BUT GOD DEMONSTRATES (gives proof of, renders conspicuous, shows openly) HIS OWN LOVE TOWARD US: sunistesin (3SPAI) de ten heautou agaphen eis hemas o theos: (Ro 5:20; 3:5; Jn 15:13; Eph 1:6, 7, 8; 2:7; 1Ti 1:16)

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But God - He is contrasting the love of man and the love of God. A bold contrast! God did much more than men would ever dare to do by laying down His life for His enemies! Compare this contrast with the other great "but now's" in Romans - Ro 3:21, 6:22, 7:6, 11:30, 16:26 - see notes on  Ro 3:21, 6:22, 7:6, 11:30, 16:26.

Godet writes that...

What man hardly does for what is most worthy of admiration and love, God has done for that which merited only His indignation and abhorrence. (Godet, F L: Commentary on Romans. Kregel. 1998)

James Denney writes that God...

commends, or rather makes good, presents in its true and unmistakable character, His own love toward us... His (emphatic), not as opposed to Christ's (as some have strangely taken it), but as opposed to anything that we can point to as love among men: His spontaneous and characteristic love.  (Nicoll, W Robertson, Editor: Expositors Greek Testament: 5 Volumes. Out of print. Search Google)

Demonstrates (4921) (sunistemi/sunistao from sún = together with + hístemi = set, place, stand) means literally to set, place or put together. To set in the same place, this literal meaning being found in Luke 9:32 (below). To bring together.

When one brings together a person with another person, it is a way of presenting or introducing them. This gives sunistemi the meaning of commend, which means to recommend as worthy of confidence (the implication being that others adopt a similar attitude) or to present to one’s acquaintance for favorable notice. (9/16 NT uses)

Sunistemi can mean to put together by way of composition or combination, to teach by combining and comparing, and hence, make known by action, to demonstrate (to prove or make clear by putting together reasoning or evidence), to show, to prove, to establish, to exhibit. This is the primary meaning in Romans 5:8 (and in Ro 3:5-note) BDAG says the idea is "to provide evidence of a personal characteristic or claim through action". Vine adds that the idea is "to give proof of". It is the act whereby God establishes beyond question the reality of His love.

Finally, sunistemi can mean to put, bring or hold together something in its proper or appropriate place or relationship as when one unites parts into a whole (2Pe 3:5-note). It can convey the idea of to cohere or hold together (Col 1:17-note)

Hodge writes that demonstrate in Romans 5:8 means...

“proves” or “renders conspicuous”. What renders the love of God so especially conspicuous is his sending His Son to die, not for the good, nor even for the righteous, but for sinners, for those who deserve wrath instead of love. (Hodge, Charles: Commentary on Romans. Ages Classic Commentaries  or Logos)

Here are the 16 NT uses of the predominantly Pauline verb sunistemi...

Luke 9:32 Now Peter and his companions had been overcome with sleep; but when they were fully awake, they saw His glory and the two men standing with Him.

Romans 3:5 (note) But if our unrighteousness demonstrates the righteousness of God, what shall we say? The God who inflicts wrath is not unrighteous, is He? (I am speaking in human terms.)

Romans 5:8 (note) But God demonstrates His own love toward us, in that while we were yet sinners, Christ died for us.

Romans 16:1 (note)  I commend to you our sister Phoebe, who is a servant of the church which is at Cenchrea;

2 Corinthians 3:1  Are we beginning to commend ourselves again? Or do we need, as some, letters of commendation to you or from you?

2 Corinthians 4:2 but we have renounced the things hidden because of shame, not walking in craftiness or adulterating the word of God, but by the manifestation of truth commending ourselves to every man's conscience in the sight of God.

2 Corinthians 5:12 We are not again commending ourselves to you but are giving you an occasion to be proud of us, that you may have an answer for those who take pride in appearance, and not in heart.

2 Corinthians 6:4 but in everything commending ourselves as servants of God, in much endurance, in afflictions, in hardships, in distresses,

2 Corinthians 7:11 For behold what earnestness this very thing, this godly sorrow, has produced in you: what vindication of yourselves, what indignation, what fear, what longing, what zeal, what avenging of wrong! In everything you demonstrated yourselves to be innocent in the matter.

2 Corinthians 10:12 For we are not bold to class or compare ourselves with some of those who commend themselves; but when they measure themselves by themselves, and compare themselves with themselves, they are without understanding.

