Thoughts on Philemon

What Train are you on?

It’s imperative to listen . . . when a man writes from prison, or a dying man preaches his last sermon.

Paul wrote his letter to Philemon from his favorite writing office, a Roman prison cell.

Philemon and Onesimus It's all about second chances.

“God of new beginnings, here I am again.”

“I’m so thankful God is a God of second chances.”  – testimony at Dry Creek Bible Conference

“Fall down seven times , get up eight.”


Logan Skiles, a modern day Paul, preached one of his last sermons from Philemon.  It was August 30, 1995.  He would be dead from cancer within three weeks.


I notated Bro. Skiles’ words in my Bible,   “Don’t give up on anyone.”

"Don't give up on anyone." Notes from Logan Skiles' sermon 8-30-95

That is the theme of the shortest book of the Bible.

25 verses on second chances,

new starts,


and redemption.

It’s about a wonderful word called reconciliation.

In verse 1, Paul begins his letter with a telling statement,   “Paul, a prisoner of Christ Jesus . . .”

In other greetings, Paul calls himself an apostle or servant.  In the sister book of Colossians (scholars believe both letters were written together and carried together to Colossae.) it’s “Paul, an apostle.”

But in Philemon, it’s a prisoner…

Paul realized who he was… a prisoner

Not of the Roman empire.

He knew whom he belonged to.

His ownership deed was clear.

He belonged to Jesus.  That’d been settled on the dusty road from Jerusalem to Damascus a  lifetime ago.

Charles Swindoll, in his wonderful new book,  Speaking Well, says a successful speaker must:

  • 1. Know who he is.
  • 2.   Accept who he is
  • 3.  Be comfortable with who he is.

That’s a good list for anyone.

The Apostle Paul understood this.

“Paul,  a prisoner of Christ Jesus…”    He knows who he is and has comfortably accepted it.


My mother’s family were railroad people for generations.

I’ll put Paul’s confidence in “who he was “ in railroad terminology:

 1.  He knew what train he was on.

2.  He knew who was driving the train.

3. He knew where the train was going.

  •  First,  he was on the Jesus train.  Everything about his life was tied up in his intimate relationship with Jesus.  Paul had went from a killer of Christian’s to the world’s best known advocate of the same.
  •  Secondly, he knew who the engineer was.  It’s stated clearly in verse 1,  “Paul, a prisoner of Christ Jesus.”

Sounds pretty clear to be.  Paul was a passenger but not the driver.

  •  Finally, he was sure where the train was going.  This is intertwined with knowing what train and who’s driving it.


Paul’s confidence in the train’s destination is found in his final recorded written words,

“The Lord will rescue me from every evil attack and will bring me safely to his heavenly kingdom.”      II Timothy 4:18

The Roman chopping block wasn’t Paul’s final destination.  His train was heading to Heaven.


As we begin looking at these twenty-five verses one by one, let’s be clear.  It’s written by a man who had his act together.

It’s a letter about second chances and human persuasion.


Next we’ll examine Paul’s lesson in building rapport before making a request.

In verses 1-7, he lays a strong foundation before he “lowers the boom” on Philemon.




Curt Iles




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