AND THE GIFT IS NOT LIKE THAT WHICH CAME THROUGH THE ONE WHO SINNED FOR ON THE ONE HAND THE JUDGMENT AROSE FROM ONE TRANSGRESSION RESULTING IN CONDEMNATION: kai ouch os di enos hamartesantos (AAPMSG) to dorema to men gar krima ex enos eis katakrima:  (Ge 3:6-19; Gal 3:10; Ja 2:10)

S Lewis Johnson in light of some deep doctrinal teaching which might lose us, reiterates that...

The master-thought of the section is the unity of the many in the one. In Adam's case it is the unity of the many in a representative who fell. In Christ's case it is the unity of the many in a representative who overcame, including in His victory all who are in Him. (Romans 5:15-21)

J Vernon McGee adds this thought...

Now I recognize that this is a difficult section, and this is one of the most difficult passages. To simplify it, all this section means is this: one transgression plunged the race into sin; and one act of obedience and the death of Christ upon the cross makes it possible for lost man to be saved. (McGee, J V: Thru the Bible Commentary:  Thomas Nelson or Logos)

Recall that there are 3 major contrasts in verses Romans 5:15, 16 and 17...

(Romans 5:15) Adam's Transgression versus Christ's Free Gift.

(Romans 5:16) Adam's Sin Brought Judgment and the verdict rendered was "Condemned". Christ's Death Brought Justification - the contrast then is condemnation in Adam and justification in Christ. When Adam sinned, he was declared unrighteous and condemned. When a sinner trusts Christ, he is justified—declared righteous in Christ.

(Romans 5:17) Because of Adam's Sin, Death reigned. Those Who Receive Christ Reign in Life.

Romans 5:16 is explains how Adam and Christ are not alike demonstrating that there is no comparison between the grace of God in Christ and the offense of Adam and its sinister consequences. In Romans 5:16 we see 4 contrasts as shown in the table below.

The (free) gift - Paul extends his first statement about the free gift that was just mentioned in the first clause of Romans 5:15 (note). What is the free gift? From the context it equates with the gift of righteousness (see note Romans 5:17 "the gift of righteousness will reign") in and through Jesus Christ. Adam's sin had consequences (his "gift") for the entire human race in that many died. Jesus provides a gift that also has consequences for the entire human race, but there is a difference.

Ironside explains that...

There is a difference as to the offense and the gift however. Adam's one offense involved his race in the consequences of his fall. Christ, having satisfied divine justice, offers the gift of life by grace to all who will believe and so it abounds to many.

MacDonald adds a note on this difference writing that...

The free gift of Christ dealt effectively with many offenses, not just one, and resulted in the verdict “Acquitted.” Paul highlights the differences between Adam’s sin and Christ’s gift, between the terrible havoc wrought by one sin and the tremendous deliverance wrought from many sins, and finally between the verdict of condemnation and the verdict of justification. (MacDonald, W & Farstad, A. Believer's Bible Commentary: Thomas Nelson or Logos)

Vine says that...

This second contrast is one of quality. Condemnation was passed as a result of one trespass; justification is declared in regard to many trespasses. (Vine, W. Collected writings of W. E. Vine. Nashville: Thomas Nelson or Logos)

S Lewis Johnson explains it this way...

The gift of God cannot be compared with the sin of Adam, Paul says. In the case of Adam there were many offences, and they led to judgment and condemnation. In the case of Christ there is the free gift of righteousness that has come from any offences and their satisfaction by the sacrificial blood of the Redeemer. The judgment came from one deed, but God's gift is His answer to a multitude of misdeeds, the accumulated sins of the centuries since Adam. (Romans 5:15-21)

John Murray notes that...

The one trespass demanded nothing less than the condemnation of all. But the free gift unto justification is of such a character that it must take the many trespasses into its reckoning; it could not be the free gift of justification unless it blotted out the many trespasses. Consequently, the free gift is conditioned as to its nature and effect by the many trespasses just as the judgment was conditioned as to its nature and effect by the one trespass alone” (The Epistle to the Romans  Eerdmans, 1965)

Gift (1434) (dorema from dorea = free gift with emphasis on gratuitous nature + --ma = the result of giving [dosis]) is the thing given or that which is granted. Dorema is used only in one other passage...

