Philemon: Christian Diplomacy

When we open the book of Philemon, we are immediately struck with its uniqueness.
It is Paul’s shortest yet most intimate letter.
As a masterpiece of diplomacy, the key concepts of this letter center on
    grace and compassion. It may be paraphrased as follows:

“Paul, a prisoner for Jesus’ sake, and our brother Timothy, to our beloved friend and co-worker Philemon. And to our beloved sister Apphia and to Archippus, our fellowsoldier and the church that meets in your home: spiritual blessings and peace be yours from God our Father and the Lord Jesus Christ. (vv. 1-3)

I perpetually thank God for you in my prayers, for I continually hear of the love and faithfulness you demonstrate toward Christ and fellow Believers. I know the generosity that springs from your faith will result in the public recognition of the many blessings Christ bestows. I have derived much joy and comfort from your love, for you have refreshed the hearts of fellow Believers, my dear brother.  (vv. 4-7)

Although I have the liberty to use my authority in Christ to command you concerning your duty, I prefer to appeal to you on the basis of love, for I am growing older and am now in prison for the sake of Jesus Christ. I plead with you for my son Onesimus, for I have become his spiritual father here during my imprisonment. Although formerly he was not beneficial to you, now, true to his name, he has become beneficial to both of us. I am returning him to you, and in so doing am sending back one who is the object of my deepest affection. I would have preferred to retain him here to serve me on your behalf during my imprisonment for the sake of the Gospel. (vv. 8-13)

However, without your approval I would not do this, in order that your response will be voluntary rather than compulsory. Perhaps the reason he was temporarily separated from you was providential, for now you can receive him back eternally. Although he belongs to you as a servant, now he is a beloved brother. Although he is dear to me, how much more so is he now to you, both as a servant and a fellow Believer? (vv. 14-16)

Because you count me as your close friend, welcome him as you would me. If he has cheated you or owes you anything, charge that to me. I, Paul, personally guarantee this in my own handwriting, knowing I need not remind you of your spiritual indebtedness to me. Yes, brother, do me this kindness for the Lord’s sake: your Christ-like spirit will cheer my heart. Convinced of your compliance, I am confident you will do even more than I ask. (vv. 17-21)

Prepare a guest room for me as well, for I trust through your prayers I will be visiting you in the near future. Epaphras, my fellowprisoner for the cause of Christ, sends his regards. My co-workers Mark, Aristarchus, Demas and Luke send their greetings as well. May the spiritual blessings of the Lord Jesus Christ be with your spirit. Amen.”  (vv. 22-25)

Although we may assume many things about this epistle, the internal evidence provides only the following facts:

1. Philemon had a slave or servant named Onesimus.
2. For reasons unknown to us, Onesimus had fled from Colossae to Rome.
3. Some how, Onesimus had sought out Paul.
4. After his conversion, Onesimus wanted to return to Philemon.
5. Paul was apprehensive of some difficulty when Onesimus returned to Philemon.
6. Paul wrote to persuade Philemon to receive Onesimus back as a brother in Christ.

Philemon is a book about opportunities. There was an opportunity for Onesimus to verify his conversion by expressing his sorrow, making restitution and returning to Philemon. There was an opportunity for Philemon to prove his reputation as a Believer by accepting Onesimus back as a brother, rather than a slave. There was an opportunity for Paul to mediate in this situation by sending this letter back with Onesimus and Tychicus.

Philemon is a book about interpersonal relationships. However, it is also about how we handle relationships. In these twenty-five verses, we discover Philemon’s relation to Paul, Paul’s relation to Onesimus, Philemon’s relation to Onesimus and how all are related to Jesus Christ.

Philemon is a book about responsibilities. Duty demanded Paul send Onesimus back. Duty demanded that Onesimus return voluntarily. Duty demanded Philemon accept him back. Paul wrote to eliminate any possibility Onesimus would not be received favorably.

