Letter writing is a lost art. Texting and tweeting in 140 characters or less has replaced the practice of sitting down with paper and pen and putting into words your thoughts to a friend. And yet, some of the most timeless literature we possess today are simple but powerful letters written by people like Dietrich Bonhoeffer, Martin Luther King, Jr., Bertrand Russell, and Nelson Mandela. Surprisingly, they each wrote from prison, as did the Apostle Paul.


The New Testament includes four prison epistles by Paul, including a short but deeply personal letter he wrote to a friend named Philemon on behalf of a runaway slave named Onesimus. Our next stop on the ultimate road trip through the Bible is a Pauline epistle, which is all about freedom, forgiveness, and second chances. 


Do you need a second chance? Do you need to offer forgiveness and a second chance to somebody who has wronged you? Are you held captive by an unforgiving spirit? With his own hand (1:19), Paul writes one chapter and only twenty-five verses, compelling his friend to receive back a broken but redeemed mutual friend who is profitable to both men. He also teaches an important gospel lesson about God’s grace. 


Philemon is the only private letter Paul wrote that survived among his New Testament epistles. J. Sidlow Baxter describes the brief epistle as a “graceful little masterpiece of fine courtesy, exquisite tact, and even playfulness of wit.” 


The Background Story


Let’s get to know the main characters in Paul’s letter. Who is Philemon? Who is Onesimus? Paul draws Timothy into the already-formed friendship circle and then writes, “To Philemon our beloved fellow worker and Apphia our sister and Archippus our fellow soldier, and the church in your house” (1-2). Paul continues by heaping much praise on Philemon, whom he calls “my brother” (4-7). His affection for his friend ran deep, and what he was about to say to him could put their relationship at risk. 


Most likely, Apphia was Philemon’s wife, and Archippus was their son. They hosted a small congregation in their home, making Philemon a local church leader. Although Paul had never visited Colosse, the city was not far from Ephesus. Philemon and Paul might have become friends during the apostle’s three-year ministry in Ephesus. Archippus appears to have been the pastor at Colosse or nearby Laodicea (Colossians 4:17). 


Paul’s earlier letter to the Colossians suggests that Philemon lived in Colosse and was probably part of the upper class socially and economically. As a wealthy freeman, he owned household slaves, including one named Onesimus. Together, Tychicus and Onesimus carried the epistle to the Colossians from Rome to Colosse (Colossians 4:7-9); they also carried the short, private letter from Paul to Philemon. 


Verse 18 indicates that Onesimus stole money from his master, Philemon, and fled to Rome. By God’s grace and providence, the fugitive met and made friends with Paul, who led Onesimus to faith in Christ. Newly converted, Onesimus quickly grew in God’s grace and became profitable to Paul’s ministry, even while he was in prison. Ironically, the name Onesimus means “useful or profitable.” Paul skillfully uses this idea in his letter to Philemon, saying, “I appeal to you for my child, Onesimus, whose father I became in my imprisonment. (Formerly he was useless to you, but now he is indeed useful to you and to me)” (10-11).


Roman law gave Philemon the authority to invoke the death penalty on Onesimus, his runaway slave. However, on behalf of Onesimus, Paul appeals to Philemon based on their shared brotherhood in Christ. Paul argued that Onesimus’s relationship with Philemon had changed. They were no longer merely master and slave; now, they were both part of the family of God. For that reason, Onesimus was useful and profitable to Philemon. Paul admits that he wanted to keep Onesimus with him in Rome. However, Onesimus rightfully belonged to Philemon. Legally, his fate and future were in his master’s hands, which Paul respected (8-17).


To make the way forward more appealing to Philemon, Paul assumed all of Omesimus’ financial obligations. He writes, “If he has wronged you at all, or owes you anything, charge that to my account. I, Paul, write this with my own hand: I will repay it—to say nothing of your owing me even your own self. Yes, brother, I want some benefit from you in the Lord. Refresh my heart in Christ” (18-20). Paul removed any reason for Philemon to reject his gracious appeal. As quickly as he cleared any damages owed by the runaway slave with an “I owe you” to Philemon, the sly apostle turns the “I owe you” into a “you owe me.”


Paul closes with greetings from five fellow workers in Christ. “Epaphras, my fellow prisoner in Christ Jesus, sends greetings to you, and so do Mark, Aristarchus, Demas, and Luke, my fellow workers” (23-24). These verses provide an important reminder that Christianity is deeply relational and personal. 


We cannot live the Christian life successfully while disconnected from a biblical community of Christ-followers whom we passionately run with as we follow hard after Jesus. Paul mentions these names after already saying how the church met in Philemon’s home. Practicing one’s faith does not get more personal than a small group of people that meet for worship, Bible study, fellowship, and prayer in your own home. Are you part of a small group like that?