Every good thing bestowed and every perfect gift (dorema) is from above, coming down from the Father of lights, with whom there is no variation, or shifting shadow. (James 1:17)

The one who sinned - Adam. One sin by this one man brought God's judgment and condemnation.

Sinned (264) (hamartano) means to miss the mark and so to miss God's will and purpose for one's life. The aorist tense means that at one point in time Adam sinned. Adam’s one transgression brought death. Jesus’ death brought forgiveness for thousands of transgressions. Clearly, Jesus’ work is far superior.

Judgment (2917) (krima from kríno = to judge; suffix –ma indicates result of judging) denotes the result of the action signified by verb krino and thus is a judicial sentence from the magistrate. It is the sentence pronounced, the verdict, the act of judging. Krima signifies judgment carried out.

Barnes writes that krima means...

The sentence; the declared penalty. The word expresses, properly, the sentence which is passed by a judge. Here it means the sentence which God passed, as a judge, on Adam for the one offence, involving himself and his posterity in ruin, Ge 2:17; Ge 3:17-19. (Albert Barnes. Barnes NT Commentary)

One transgression - Transgression is added by the translators.

Condemnation (2631)(katakrima from katá = against, down + kríno = basic meaning was "to separate" from which the idea of discriminate, distinguish, and then to judge or pronounce sentence against) literally is judgment coming down on someone. Katakrima means to judge someone as definitely guilty and thus subject to punishment, which accounts for the literal translation of "adverse judgment and resultant punishment". It is a legal technical term for the result of judging, including both the sentence and the execution or the sentence followed by a suggested punishment (The suffix -ma makes it the result of judgment). Katakrima is always an adverse verdict. Stated another way, katakrima (condemnation) relates to the sentencing for a crime, but its primary focus is not so much on the verdict as on the penalty that the verdict demands.

The divine guilty verdict is the polar opposite of justification. The verdict refers to God’s sentence. The word for condemnation involves the ideas of “punishment” and “doom.” So we ask: Condemned to what? The answer is, to divine punishment and doom. The seriousness of this condemnation cannot be overstated.

Regarding condemnation MacDonald reminds us that...

Man is condemned on three grounds: He has a sinful nature, Adam’s sin is imputed to him, and he is a sinner by practice. But his crowning guilt is his rejection of the provision which God has made for his salvation (John 3:18, 19, 36). (MacDonald, W., & Farstad, A. Believer's Bible Commentary: Old and New Testaments. Nashville: Thomas Nelson)

BUT ON THE OTHER HAND THE FREE GIFT AROSE FROM MANY TRANSGRESSIONS RESULTING IN JUSTIFICATION: to de charisma ek pollon paraptomaton eis dikaioma: (Isa 1:18; 43:25; 44:22; Lu 7:47-50; Acts 13:38,39; 1Co 6:9-11; 1Ti 1:13-16)

But on the other hand - The UBS Handbook rightly observes that "At this point the analogy with Adam breaks down. After his one sin came the judgment of “Guilty”; but after so many sins comes the undeserved gift of “Not guilty!” In this way Paul demonstrates the superiority of God’s grace over Adam’s sin. Grace had a much more difficult road to travel than sin had. To use an illustration from everyday life, it is much easier for an infection to spread than it is to cure the infection once it has spread throughout the body." (Ref)

Free gift (grace gift) (5486) (charisma [see word study] from charis [see word study on charis] = grace + the ending --ma which indicates the result of something, in this case the result of grace) is a gift of grace or an undeserved benefit. It refers something given by God completely apart from human merit. Note that God is the Giver in 16/17 NT uses charisma

In Romans, Paul uses charisma in reference to the gift of salvation (Romans 5:15-16; note on Ro 6:23), the blessings of God (notes on Romans 1:1, Romans 11:29), and divine enablements for ministry (note on Romans 12:6). Every other use of the word by Paul, and the one by Peter (see note 1 Peter 4:10-13), relates it to the divine enablements for believers to minister in the power of the Holy Spirit.

Transgressions (3900) (paraptoma from parapipto = fall aside from para = aside + pipto = fall) (see use in Romans 4:25) means a falling beside, deviation from a path or departing from the norm. By extension, it carries the idea of going where one should not go, and therefore is sometimes translated “trespass”. Here  the trespass is eating "from the tree of the knowledge of good and evil" Genesis 2:17. The picture is that of one who stumbles or falls. The idea conveyed by transgression is that one has crossed a line, challenging God's boundary, whereas the idea behind sins (hamartia 266) is missing a mark, specifically God's perfect, holy standard.