In this letter, there are three major players. First, there is the apostle Paul. Because he wrote so much of the New Testament, we know a great deal about him. Nothing endears us to him more than the great Apostle, writing from a prison cell, pleading for a poor runaway slave. Here we see Paul in a defining moment as he pleads for one in desperate need of an intercessor. 

The second character is Philemon. In a sense, he is a minor character, for he is never mentioned outside of the book. Almost everything that can be known about Philemon can only be discovered within the book itself. Paul appeals to his reputation for kindness and compassion and provides him with a perfect opportunity to live up to his reputation. There are two minor characters briefly mentioned in the letter. Apphia is assumed to be Philemon’s wife. Paul addresses her as one who also has an interest in Onesimus. Archippus was probably the son of Philemon and Apphia.

Finally, we have Onesimus. It cannot be conclusively proven that Onesimus was indeed a slave. The language used within the letter would also allow him to a servant in Philemon’s employ. But his name is a common name of slaves, meaning “valuable or profitable.” Owners often named their slaves, hoping they would live up to their names. If he was a slave, Onesimus was on the bottom rung of the social ladder in the first century. A Roman slave was a nonperson. Roman slaves were bought and sold as the dregs of humanity. They served as proof the Romans were superior over all other races. A slave was a walking household accessory. Such persons were always guilty till proven innocent. A slave had no rights. He could own nothing. He could not get married. He could not produce children, except if his master wanted more slaves. A slave could seek nothing for himself. He could only seek the good of his master. For the slightest offense, a slave could be scourged, mutilated, thrown to wild animals or crucified. Aristotle said there should be no friendship with a slave. Severe incarceration penalties were imposed on anyone in Rome who harbored a runaway slave. There is an irony here. Since Paul was already in jail, what more could they do to him?

If Onesimus was a runaway Phrygian slave, he only did what many would expect a slave would do: attempt to escape, defraud and steal from his master. The moral cesspool called Rome was a natural hiding place for such men. Paul could not have found Onesimus, for Paul was in prison (Acts 28:30). Therefore, Onesimus must have come to Paul. But what drove him to seek out Paul? Was it fear? Was it the memory of Paul in his master Philemon’s home? Was it conviction? Was it hunger pangs or the pangs of his conscience? All such suggestions fall under the realm of conjecture.

Paul wrote to address a specific problem. He seems reluctant to send Onesimus back to Philemon without an “insurance policy.” This letter serves as that policy. Slaves were frequently killed for lesser offences. Although Onesimus had repented, he had not made restitution. By running away, Onesimus deprived Philemon of his services during his absence. Freedom in Christ does not mean freedom from responsibility. Perhaps Philemon’s character was damaged, for Onesimus’ absence could have inferred he had been was a cruel master.

In this letter we see the affection between a convert and the one who has led him to Christ. We find in this epistle how we need to take personal responsibility for those we mentor. In it we see the positive, persuasive spirit of Christianity. The letter to Philemon throws light on the sensitivity, compassion and character of Paul. It reveals to us the power of positive, godly persuasion. While Paul’s other epistles teach compassion for others, here is an example of faith in action. Paul shows how theology is turned into practicality.

Paul writes a letter to Philemon that is courteous, delicate, gentle, warm, kind, affectionate, tender, and loving. It is private, discrete, urgent, dignified, persuasive, tactful, and sincere. Paul uses every possible angle of approach to achieve his objective. In effect, Paul tells Philemon “We have the same goals, the same friends, and the same Jesus.” Appealing to Philemon’s good character, Paul asks him to consider his advanced age and his incarceration. With beautiful strategy, Paul builds a watertight case nearly impossible to ignore or reject. Jesus had promised to give His followers wisdom no one will be able to resist (Lk. 21:15).

