“This is Paul’s only letter that doesn’t mention his apostleship in the greeting. He wants to emphasize to Philemon that he is writing first as a friend, not as a superior. Rather than giving his spiritual son a direct command, he prefers to make his appeal on the basis of love.”

I have a confession to make, one that may sound a little strange: Of all the apostle Paul’s epistles, I think his shortest—the letter to Philemon—may be my favorite.

I’m glad it’s not the only Pauline letter that we have. But it would be a great loss to the church if this little book were not preserved in the canon.

Over the past couple of years, I’ve read through the letter countless times, and I can attest from experience that there are many treasures—unique pieces of insight and wisdom—just waiting to be uncovered.

The Background

The apostle Paul—under house arrest in Rome—dictated a letter to his friend Philemon.

Philemon, a wealthy Christian who hosted a house church in Colossae, had likely converted to Christ years earlier through Paul’s ministry in Ephesus.

After telling Philemon how grateful he is for him and what he prays for him, Paul brings up a name from Philemon’s past: Onesimus.

Onesimus was an unbelieving bondservant or slave who had left Philemon’s household. Reading between the lines, he may have run away—and may have stolen from Philemon in the process.

In the strange providence of God, Onesimus crossed paths with the imprisoned apostle 1,000 miles away in Rome. Through their conversations Onesimus came to trust Christ as Lord and Savior, becoming a spiritual son of Paul—just as Philemon had years earlier.

Now an old man, and dependent on others’ help due to his imprisonment, Paul longed for Onesimus to stay with him.

But convenience and comfort were not the ultimate drivers for Paul. The gospel was. Even though sending Onesimus away would be like sending his very heart, Paul saw the reunion of Philemon and Onesimus as an opportunity for both men to provide the church—and the world—with a living parable of gospel reconciliation and partnership.

The Messenger

This wasn’t the only letter Paul wrote during this imprisonment. He likely wrote to the Ephesians and Colossians at the same time.

And in Colossians (remember Philemon also lived in Colossae), we get a fascinating little nugget. Paul says that the courier Tychicus will “tell you all about my activities.” And he’ll have a traveling companion: “Onesimus, our faithful and beloved brother, who is one of you” (Col. 4:7, 9).

So how did the letter to Philemon—along with the letters to the Ephesians and Colossians—travel a thousand miles from Rome to Asia Minor? Through the messengers Tychicus and Onesimus.

So we can picture Onesimus, with rolled up parchment in his sweaty hand, knocking on the front door of his estranged master. He then hands him this letter from Paul which explains how Onesimus has become a Christian and pleads for the two of them to reconcile.

Note, too, that there was no “silent reading” in the ancient world. And Paul addressed the letter not only to Philemon, but also to Apphia (probably Philemon’s wife), Archippus (probably Philemon’s son), and the entire house church.

It’s a powerful scene to picture: Philemon reading the letter aloud in Onesimus’s presence.

The Ask

This is Paul’s only letter that doesn’t mention his apostleship in the greeting. He wants to emphasize to Philemon that he is writing first as a friend, not as a superior. Rather than giving his spiritual son a direct command, he prefers to make his appeal on the basis of love. Building a love-based rhetorical masterpiece, Paul writes in such a way that Philemon will not be forced to grudgingly concede but will gladly comply of his own accord. Paul frames his appeal so that it’s an offer that Philemon will want to accept.

Paul gives several enticements along the way. Here are three.

1. This would be gain.

Philemon wouldn’t just be getting his bondservant back—he’d be also gaining a beloved brother in the Lord. You want to see people in your church come to faith and expand your spiritual family, Philemon? Well, consider this a gift.

2. There is nothing to lose.

If Onesimus stole anything from him when he ran away or is in debt in any way, Paul effectively says, “Put it on my tab. You happen to owe your very life to me, Philemon, but I promise to repay you anything Onesimus owes.” Paul wants Philemon to receive Onesimus as he would receive Paul himself.

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