What stone would not these words have softened? What wild beast would not these requests have rendered mild and prepared to receive him heartily?… What he had said at the beginning, “having confidence,” that he also says here in the sealing up of his letter.… This also was the part of one who was exceedingly confident. It may also be the case that this statement too was in behalf of Onesimus. For he, not being a neutral personage but rather being intimately knowledgeable about Paul’s situation and special to the apostle, they might lay aside all remembrance of the wrong and might the rather grant the favor.
In order to make Philemon more concerned and more willing to obey, Paul indicates that he will be coming to visit him, for those who are absent are usually ignored. Why should the apostle have refused to go there, when he was always suffering trials and afflictions, beatings, persecutions and imprisonment, and who had no rest other than in Christ? But Paul offered his flesh to suffering for the benefit of believers, in order to obtain immortal crowns for his soul and body. That way the enemies of Christ would be confounded and God's glory would be increased.
Ver. 22. "But withal prepare me also a lodging: for I trust that through your prayers I shall be given unto you."
This also was the part of one who was exceedingly confident — or rather this too was in behalf of Onesimus, that not being indifferent, but knowing that he upon his return would know the things relating to him, they might lay aside all remembrance of the wrong, and might the rather grant the favor. For great was the influence and the honor of Paul residing among them, of Paul in his age, of Paul after imprisonment. Again, it is a proof of their love that he says that they pray; and to attribute to them so much as that they pray for "him." For although I be now in danger, yet nevertheless you will see me if you pray for it.
"But at the same time prepare a lodging for me." I do not think that the Apostle was so rich, and occupied with such great burdens, that he needed a prepared lodging, and that he would not be content with a single cell, a house of small size for his body's limited capacity, but rather to do what he was asked while he was being waited for by Philemon. However, if someone thinks that he was given a command to prepare a lodging for himself, not in a discretionary manner, but truly, the Apostle had to prepare a lodging more than Paul. He was about to go to a new city, to preach the Crucifix, and to impart unheard-of dogmas, knowing that many would come to him; and it was necessary first, that the house be in a celebrated place of the city, to which he could easily be convened. Then, that it be empty of all importunity: that it be spacious, so that it could hold many listeners: not near places of spectacle, not in an unseemly and detestable neighborhood; finally, that it be located on a level site rather than in a cenacle. For which reason, I believe he even stayed in Rome for two years (( "Al." biennio)). And the dwelling place, as I think, was not small, to which the crowds of Jews flowed every day.
For I hope that I will be given to you through your prayers. The Son pleads to the Father, and God grants indulgence, and a brother is often saved by the prayer of his brother. But the Apostle is granted by the prayers of the whole Church, for the benefit of those who are going to hear him. And this gift is said not so much to be on him to whom it is given who is prepared from martyrdom to martyrdom, as on those to whom the Apostle is sent. But that Paul was frequently in prison and was freed from chains, he himself says in another place: "In prisons frequently" (2 Cor. 11), from which sometimes, with the help of the Lord, and frequently even his persecutors finding nothing worthy of death in him, he was let go. For there had not yet been decrees of the Senate against the name of Christian; nor had Nero's sword as yet grown red with Christian blood. But, for the novelty of the new name, either through the envy of wicked men, or the zeal of people eager to destroy their ancient customs, they were sent to prison and again released in a frenzy of popular excitement, which soon subsided. And this is how we say it to be, Acts of the Apostles testify, in which Felix also speaks to Agrippa: that Paul could have been released, if he had not appealed to Caesar (Acts 25). And because he found no reason except for some questions about his own religion, and a certain Jesus, whom Paul preached as alive. From this we observe that, and similarly from other judges, they could have been released, the Lord causing a new preaching to be spread throughout the whole world.
At the same time make ready a lodging for me too. For it was his custom when he was in Colossae to stay in his home. Chrysostom asks what we are to make of this remark in which a poor man commands a rich man by letter from across the expanse of the earth to prepare a lodging for him. What would have to be prepared for one content with bread and cheap victuals? It should be said that it was not for the sake of the preparation of lodging that he says this, but to insinuate familiarity and love; in this way he will be prompt to obey. The Apostle therefore does not say this on account of external trappings but out of his devotion. For I hope that through your prayers I shall be restored to you.
Against this is the fact that he never returned to them but died in Rome, therefore his hope was dashed. I reply that the hope of the just is of two kinds, the chief of which is for his own good, and this is never dashed; another secondary hope is the proof of others, and this is sometimes dashed, because their merits are contrary, as the just man is sometimes not heeded by others. But was he deceived in his trust? It should be said that God alone knows the future; that is not for human knowledge, except the prophetic. And no prophet knows all the future events that concern himself. Only Christ did, because he did not have the Holy Spirit in a limited way. Thus Isaac the great prophet was deceived in Jacob. So it is not to be wondered at in an apostle if he does not know.
Then he ends his letter with a greeting, and first on the part of others, second on his own. He says, they send you greetings, and we read of them at the end of Colossians. But this can be doubted since he mentions Demas. How can this be, since he said in 2. Timothy 3:8, ‘For Demas has deserted me, loving this world’? How, then, can he use his name?
It might be said that he returned to him, but this does not seem to be the case, because this letter was written after that to Timothy and here he says, I hope that through your prayers, and there he foretells his death, saying, ‘The time of my deliverance is at hand.’ Therefore it should be said that Paul was in Rome for nearly nine years, and this letter was written at the beginning, whereas the second letter to Timothy was written at the end of his life and then Demas weary of imprisonment deserted him. The letters of Paul are not arranged chronologically, because the letters to the Corinthians were written before the letter to the Romans, and this before the last letter to Timothy. That is placed first because of its matter, which is worthier. His own greeting here is the same one that ends the second letter to Timothy. Thanks be to God, amen.
[AD 407] John Chrysostom on Philemon 1:21-22