Philemon is “The Polite Epistle.” It is a tract that teaches tact. The letter is the sole model for personal diplomacy in the Word of God. As God’s Word, it is more than a window into Paul’s heart: it is a window into God’s heart. It is totally concerned with an incident of Christian domestic life in the first century. It is what Paul does not say, but only suggests, that makes this epistle so powerful.

But Paul’s plea must not be confused with trying to con Philemon. Neither was Paul using reverse psychology or some form of “Christianized coercion.” A manipulator’s tactics presuppose the manipulator has something to gain. In Paul’s situation, it was the exact opposite. He was losing the help Onesimus could have provided. Paul was not doing what was best for himself, but what was best for Onesimus.

His thoughts are refined and he pens his letter using a wonderful blend of compassion and logic. In every verse, Paul employs various thoughts, suggestions and strategies to reach his objective:

I am in jail for Jesus’ sake.  v. 1
Philemon, you’re a beloved brother, a good friend and co-laborer. v. 1
Your home is a church!  v. 2
I am praying for you.  v. 2
I wish you grace and peace from God and His Son.  v. 3
I thank God for you and pray for you constantly.  v. 4
You love God and you love the saints.  v. 5
Your life already demonstrates your love.  v. 5
Christ has wrought a great work in your life. v. 6
Your Christianity touches many lives.  v. 7
I am comforted by thinking about your love.  v. 7
You are my brother.  v. 7
I have the authority to command you: but I will not.  vv. 8-9
I am an old man and a prisoner for Jesus sake.  v. 9
Onesimus is my son in the faith. v. 10
I am pleading on his behalf.  v. 10
He was converted while I am in jail.  v. 10
We are now all brothers in Christ!  v. 10
Onesimus is now profitable to you.  v. 11
I trust Onesimus: I am sure you will too.  v. 12
He is a part of my life.  v. 12
I could keep him here with me: but I will not.  v. 13
I know you would have been here for me, if you could have been.  v. 13
Remember I am in jail for Jesus’ sake.  v. 13
I respect you.  v. 14
God is involved in this situation.  v. 15
Onesimus has changed for the better.  v. 15
He is now God’s eternal possession and yours as well.  v. 15
Onesimus is dear to me, but I know he is now even more dear to you.  v. 16
Receive him as you would me.  v. 17
I will pay his debts: consider this letter my promissory note.  vv. 18-19
You owe me your soul: but I will not mention it.  v. 19
I ask only this one favor.  v. 20
Do this for my sake, for it will bring me joy.  v. 20
Your spirit is like Christ’s.  v. 20
Do this for Jesus’ sake.  v. 20
I am confident of your obedience.  v. 21
I know you’ll be obedient to God as well.  v. 21
I am sure you will go above and beyond the call of duty.  v. 21
I know your prayers will hasten my release from prison.  v. 22
I am coming to visit you after I am released.  v. 22
While you are preparing a room for Onesimus, prepare one for me too.  v. 22
Our mutual brothers in Christ also send you their greetings.  vv. 23-24
I know the grace of God will be with you and direct you.  v. 25
Amen: let this come to pass; let it be so.  v. 25

The letter begins and ends with grace (vv. 3 & 25).
From its introduction to its conclusion, the Gospel of Christ is a gospel of grace.

Onesimus had no defense for his sins, so he had to make a choice. Either keep on running, or surrender his life into the hands of the only one who cared enough to intercede. He chose to trust the only one who reached out to him. The same Holy Spirit that led Onesimus to seek out Paul leads every Believer to seek out Jesus. No one can easily repair their broken relationship with their master. Sinners steal from him, deprive him, cheat him, and run from him. But sooner or later, one gets tired of running. He or she may suspect they will eventually get caught and have to pay for their transgressions. It is at the point of our desperation, we seek someone who will be our mediator. 