2 Corinthians 10:18 For not he who commends himself is approved, but whom the Lord commends.

2 Corinthians 12:11  I have become foolish; you yourselves compelled me. Actually I should have been commended by you, for in no respect was I inferior to the most eminent apostles, even though I am a nobody.

Galatians 2:18 "For if I rebuild what I have once destroyed, I prove myself to be a transgressor.

Colossians 1:17 (note) And He is before all things, and in Him all things hold together.

2 Peter 3:5 (note) For when they maintain this, it escapes their notice that by the word of God the heavens existed long ago and the earth was formed out of water and by water

There are 15 uses of sunistao/sunistemi in the Septuagint (LXX) (Ge 40:4; Ex 7:19; 32:1; Lev 15:3; Nu 16:3; 27:23; 32:28; Job 28:23; Ps. 39:1; 107:36; 118:27; 141:9; Pr. 6:14; 26:26; Da 7:21)

To reiterate, in Romans 5:8 Paul uses sunistao in the sense of putting together with a view to showing, proving, or establishing. God gives proof of or renders conspicuous His great love for sinners. 

Notice Paul's interesting choice of verb tenses in this verse. In the phrase Christ died for us, died is in the aorist tense indicating a past, action completed on the Cross and thus indicating a historical event which is fixed, objective and unchanging. How natural it would have been, then, for Paul to write: In this historical act, God demonstrated his own love toward us. But instead Paul used the present tense for sunistao/sunistemi  which conveys the idea not of a past tense completed event but an ongoing demonstration of God's love. One could paraphrase it...

God continually demonstrates (present tense - He keeps on showing) His own love toward us. (Comment: In other words God’s love for us is not limited to the past, but has relevance for the present as well. Kenneth Wuest tries to convey this sense rendering it "God is constantly proving His own love to us".)

Leon Morris commenting on Paul's use of the present tense writes that..

The Cross is an event of the past but it keeps showing the love of God. (Morris, L. The Epistle to the Romans. W. B. Eerdmans; Inter-Varsity Press)

His own love toward us - There is extra emphasis for it is not just His love, but His OWN love! Who is "His"? Obviously the Father, not the Son. Sanday & Headlam note that ‘His own love,’ is emphatic, prompted from within not from without."

 Leon Morris offers a beautiful explanation of the significance of His own love writing that...

Paul says that the cross shows us God’s own love. One might expect him to say that the cross shows us the love of Christ. It does that, of course, but own puts the emphasis on the love of the Father (cf. 1John 4:10). “Christ’s action is God’s action. Christ’s love is God’s love” (Nygren). It would be easy to see the cross as demonstrating the indifference of God, a God who let the innocent Jesus be taken by wicked men, tortured, and crucified while he did nothing. And that would indeed be the case were it not that “God was in Christ, reconciling the world to himself” (2Co 5:19). Unless there is a sense in which the Father and Christ are one, it is not the love of God that the cross shows. But because Christ is one with God, Paul can speak of the cross as a demonstration of the love of God. There is no opposition between the Father and the Son in the means of our salvation. (Morris, L. The Epistle to the Romans. W. B. Eerdmans; Inter-Varsity Press)

Romans 5:8 is history’s clearest and greatest “I love you!” Let this certainty of God’s own love give you a new perspective on all aspects of your present life. Such a quality of love is distinctive, unexpected, and unheard of in human relations. As one person has well said the nails could never have kept Jesus on the Cross had love not held Him there!

God's supernatural love is demonstrated irrespective of merit which is totally unlike natural love which is given to those who are lovable. How amazing that God’s love embraces even the unlovely. Natural human love is almost invariably based on the attractiveness of the object of love, and we are inclined to love people who love us. Consequently, we tend to attribute that same kind of love to God. We think that His love for us is dependent on how good we are or on how much we love Him, but such "logic" does not apply to God's love.

What renders the love of God so especially conspicuous is his sending His Son to die, not for the good, nor even for the righteous, but for sinners, who truly deserve wrath not love. Can you see the much more aspect of our salvation here? He didn't save us when we were lovely and lovable but when we were helpless, ungodly sinners which makes our salvation a much more salvation. This quality (and quantity) of divine self-less, undeserved love is completely beyond human comprehension. And yet this is the very love that the just and infinitely holy God had toward us even while we were yet sinners. The God Who hates every sinful thought and every sinful deed nevertheless loves the sinners who think and do those things, even while they are still hopelessly enmeshed in their sin.

