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Therefore, I hope to send him as soon as I see how things go with me; (Philippians 2:23)
Because of what Paul has just told them (verses 19-22), Paul was confident that he would be sending Timothy to inform them of how things went with him and inquire about their situation. The Greek word (πέμπω pempō) carries with it a different connotation than apostello. The latter term tends to mean someone sent by one who has the authority to send him or her, while the former carries the idea of someone willingly going.
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As soon as I see how things go with me. Again, Paul was currently imprisoned in Rome, and no one knew for sure whether he would be condemned or acquitted. He had been released from the first trial. (2 Tim. 4:16) He at least knew that he had Timothy, one of his most trusted fellow workers, which he would soon send to the congregation in Philippi. If he was condemned and executed, he knew that he could trust Timothy to finish the work that he had started. The experience that Timothy gained by working with Paul even up to this point (60-61 C.E.), some ten years was priceless and trained him to be competent and skilled, so that he could take on special assignments himself, being a man in whom the apostle Paul had great trust. However, if he was acquitted, Paul would be released and could go on caring for the congregations that he had started throughout the Roman Empire.
 Albert Garner, The Prison Epistles (Verse by Verse) (Lakeland, Florida: The Blessed Hope Foundation, 1977). Page 161. W. E. Vine, Merrill F. Unger and William White, Vine’s Complete Expository Dictionary of Old and New Testament Words (Nashville, Tennessee: Thomas Nelson, Inc., 1996). Page 560, Send #2 Notes.