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.

3. This would increase Paul’s joy.

“Yes, I want some benefit from you,” Paul says. “I want my heart refreshed in Christ. And the way to do that is for my two sons in the faith to live together as brothers in the Lord.”

The apostle adds one more incentive when he says, in effect, “I’ll probably be passing through your neck of the woods soon, so please set up your guest room for me.” (“No pressure, Philemon, regarding how you’ll respond to my appeal!”)

Though we don’t have a record of Philemon’s response, we know Paul had confidence Philemon would welcome Onesimus home as a brother in the Lord.

Two Trajectories, Two Reminders

Most of us stop reading the letter here, but there are two encouraging and sobering reminders buried at the end.

1. The Case of Mark

In the sign-off, Paul mentions “Mark.” That’s not just some guy named Mark, but Mark, who wrote one of the four Gospels.

Years earlier Mark had assisted Paul and Barnabas (Mark’s cousin) on their first missionary journey. But for some undisclosed reason, he deserted Paul during their trip (Acts 13:13).

Later, when Barnabas wanted to bring Mark along on another journey, Paul and Barnabas had a “sharp disagreement” (Acts 15:39). Paul didn’t want Mark to come along. The relational damage was apparently that deep.

We’re never told how it was resolved. But thanks to this shortest of Paul’s letters, we know that it was resolved. Paul lists Mark as one of his friends and gospel partners. They’ve done what Paul desires Philemon and Onesimus to do.

The little encouragement tucked away in this letter is that Christians of goodwill can have painful separation and unresolved conflict. And yet the end of the story hasn’t yet been written. Perhaps there are former friends who have deeply hurt you, and you don’t yet have the sort of reconciliation that would make things right and rebuild trust. The example of Paul and Mark suggests that though it may take years, God plays the long game. No relationship is irrevocably beyond his repair.

2. The Case of Demas

There’s one more name that stands out in this closing: Demas. Paul’s fellow worker Demas, like Mark, passes along greetings to Philemon.

Does the name Demas sound familiar? It reappears in 2 Timothy—written after the letter to Philemon. In one of the saddest verses Paul ever wrote, he reports that “Demas, in love with this present world, has deserted me” (2 Tim. 4:10).

Demas, who looked and sounded like a gospel partner, was actually an apostate in disguise. He was with them, but never truly one of them (cf. 1 John 2:19). He was a wolf masquerading as a sheep (cf. Matt. 7:15). He chose the broad path of the world rather than the narrow path of the cross.

And even this, it seems to me, strangely encourages in its own way.

Some of us have had those close to us walk away from the Lord and make shipwreck of their faith. It may be a friend or a colleague, a mom or a dad, a brother or a sister, a son or a daughter. It may even be a pastor. After they fall, we often soul-search. Is there something I could have done differently? Something I should have seen? Something I should have said?

I’m thankful Paul doesn’t tell us merely that we are required to “live peaceably with all” (Rom. 12:18). He adds two qualifiers: “If possible, so far as it depends on you, live peaceably with all.”

Though we must make every effort, sometimes—no matter what we do—people we love and trust will ultimately choose to walk away to avoid walking in the light.

At the End of the Day

At the end of the day (quite literally), we must all stand before the Lord. There are some who have abandoned us in this world with whom we will someday reconcile. And there may be some standing with us now who will abandon both us and God.

In the meantime, our calling is to let Christ’s grace reign in our lives (Philemon 1:25). We should fix our eyes on him, the author and finisher of our faith (Heb. 12:2). To whom else can we go?