Onesimus was a fugitive from justice. Paul does not seek to minimize his sins, but implores Philemon to forgive his sins. The letter is an entreaty by a brother, to another brother, on behalf of another brother. Paul had only one basis on which to plead his case for Onesimus: the grace of Onesimus’ master. Onesimus had nothing to recommend him but his raw need. God’s grace is always extended to the weak, the helpless, those who cannot defend themselves, the widows, the orphans, the children, the babies, the elderly, the sick, the prisoner, and the slave. Ponder the grace of God in God keeping this little memo as part of the canon of Scripture to show us His love for the lost. Picture the mighty Apostle Paul, in a dungeon for Jesus’ sake, pleading for the life of a man most would consider a hopeless case; a lost cause. Consider this helpless nonperson, this man without a country, with no one to plead his case, no one to redeem him, and no one to help him. But he finds one person who saw his true value as a human being. Paul did not say, “I cannot get my hands dirty with his situation.” Paul had both the power and the influence to save him.

Paul laid aside his rights and interceded on behalf of another. If there is pivotal verse in the epistle, it is verse nineteen. Paul offered to pay whatever Onesimus owed and make full restitution for him. In effect, Paul said “Impute his demerits to me.” Whatever sins or wrongs Onesimus may have done do not matter anymore. Paul offered to pay Onesimus’ debts as if he had accrued them himself. In this situation, there was no one but Paul who could have paid his debts. He now has a champion, a Savior that will pay all he owed.

As Paul left no stone unturned to change Onesimus’ relationship to his master, so Christ spared no effort to change our relationship to the Father. Paul’s pleadings on behalf of Onesimus verify God specializes in “lost causes,” deeming them worthy of intercession. “In Christ Jesus there is neither Jew nor Gentile: slave or free; but Christ is all in all” (Col. 3:11). “In Christ Jesus there are neither slaves or free men; neither male nor female, for we are all one in Christ Jesus (Gal. 3:28). All class and cultural barriers dissolve in the love of Jesus. All racial and social distinctions are obliterated by Jesus’ vicarious work on the cross.

Onesimus is mentioned in Colossians 4:9 as one of the Believers in that city. It may be true, as many manuscripts have it, that Onesimus and Tychicus helped Paul to write Colossians. It may be true that Philemon and his wife and son and Onesimus were all eventually martyred for Christ. It may even be true that this epistle is a document that helped set the stage for the eventual emancipation of slavery. But to focus on these sidebars is to miss the main point.

The book of Philemon demonstrates the mercy of God toward those voted least most likely to succeed. It shows that only Jesus can change one’s relationship to God and to others. When one is converted, their relationship toward God has changed, just as Onesimus’ relationship toward Philemon has changed. Only Jesus makes such a relationship possible. By our Master’s gracious act on Calvary, Onesimus was placed in a new and higher relationship. If he really was a runaway slave, Onesimus could expect just one thing: crucifixion for his sins. Only if he was forgiven could he escape the cross. When one joins God’s family, he is no longer a slave to sin.

So Paul sent Onesimus back with Tychicus with this brief handwritten letter. It was a precaution, for it was safer than Onesimus meeting Philemon alone. Whatever actually happened when Onesimus returned is conjecture. For all our assumptions, it is not known what effect this letter had upon him. However, a main aspect of the story is Onesimus’ assumed restoration to his master’s favor. The point is not Philemon’s actual response to Onesimus, but that a new relationship because of Christ now exists.

What can we suspect was the result of his letter? What was the upshot of the cumulative total of all Paul said and did not say in this epistle? When Paul was freed and knocked at Philemon’s door, did Onesimus answer it, finely dressed like the rest of the family? Did Philemon, Apphia and Archippus rush to the door, have a group hug and thank Jesus together as equals? Everyone likes to think so. But this epistle is not about romanticizing, conjectures, church history or tradition. It is all about potential. It is all about the value of one soul.

Who Onesimus really was is deliberately obscure. Onesimus never says one word in this letter. Paul never quotes him. What could he have said in his own defense?  What could any of us have said standing in Onesimus’ shoes? Truly, we have all been in his shoes. He could represent any one of us, for we are just as guilty and in need of an Intercessor.