Cranfield explains that...

For Paul the death of Christ is the proof of the fact, and the revelation of the nature, of God’s love. (Cranfield, C. E. B Exegetical Commentary on the Epistle to the Romans. Vol 1: Ro 1-8.; Volume 2: Romans 9-16)

Love (26)(agape) describes a love which is foremost an unconditional and sacrificial love. As such it is ultimately a love that God is (1Jn 4:8,16) and that God demonstrates (Jn 3:16, 1Jn 4:9), the supreme demonstration being God's gift of Jesus on the Cross. Agape love seeks the highest good for another no matter what the cost, as demonstrated by Christ’s sacrifice on our behalf. It is therefore not surprising that pagan Greek literature throws little light on the distinctive New Testament meaning of agape love.

Agape love is the love of choice (intentional, volitional, conscious choice), the love of serving with humility, the highest kind of love, the noblest kind of devotion.

Agape love is not motivated by the recipient's appearance, by an emotional attraction, or by a sentimental relationship.

The perfect expression of this sacrificial love on earth is the Lord Jesus Christ for He left heaven, came to earth, took on a human form, was spit on and mocked, was crowned with a crown of thorns, nailed to a cross, abused, and had a spear thrust into His side and yet through all this suffering, His agape love did not waver nor dissipate. He loved the church unto death and that is sacrificial love.

Constable observes that...

Paul here was contrasting the worth of the life laid down, Jesus Christ’s, and the unworthiness of those who benefit from His sacrifice. Whereas people may look at one another as meriting love because they are righteous or good, God views them as sinners. Nevertheless God loves them. His provision of His own Son as our Savior demonstrated the depth of His love (John 3:16). (Expository Notes)

Charles Hodge observed,

“If [God] loved us because we loved him, He would love us only so long as we love Him, and on that condition; and then our salvation would depend on the constancy of our treacherous hearts. But as God loved us as sinners, as Christ died for us as ungodly, our salvation depends, as the apostle argues, not on our loveliness, but on the constancy of the love of God”

IN THAT WHILE WE WERE YET SINNERS CHRIST DIED FOR US: hoti eti hamartolon onton (PAPMPG) hemon Christos huper hemon apethanen (3SAAI): (Is 53:6; 1Pe 3:18; 1Jn 3:16; 4:9,10)

Were (5607) (on) means being and refers to our existence. This verb is in the present tense which indicates our very lifestyle was characterized by sin. We did not simply sin a little here and a little there. Our every thought, word and deed was contaminated by sin.

Yet (2089) (eti) means still and is used here as a function word to indicate the continuance of an action or condition. Leon Morris adds that yet or...

Still points to our state at the time. God did not make some indication that we were ready to amend our lives a precondition of bringing about our salvation. It was for people who had sinned and were still sinners that Christ died. (Morris, L. The Epistle to the Romans. W. B. Eerdmans; Inter-Varsity Press)

Sinners (268) (hamartolos from hamartáno = deviate, miss the mark which some lexicons say is from a = negative + meiromai = attain -- not to attain, not to arrive at the goal) is an adjective (e.g., "that through the commandment sin might become utterly sinful" - see Ro 7:13 -note)  that is often used as a noun (as in this verse and Ro 5:19 [note]) to describe those who are continually erring from the way, constantly missing God's mark, living in opposition to His good and acceptable and perfect will.

Hodge says that the

word sinners expresses the idea of moral wickedness and consequent exposure to divine displeasure. (Ibid)

Hamartolos is translated (NAS) as sinful (3), sinner (12), sinners (31).