Now the contrast turns to condemnation in Adam and justification in Christ. Not only is our guilt derived from one man’s sin, but it is derived from only one sin of that man. It is not the sins of Adam’s lifetime that have been imputed to us, but only his original sin. That one sin brought condemnation. However, the righteousness which is imputed to us by Christ, through the free gift of God’s grace, covers not just that one offense but many offenses.

Justification  (1345) (dikaioma from dikaióo = to justify <> díkaios = just, righteous <> dike = right) refers to what God has declared to be right and here referring to His decree of retribution which has the force of law. Dikaioma is used elsewhere in this Epistle with its other meaning of “righteousness” (see table below).   Strictly speaking dikaioma is what God establishes as just.  Dikaioma is used in this verse to signify the clearing of one of a violation as an act of justification and equates with the removal of guilt or granting of an acquittal.

Adam brought upon all men the condemnation for only one offense—his willful act of disobedience. Christ, however, delivers the elect from the condemnation of many offenses.

Morris comments that...

The one sin of Adam had as its end result condemnation for all the race, but Christ’s act of justification was also far-reaching. It was concerned with more than the one sin of Adam. The believer finds pardon not only for the one sin he shares in Adam, but for all his other sins as well. (Ibid)

William Newell explains that Romans 5:16...

tells us that out of Adam's one trespass came judgment, but that out of many trespasses laid upon Christ came not judgment, but a righteous act (dikaioma). In short, all men acted, -sinned in Adam's act of sin. (Romans 5)

John MacArthur adds that Romans 5:16 has two very practical truths...

The first is that God hates sin so much that it took only one sin to condemn the entire human race and separate them from Him. It was not that Adam’s first sin was worse than others he committed or worse than men have committed since. It was simply that his first sin was sin. At the time, eating the forbidden fruit was the only sin that Adam and Eve could have committed, because God had placed but one restriction on them. But had it been possible, any other sin would have had the same effect. In the same way, any sin that any man has ever committed would be sufficient to damn the whole human race, just as Adam’s one sin did. A sobering thought, indeed.

The other truth in verse 16 is still more amazing and incomprehensible, and is as heartening as the first is sobering. Greater even than God’s hatred of sin is His love for the sinner. Despite the fact that God hates sin so much that any one sin could damn the human race, His loving grace toward man is so great that He provides not only for the redemption of one man from one sin but for the redemption of all men from all sins. Jesus Christ took upon Himself the sins of the whole world. “God was in Christ reconciling the world to Himself, not counting their trespasses against them” (2 Cor. 5:19). (MacArthur, J: Romans 1-8. Chicago: Moody Press or Logos)

John Piper has a pragmatic comment on Romans 5:16...

First the minor point: Notice, in the last half of the verse, that the "free gift," which is the "gift of righteousness," according to verse 17, "results in justification." "The free gift arose from many transgressions resulting in justification." This is crucial because it shows that there is a foundation for justification, namely, "the gift of the righteousness" of Christ, or, as verse 18 calls it, "the one act of righteousness," or, as verse 19 calls it, "the obedience of the One." Justification is not merely a new relationship with God, or a new status before God, hanging in the air. It is a new legal standing on the basis of Christ's righteousness, or Christ's obedience. That is the minor point in verse 16 – a huge minor point – "the free gift results in justification." "The free gift" is not itself justification; it is the foundation of justification. We are declared righteous on the basis of the free gift of righteousness – Christ's "righteousness" (verse 18), Christ's "obedience" (verse 19).

When you read the gospels and you see your Lord living out a perfect life of righteousness, rejoice that he not only is giving you an example of how to live, but he is also laying the foundation for your acceptance with God by grace through faith alone.

God's Grace Triumphs Over Many Transgressions, Not Just One

Now what is the major point of verse 16? What is the contrast that Paul sees between the work of Christ and the sin of Adam? He says, "The gift is not like that which came through the one who sinned." So we know he is still talking about how Adam and Christ are not alike. The next clause gives us the explanation:

"For on the one hand the judgment arose from one transgression resulting in condemnation, but on the other hand the free gift arose from many transgressions resulting in justification."