If I tell you, “I am not unhappy,” in most context, it means I am very happy. Of course, the context is always important. “I am not scared.” Means I feel very brave in the face of what might seem scary. This figure of Speech occurs many times in scripture also and serves to emphasis the positive of the idea being made. Romans 4:19 speaks of Abraham, “Without becoming weak in faith” which means “remained strong in faith.” This is why Abraham is included in the Hall of Faith of Hebrews 11. He was not neutral in his faith, but strong.
I want to turn our attention to the phrase “not ashamed.” This phrase is used eight times in the Bible. There are other times when there are a few words between the words “not” and “ashamed” with the same affect. It will suffice to stick with the cases of “not ashamed.” When this phrase is understood in terms of this figure of speech it usually means something like “proud.” The first verse appears in Genesis.
Genesis 2:25 And the man and his wife were both naked and were not ashamed.
What a verse to start with. Was Adam and Eve proud to be naked? It is possible to think that they, being in their time of innocence before the fall, were proud of their God given suites; However, the context shows it seems to be just stating the fact that they felt no shame at that time. So, the figure of speech does is not used in this verse.
Job 19:3 “These ten times you have insulted me; You are not ashamed to wrong me.
Here Job is addressing his friends. They believe Job has done some awful sin to cause God to be so upset with him. They are “not shy” about telling him and in so doing, insult Job. They feel it is their place to shame Job so he will repent of his sin. They are proud to be in a such righteous position that they can tell Job these things. They are proud to tell Him what he has done wrong. All the while Job knows he is innocent of all these things. This figure of speech does turn “not ashamed” into proud with an emphasis. “You are certainly proud” or “definitely proud to wrong me.”
Jeremiah 8:12 “Were they ashamed because of the abomination they had done? They certainly were not ashamed, And they did not know how to blush; …
We have a strong “certainly were not ashamed.” The context has this phrase as in response to the question, “Were they ashamed” and follows the response with “they did not know how to blush.” Here the focus is on their lack of shame where one would expect the to have shame for their idolatry. So, the figure is probably not used in this verse.
Romans 1:14–17 - 14 I am under obligation both to Greeks and to barbarians, both to the wise and to the foolish. 15 So, for my part, I am eager to preach the gospel to you also who are in Rome. 16 For I am not ashamed of the gospel, for it is the power of God for salvation to everyone who believes, to the Jew first and also to the Greek. 17 For in it the righteousness of God is revealed from faith to faith; as it is written, “BUT THE RIGHTEOUS man SHALL LIVE BY FAITH.”
Verse 16 is a powerful one that is familiar to many people. It is worth while reading verse 14-17 to get a more complete context. Paul says he is eager to preach the gospel in Rome. His reason being, “I am not ashamed of the gospel” and the reason for that is because “it is the power of God for salvation to everyone who believes.” Is Paul just “not ashamed” or is he proud of the Gospel. Yes, he is proud of the Gospel. When most people read “I am not ashamed of the gospel” they say to themselves, “I don’t want to be ashamed.” Ministers ask, “Are you ashamed?” When the real question is “Are you proud of the Gospel?” Paul is. I am.” We can say, “We are proud of the gospel, for it is the power of God …”. The figure of lessening a negative to emphasis the positive applies here.
2 Timothy 1:12 For this reason I also suffer these things, but I am not ashamed; for I know whom I have believed and I am convinced that He is able to guard what I have entrusted to Him until that day.
Here again the context shows the figure of speech is applied. In this verse the context shows Paul expects his confidence in Christ to be validated. There will be no disappointment in the confidence he places in Christ. Paul suffers as a prisoner but without a sense of loss. John the Baptist seemed to have wavered in his confidence, but Paul who has seen Christ has full confidence.
2 Timothy 1:16 -17 The Lord grant mercy to the house of Onesiphorus, for he often refreshed me and was not ashamed of my chains; but when he was in Rome, he eagerly searched for me and found me
If Onesiphorus was around Paul much, Paul’s enthusiasm for the Gospel and the Lord’s work surely rubbed off onto him also. Whether He was simply not affected by Paul’s chains (neutral) or proud (positive) of how God was using this “prisoner” may not be clearly definable, but I suspect he was proud of Paul’s chains.
Hebrews 2:11 For both He who sanctifies and those who are sanctified are all from one Father; for which reason He is not ashamed to call them brethren,
Jesus who sacrificed his life for us is proud to call us brethren. Along with all Christ has done for us he is “proud” to consider us family.
Hebrews 11:16 But as it is, they desire a better country, that is, a heavenly one. Therefore God is not ashamed to be called their God; for He has prepared a city for them.
Referring to those of the Hall of Faith, God is proud to be called their God because they desired a heavenly home prepared for them by God.
The negation of a negative word occurs often in the Bible. When you see one, take pause to consider if it is a figure of speech that makes it an emphasized positive. If so, maybe it is time for a note in the margin.
The figure of speech discussed is tapeinosis (Ta-pei-nō´-sis). In this figure “the thing that is lessened is the same thing which is increased and intensified.”
All scripture quotation is from the NASB95 unless otherwise indicated.
 Bullinger, E. W. (1898). Figures of speech used in the Bible (p. 159). London; New York: Eyre & Spottiswoode; E. & J. B. Young & Co.