Hamartolos is used 47 times in the NAS (Mt. 9:10, 11, 13; 11:19; 26:45; Mark. 2:15, 16, 17; 8:38; 14:41; {note concentrated use in Luke} Lk. 5:8, 30, 32; 6:32, 33, 34; 7:34, 37, 39; 13:2; 15:1, 2, 7, 10; 18:13; 19:7; 24:7; Jn. 9:16, 24, 25, 31; Ro 3:7; 5:8, 19; 7:13; Gal. 2:15, 17; 1Ti 1:9, 15; Heb 7:26; 12:3; James 4:8; 5:20; 1Pe 4:18; Jude 1:15) and 85 times in the Septuagint (LXX) (Ge 13:13; Nu 16:38; 32:14; Deut. 29:19; 1Ki. 1:21; 2Chr. 19:2; Ps 1:1, 5; 3:7; 7:9; 9:16, 17; 10:3, 15; 11:2, 6; 28:3; 32:10; 34:21; 36:11; 37:10, 12, 14, 16, 17, 20, 21, 32, 34, 40; 39:1; 50:16; 55:3; 58:3, 10; 68:2; 71:4; 73:3, 12; 75:8, 10; 82:2, 4; 84:10; 91:8; 92:7; 94:3, 13; 97:10; 101:8; 104:35; 106:18; 109:2, 6; 112:10; 119:53, 61, 95, 110, 119, 155; 125:3; 129:3, 4; 139:19; 140:4, 8; 141:5, 10; 145:20; 146:9; 147:6; Pr 11:31; 12:13; 23:17; 24:19; Is 1:4, 28, 31; 13:9; 14:5; 65:20; Ezek 33:8, 19; Da 12:10; Amos 9:8, 10) Note that in the Septuagint (LXX), hamartolos is frequently used to translate the Hebrew words for wicked or ungodly persons (especially in the Psalms, eg, Ps 1:1 "How blessed is the man who does not walk in the counsel of the wicked [Lxx = hamartolos]").

Hamartolos is used by Homer of missing the mark in shooting. From Homer on it carried the moral sense, "to miss the right, to go wrong, to sin". In the Septuagint it means missing the divinely appointed goal, deviation from what is pleasing to God. A sinner then, is not necessarily one who has gone far astray in wicked living. Rather, every man without Christ is a sinner because he has missed the goal of God's purpose for us as human beings; namely, that we should live holy lives in fellowship with a holy God.

The Jews used hamartolos to describe those who had no respect for Mosaic law or rabbinic traditions and were therefore the most vile and worthless of people.  In their spiritual arrogance the Jews applied hamartolos to the Gentiles to express the contempt in which they held them. And now in the light of the life and death of Christ the Jew discovered himself to be in exactly the same case (under sin - see note Romans 3:9)

The Pharisees felt sinners or hamartolos were inferior because they had no interest in scribal tradition and did not eat food in a state of ceremonial cleanness (see Mark 2:16 "...Why is He [Jesus] eating and drinking with the tax-gatherers and sinners?"). In sum, hamartolos was thus used not only to describe man's natural relationship to God (not hitting His mark) or as a value judgment for a class of people.

In Luke our Lord tells the story of the prideful Pharisee and the humble tax gatherer (noting the irony in the Mark 2:16 passage above that the Jews often grouped tax gatherers with "sinners")...

The Pharisee stood and was praying thus to himself (to whom? "to himself," rather than God, merely congratulating himself on his own self-righteousness and thus received no forgiveness), 'God, I thank Thee that I am not like other people: swindlers, unjust, adulterers, or even like this tax-gatherer. 'I fast twice a week; I pay tithes of all that I get.'

But the tax-gatherer, standing some distance away, was even unwilling to lift up his eyes to heaven, but was beating his breast, saying, 'God, be merciful to me, the sinner!'

I tell you, this man went down to his house justified (acquitted, vindicated, declared righteous) rather than the other; for everyone who exalts himself shall be humbled, but he who humbles himself shall be exalted. (Luke 18:11, 12, 13, 14) (Comment: Paul W. Powell once observed, “Pride is so subtle that if we aren’t careful we’ll be proud of our humility. When this happens our goodness becomes badness. Our virtues become vices. We can easily become like the Sunday School teacher who, having told the story of the Pharisee and the publican, said, ‘Children, let’s bow our heads and thank God we are not like the Pharisee!’“)

A common use of hamartolos in Paul's day is interesting, BDAG explaining that it pertained

to behavior or activity that does not measure up to standard moral or cultic expectations -- being considered an outsider because of failure to conform to certain standards is a freq. semantic component. Persons engaged in certain occupations, e.g. herding and tanning, that jeopardized cultic purity, would be considered by some as ‘sinners’, a term tantamount to ‘outsider’. Non-Israelites were esp. considered out of bounds. (E.g., Gal 2:15 "We are Jews by nature, and not sinners from among the Gentiles") (Arndt, W., Danker, F. W., & Bauer, W. A Greek-English Lexicon of the New Testament and Other Early Christian Literature)

Moulton and Milligan record that hamartolos was frequently found in a common phrase in pagan sepulchral epitaphs in Asia Minor, the epitaph serving as a threat against anyone who would desecrate the tomb. A typical epitaph read “Let him be as a sinner (hamartolos) before the subterranean gods”.

