters ought to be later in the church, and so following the discussion with the rich young man he now in Matthew 19:23 also turns—like in Matthew 19:14—to the apostles, addressing them personally. He does so with a strong word introduced by the phrase Truly, I say to you.
Jesus here affirms that his command to the rich young man in Matthew 19:21 constituted a special prescription, for he does not say that a rich man cannot enter the kingdom of heaven unless he first gives everything away, but rather that a rich man only enters it with difficulty. This means that he faces more obstacles along the path than the poor would (Luke 6:20). Possessions can draw one away from Christ, as the more you have, the more you worry. The young man was specifically unable to fulfill Jesus’ command in Matthew 19:21 because of the fact that he was so rich.2
23 And Jesus said to his disciples, “Truly, I say to you, only with difficulty will a rich person enter the kingdom of heaven.