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What the Fathers say
Eastern Fathers
John Chrysostom
See how great is his prudence, how he confesses the man's faults, and thereby extinguishes his anger. I know, he says, that he was unprofitable. "But now" he will be "profitable to thee and to me." He has not said he will be useful to thee, lest he should contradict it, but he has introduced his own person, that his hopes may seem worthy of credit, "But now," he says, "profitable to thee and to me." For if he was profitable to Paul, who required so great strictness, much more would he be so to his master.
Theophylact of Ohrid
"He was once useless to you." He knows that confession of sin extinguishes wrath; therefore he speaks thus. "But now is useful both to you and to me; I am sending him back." Since he became pious and holy, and therefore, he says, he is useful to both of us. If he is useful to Paul, who requires such great zeal, then certainly to Philemon as well. At the same time, he also implies that if he is useful to me, then he ought to be sent back to me. That is, I hand him over to you; use him as you wish. …
Oecumenius
"formerly useless to you". For he knows that the acknowledged sin is to extinguish the master's anger. "but now indeed useful both to you and to me". If such faithfulness is useful to Paul, who demands so much, it is clearly also useful to Philemon.
Western Saints
Jerome
Who, although he was once useless to his master (for a slave who steals and runs away harms no one but his own master), now on the contrary, by way of compensation for his usefulness to both his master and Paul, and to others through Paul, he deserves more love than he had previously deserved hatred. …
Thomas Aquinas
Second, there is the change in status. For if he had persevered in sin, he would not be worthy of leniency. Note that Paul says little and means much. For as Cicero taught, one ought to make little of one's own deed as much as possible. Thus the Apostle speaks lightly of his offence, saying, He once was useless to you, that is, harmful in taking away your possession, but now, converted from evil to the state of virtue, he is useful for the service of God and man. …
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