Newell adds that...

"sinning" (hamartolos - sinners) is a stronger word than "strengthless": but it is strong in the wrong direction! Strengthless indeed toward God and holiness, we were all; yet vigorous and active in sin. And what did God do? What does God here say? It was while we were thus sinning that Christ died for us! (Verse by Verse Exposition)

Christ (5547) (Christos from chrio = to rub or anoint as with oil, consecrate or set apart for sacred work) is a transliteration of the Greek word Christos which in turn is used in the Septuagint (LXX) to translate the Hebrew word Messiah or Anointed One. Messiah was a term applied to the OT priests who were anointed with the holy oil, particularly the high priest (Lev 4:3, 5, 16) In the LXX, the prophets are called the anointed of God (LXX = hoi christoi Theou, Ps 105:15). A king of Israel was described upon occasion as “the anointed of the Lord” (LXX = christos tou Kuriou, 1Sa 2:10). In the Gospels the Christ is not a personal name but an official designation for the expected Messiah (see Matthew 2:4, Luke 3:15). As by faith the human Jesus was recognized and accepted as the personal Messiah, the definite article ("the") was dropped and the designation Christ came to be used as a personal name. The name Christ speaks of His Messianic dignity and emphasizes that He is the fulfillment of all the Old Testament promises concerning the coming Messiah (see Messianic Prophecies).

Died (599) (apothnesko from apo = intensifies or means away from +  thnesko = die) is literally to die off, to die a natural death in a sense stronger than thnesko. As noted the aorist tense speaks of a past completed action, and in context is specifically the Crucifixion of Christ, which is not a figment of Paul's but a definite historical event, which in fact constitutes the most profound event in all eternity.

For (5228) (huper) means “for the sake of, in behalf of, instead of.” Click for synopsis of huper used in the NT to convey the idea of substitution.

John uses huper in recording the high priest Caiaphas' "prophecy"

“It is expedient for you that one man should die  instead of (huper) the people, and not that the whole nation perish” (Jn 11:50)

In Galatians 3:13 Paul writes that,

“Christ has redeemed us from the curse of the law, having become a curse  instead of (huper) us.”

Dana and Mantey in their Manual Grammar of the Greek NT say,

In both of these passages the context clearly indicates that substitution is meant.

Thus our Lord died instead of us, taking our penalty, and in behalf of us, in that His death was in our interest.

Notice the downward progression of Paul's description of humanity: "helpless;" "ungodly;" "sinners;" "enemies." The gulf between the preciousness of God's gift and our unworthiness is humanly inconceivable. Only a love way beyond our own would do such a thing. Yet this is exactly what God has done! And he did it for us "while we were yet" this way. He did not extend his love to you only after you turned to him; he extended his greatest gift of love to you even while you were headed the other way (Luke 23:33,34).

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Here is an illustration...They tell the story about a great Russian tribal leader in the early days who had two laws. The first was that all the tribe were to love their parents and the second was they were not to steal. This man's leadership and these laws made his tribe the greatest in all of Russia. Now one day they discovered that someone was stealing. This angered the leader greatly and he brought all the people together. He said, "Let the thief come forward and receive 10 lashes for his crime." No one came and he upped the ante to 20 lashes. Then 30, then 40 lashes. He stopped there for he knew that it would take a strong man to survive 40 lashes with the whip. The crowd dispersed and the leader sent his men to find the thief. Within a week they brought the thief to him and the leader gasped, for the thief was his own mother. The guards were wagering among themselves as to what this great and wise leader would do. Would he keep his word, obey his second law and whip his mother? Or would he obey the first law, love his mother and let her go free, thus disgracing himself and the laws he sought to enforce? If the crime went unpunished, surely everyone would steal. The leader gathered the tribe together. They brought his mother forward and bared her frail back. "Ah, ha," thought the people, "he's going to whip her." Then, just before the whip master brought the whip to bear, the leader strode over to his mother, tearing his shirt off as he went and draped himself over her frail body, taking the 40 lashes himself. That's exactly what Jesus did for us. Jesus took our punishment on the cross. We should have rightly died for our sins, but Jesus took our place. "But God shows his love for us in that while we were yet sinners, Christ died for us."

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C H Spurgeon writes...