Paul expects that his imprisonment will not end in shame (v. 18b-20). Paul’s desire is to be free of this legal threat, to be delivered from the charges and return to the ministry to which he has been called.
Paul’s expectation is that everything that has happened will turn out to be his salvation. The word here is used literally for getting out of a boat (John 21:9, ἀποβαίνω). The word comes to be used as a metaphor for getting an expected result: “things turn out as planned.” “Deliverance” is usually translated salvation, the word does not always mean “salvation from my sins,” sometimes it means “saved from a bad situation.” “Eager expectation” (ἀποκαραδοκία) is a rare word only found in Christian writings, although the verb appears in Herodotus for “awaiting the outcome of a war” (vii.163, 168). Paul used the word in Rom 8:19: all creation has an “eager expectation for revealing of the sons of God.” The impression the reader has is of Paul looking forward to his release so that he can return to his long-delayed mission.
Being under house arrest is something most people in the Roman world would consider “shameful.” Shame in the Roman world was serious, people would do all that they could to avoid something that brought them shame awhile at the same time trying to increase their honor in society. This pursuit of honor often took precedence over wealth or love. Just to be under house arrest for any reason was shameful. To be in prison for preaching the story of a man who was crucified (the ultimate shame) would be enough shame to doom most people.
Yet Paul He has “full courage” that “Christ will be honored in my body,” implying that things might not go as well as he hopes. Even if he should die as a result his trial, death is still a gain! (v. 21-24) This is one of the most cherished passages in Philippians because it expresses the hope that when we die, we will be with Christ, which is “far better.” Paul’s life is defined as “Christ.” Whatever he does in this life is for Christ and Christ alone. Roman life was defined by their pursuit of honor. Whatever a Roman might do in order to gain honor for themselves, yet Paul willingly gives up in order to reach others for Christ.
“To die is gain” runs counter to how a Roman person would think. If Paul dies, then he proves his shame! Many famous Romans chose to commit suicide rather than accept greater shame, “death before dishonor.” Socrates is an example of this, although much closer to the time of Paul Cato the Younger killed himself in 46 B.C. because his army was defeated by Julius, so too Brutus, who killed himself in 42 B.C. after it was obvious Octavian would prevail (Brutus participated in the assassination of Julius, Octavian’s adopted father). Both Seneca and Nero killed themselves a few years after Philippians was written (A.D. 65 and 68).
This anticipates what Paul will say about Jesus in the next chapter. Jesus is the ultimate example of “to die is gain.” Paul is not talking about a “noble suicide.” Just as Jesus gave his life on behalf of others, Paul is also willing to lay down his life so that the Gospel will continue to advance.
Paul is “hard pressed” between these two good things. If he lives, he can continue the ministry to which God has already called him, especially to continue working with the Philippian church in order to build it up spiritually. Paul is not expressing some sort of morose acceptance of his impending death, nor is he giving up on this life because of his hardships. If he is not executed, he will continue his mission; if he is executed God has already raised up other leaders who will continue to preach the Gospel.
Because he expects the gospel to continue to advance, he prays for the Philippian church to continue to grow spiritually (v. 25-26). In spite of his imprisonment and competition of rival preachers, all that matters to Paul is the Gospel of Jesus Christ.