This little epistle has been part of God’s Word for twenty centuries because no one seeking Christ can miss its obvious analogies. Martin Luther said it best: “We are all Paul’s Onesimus.” We close the book of Philemon knowing if God can save Onesimus, He can save anyone.



1. Name the city where Paul wrote the Prison Epistles: Colossians, Philemon, Philippians and Ephesians.

2. What does the name “Onesimus” mean?

3. According to verse one, who is in jail with Paul?

4. When Paul wrote to Philemon, he was probably close to 40 years old.  True or False?

5. Name the town where Philemon lived.

6. In this epistle, Paul mentions that Silas is there in prison with him.  True or False?

7. Write a short paragraph on the value of Christian groups meeting in homes, such as the one that met in Philemon’s home.

8. Both Mark and Luke are mentioned in this epistle.  True or False?

9. Name the man Paul sent back with Onesimus.

10. Epaphras is named in v. 23. How does Paul describe this man, both here and in Colossians 1:7 and 4:12?

11. Archippus was most likely the son of:
A. Apphia      
B. Titus        
C. Philemon      
D. Onesimus    
E. both A & C

12. Of all of Paul’s letters, Philemon is the:
A. shortest    
B. most doctrinal    
C. most joyful      
D. most personal  
E. both A & D

13. The epistle to Philemon was written closest to which of the following dates?
A. AD 25-27        
B. AD 33-38      
C. AD 61-63      
D. AD 77-79      
E. AD 90-93

14. From the following list, select the three words which Paul uses in this epistle:
A. Fellowsoldier          
B. Fellowheir          
C. Fellowcitizen
D. Fellowlaborer          
E. Fellowprisoner    
F. Fellowservant
G. Fellowchristian

15. From the following list, select the words that best describe the book of Philemon:
A. Direct      
B. Doctrinal    
C. Cynical    
D. Courteous  
E. Delicate
F. Presumptuous      
G. Gentle  
H. Persuasive  
I.  Aggresive  
J. Harsh

16. What word does Paul use to describe himself in verses 1 and 9?

17. According to verse 16, what change had occurred in the life of Onesimus? 

18. Paul’s wants Philemon to receive Onesimus back as a _________________,  rather than a ________________________.

19. From verses 1, 7, 17 and 19-22, list words and phrases which describe Paul’s relationship with Philemon.

20. Paul lists a number of Philemon’s characteristics in vv. 5-7. List some other attributes that would be necessary for Philemon to receive Onesimus back as a brother in Christ.

21. From the book of Philemon, what can we learn about our personal responsibility to those who are lost?

22. What can be learned from the book of Philemon concerning the need for personal mentoring of new disciples?

23. On a scale from 1-10 (10 being the highest), how would you rate your willingness to invest in the spiritual development of a new Believer?

24. Through your study of Philemon, explain in your own words the difference between tactfulness and manipulation in dealing with another individual.

25. What can you learn about diplomacy from this epistle?

26. If you had to make a personal plea to someone on behalf of another, what can you learn from this epistle that would be helpful in making such a request?

27. List some of the risks one may have to take in mending a broken relationship.

28. Why is it important to include other Believers, as Paul does in verses 1 and 23-24, when you make an appeal on behalf of another?

29. Why do you think Paul does not deal directly with the issue of slavery in this epistle?

30. Why do you think Paul did not insist that Philemon set Onesimus free?

31. Read Col. 3:11 & Col. 3:22-4:1. In what positive ways could Paul’s request change the relationship between a master and his slave or an employer and his employees?

32. List three or four lessons you learned from the book of Philemon.

33. In the allegorical sense of this epistle, we can view Paul as representing Christ’s intercession on our behalf. With this analogy in mind, in what ways do all Believers stand in the shoes of Onesimus?


Maxim of the Moment

A bad husband cannot be a good man.