Ambrosiaster : Although he asked three times, his request was not granted. It is not that he was disregarded but that he was making a plea which was against his own best interests. — COMMENTARY ON PAUL'S EPISTLES Gregory the Dialogist : If the Father gives us everything we ask in the name of the Son, what then does it mean that Paul asked the Lord three times and did not deserve to be heard, but it was said to him: "My grace is sufficient for you, for power is made perfect in weakness"? Did not that most excellent preacher ask in the name of the Son? Why then did he not receive what he asked? How then is it true that whatever we ask the Father in the name of the Son, the Father gives us, if the Apostle asked in the name of the Son that the angel of Satan be removed from him, and yet did not receive what he asked? But since the name of the Son is Jesus, and Jesus means savior, or is also called salvation, therefore he asks in the name of the Savior who asks for that which pertains to true salvation. For if something that is not expedient is asked for, the Father is not being asked in the name of Jesus. Hence it is that Paul also is not heard, because if he were freed from the temptation, it would not profit him unto salvation. — Forty Gospel Homilies, Homily 27 John Chrysostom : Accordingly, whether we have our requests granted or not, let us persist in asking and render thanks not only when we gain what we ask but also when we fail to. Failure to gain, you see, when that is what God wants, is not worse than succeeding; we do not know what is to our advantage in this regard in the way he does understand. The result is, then, that succeeding or failing we ought to give thanks. Why are you surprised that we don't know what is to our advantage? Paul, a man of such quality and stature, judged worthy of ineffable blessings, did not know what was advantageous in his requests: when he saw himself beset with trouble and diverse tribulations, he prayed to be rid of them, not once or twice but many times. "Three times I asked the Lord," he says.… "Three" means he asked frequently without success. So let us see how he was affected by it: surely he didn't take it badly? He didn't turn fainthearted, did he? He didn't become dispirited, did he? Not at all. On the contrary, what? God said, "My grace is sufficient for you; my power has its full effect in weakness." Not only did he not free him of the troubles afflicting him, but he even allowed him to persevere in them. True enough; but how does it emerge that he did not take it badly? Listen to Paul's own words when he learned what the Lord had decided: "I will gladly boast of my weaknesses." Not only, he says, do I no longer seek to be rid of them, but I even boast of them with greater satisfaction. Do you see his grateful spirit? Do you see his love for God?… So we ought to yield to the Creator of our nature, and with joy and great relish accept those things that he has decided on and have an eye not to the appearance of events but to the decisions of the Lord. After all, he who knows better than we what is for our benefit also knows what steps must be taken for our salvation. — HOMILIES ON Genesis 30.16 John Chrysostom : "Concerning this thing I besought the Lord thrice." That is, oftentimes. This also is a mark of great lowliness of mind, his not concealing that he could not bear those insidious plottings, that he fainted under them and was reduced to pray for deliverance. — Homily 26 on 2 Corinthians