On the surface, the principles and applications that arise from this brief visit on the ultimate road trip through the Bible are obvious. Are you deeply drenched in relational Christianity made possible by a local church near you? Is there someone you should forgive, as the Lord has forgiven you? Is there someone like Onesimus in your life who has wronged you and to whom you should extend God’s grace and give a second chance? Paul begins and ends his letter with grace.


Grace to you and peace from God our Father and the Lord Jesus Christ. (3)


The grace of the Lord Jesus Christ be with your spirit. (25)


These are powerful applications to prayerfully consider. But there is more to this brief epistle than what appears on the surface. Before we get to what is less obvious, I must address a question that often arises from Philemon about the Apostle Paul and the institution of slavery in the Roman Empire.


Paul and Slavery


What should we understand about Paul’s view of slavery? If slavery is wrong, why did he not use his apostolic authority to speak against the institution that held between five and ten million humans in bondage throughout the Roman Empire? Does Paul’s silence condone slavery? Foolhardy is the person who thinks that way of Christ’s apostle. 


Had Paul merely railed on slavery like a political activist and called for the freedom of all shackled humans, his words might have shredded society and been lost forever. Instead, Paul offered what the activist cannot: True freedom in Christ. Christianity does more than free slaves; it teaches that slaves and masters are one in Christ. In that way, Paul’s letter to Philemon weakened the institution of slavery and began the abolition of it without the use of political pressure tactics.


Christianity breaks down the damaging hierarchy in social relationships and nullifies worldly rank. For example, faith in Jesus Christ dignifies the slave, emancipates women, and demands social justice for all human beings who are created equally in the image of God. To the Galatians, Paul writes, “There is neither Jew nor Greek, there is neither slave nor free, there is no male and female, for you are all one in Christ Jesus” (Galatians 3:28). A life transformed by Jesus Christ will change social evils and inequities quicker than any law or government program. 


Of course, slavery still exists in parts of our world and is a terrible evil. The thought of one human being owning another is repulsive. Slavery stained the early history of the United States of America, a nation founded upon Judea-Christian values. Today, human trafficking is slavery by another name and tactic. But this present reality does not erase the powerful influence of Christianity and its ability to blunt slavery’s stronghold. As Paul also wrote to the Galatians, “For freedom Christ has set us free; stand firm therefore, and do not submit again to a yoke of slavery” (Galatians 5:1). 


The Gospel According to Philemon


Now, back to what is perhaps less obvious in Paul’s letter to Philemon. I call it the gospel according to Philemon. What do I mean by that? Let’s start with an observation made by Martin Luther, the Roman Catholic monk who sparked the Protestant Reformation. He correctly said, “We are all Onesimuses!” Onesimus was a runaway cracked pot, broken by the cruelty of Roman slavery plus his poor personal choices that led to thievery. Romans 3:23 summarizes the human condition, “For all have sinned and fall short of the glory of God.”


Like Onesimus, we are sinners who fall short of God’s holy standard, which is the bad news we must all embrace before the Gospel becomes good news. But the bad news gets worse. Also, like Onesimus, the death penalty awaits us. Romans 6:23a says, “The wages of sin is death.” 


Furthermore, like Onesimus, someone else paid the penalty for our sin, and that’s good news! Paul said to Philemon, “If he has wronged you at all, or owes you anything, charge that to my account” (18). 


Through Christ’s substitutionary death upon the cross, our Savior paid the penalty for our sin and purchased our redemption. Second Corinthians 5:21 says, “For our sake he made him to be sin who knew no sin, so that in him we might become the righteousness of God.” And in the same way that Paul played the mediator between Onesimus and his owner, Philemon, Jesus Christ is the only mediator between God and man (1 Timothy 2:5). 


Finally, believers in Jesus Christ are no longer slaves to sin but slaves to righteousness. Romans 6:17-18 says, “But thanks be to God, that you who were once slaves of sin have become obedient from the heart to the standard of teaching to which you were committed, and, having been set free from sin, have become slaves of righteousness.” More so, by faith, we are brothers and sisters in Christ, siblings in the family of God (15-16).


How glorious is the Gospel according to this brief letter to Philemon! In Christ, we are set free from the penalty and power of sin, forgiven, and given a second chance to live for God. Seize the moment and place your faith in Jesus Christ right now. And if you already possess the gift of eternal life, share the good news with someone else by writing them a personal letter today.

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“Every detail in our lives of love for God is worked into something good.”

Romans 8:28 MSG