Ward Fenley
I was once asked this question concerning the old and new wineskins:

 I read in Luke 5:36-39 and correct me if I'm wrong.  Jesus says:

 5:36 And he spake also a simile unto them -- `No one a patch of new  clothing doth put on old clothing, and if otherwise, the new also doth  make a rent, and with the old the patch doth not agree, that [is] from  the new.
 5:37 `And no one doth put new wine into old skins, and if otherwise,  the  new wine will burst the skins, and itself will be poured out, and the  skins will be destroyed;
 5:38 but new wine into new skins is to be put, and both are preserved  together;
 5:39 and no one having drunk old [wine], doth immediately wish new,  for  he saith, The old is better.' (YLT).

 Was Jesus refering to the Old Covenant which had to be put aside and replaced with the New Covenant?  In other words, New Covenant Theology?

It seems to me that Christ was addressing the problem that would be so prevalent among the first-century professing Christians: their attempt to add works to Christ for salvation. Here are some passages that come to mind:

Galatians 1:6-7  I marvel that ye are so soon removed from him that called you into the grace of Christ unto another gospel: {7} Which is not another; but there be some that trouble you, and would pervert the gospel of Christ.
Galatians 2:4-6  And that because of false brethren unawares brought in, who came in privily to spy out our liberty which we have in Christ Jesus, that they might bring us into bondage: {5} To whom we gave place by subjection, no, not for an hour; that the truth of the gospel might continue with you. {6} But of these who seemed to be somewhat, (whatsoever they were, it maketh no matter to me: God accepteth no man's person:) for they who seemed to be somewhat in conference added nothing to me:
Galatians 2:17-21  But if, while we seek to be justified by Christ, we ourselves also are found sinners, is therefore Christ the minister of sin? God forbid. {18} For if I build again the things which I destroyed, I make myself a transgressor. {19} For I through the law am dead to the law, that I might live unto God. {20} I am crucified with Christ: nevertheless I live; yet not I, but Christ liveth in me: and the life which I now live in the flesh I live by the faith of the Son of God, who loved me, and gave himself for me. {21} I do not frustrate the grace of God: for if righteousness come by the law, then Christ is dead in vain.
Galatians 3:1-5  O foolish Galatians, who hath bewitched you, that ye should not obey the truth, before whose eyes Jesus Christ hath been evidently set forth, crucified among you? {2} This only would I learn of you, Received ye the Spirit by the works of the law, or by the hearing of faith? {3} Are ye so foolish? having begun in the Spirit, are ye now made perfect by the flesh? {4} Have ye suffered so many things in vain? if it be yet in vain. {5} He therefore that ministereth to you the Spirit, and worketh miracles among you, doeth he it by the works of the law, or by the hearing of faith?
Galatians 4:7-11  Wherefore thou art no more a servant, but a son; and if a son, then an heir of God through Christ. {8} Howbeit then, when ye knew not God, ye did service unto them which by nature are no gods. {9} But now, after that ye have known God, or rather are known of God, how turn ye again to the weak and beggarly elements, whereunto ye desire again to be in bondage? {10} Ye observe days, and months, and times, and years. {11} I am afraid of you, lest I have bestowed upon you labour in vain.
Galatians 4:17-21  They zealously affect you, but not well; yea, they would exclude you, that ye might affect them. {18} But it is good to be zealously affected always in a good thing, and not only when I am present with you. {19} My little children, of whom I travail in birth again until Christ be formed in you, {20} I desire to be present with you now, and to change my voice; for I stand in doubt of you. {21} Tell me, ye that desire to be under the law, do ye not hear the law?
Galatians 5:2-12  Behold, I Paul say unto you, that if ye be circumcised, Christ shall profit you nothing. {3} For I testify again to every man that is circumcised, that he is a debtor to do the whole law. {4} Christ is become of no effect unto you, whosoever of you are justified by the law; ye are fallen from grace. {5} For we through the Spirit wait for the hope of righteousness by faith. {6} For in Jesus Christ neither circumcision availeth any thing, nor uncircumcision; but faith which worketh by love. {7} Ye did run well; who did hinder you that ye should not obey the truth? {8} This persuasion cometh not of him that calleth you. {9} A little leaven leaveneth the whole lump. {10} I have confidence in you through the Lord, that ye will be none otherwise minded: but he that troubleth you shall bear his judgment, whosoever he be. {11} And I, brethren, if I yet preach circumcision, why do I yet suffer persecution? then is the offence of the cross ceased. {12} I would they were even cut off which trouble you.
Galatians 6:12-15  As many as desire to make a fair show in the flesh, they constrain you to be circumcised; only lest they should suffer persecution for the cross of Christ. {13} For neither they themselves who are circumcised keep the law; but desire to have you circumcised, that they may glory in your flesh. {14} But God forbid that I should glory, save in the cross of our Lord Jesus Christ, by whom the world is crucified unto me, and I unto the world. {15} For in Christ Jesus neither circumcision availeth any thing, nor uncircumcision, but a new creature.
What I see is that the enormous danger to which Paul is referring is the apostasy among professing Christians. After having received the holy commandment to trust Christ alone for the salvation from the eternal punishment and wrath of God, some of these were being drawn back to trusting in law plus Christ. "Riches" were often how works were described:
James 5:1-3  Go to now, ye rich men, weep and howl for your miseries that shall come upon you. {2} Your riches are corrupted, and your garments are motheaten. {3} Your gold and silver is cankered; and the rust of them shall be a witness against you, and shall eat your flesh as it were fire. Ye have heaped treasure together for the last days.
Most people interpret these passages as referring to boats, houses, cars, etc. But that is not at all to what James is referring. Nor was
Jesus referring to these when He said:
Matthew 6:16-24  Moreover when ye fast, be not, as the hypocrites, of a sad countenance: for they disfigure their faces, that they may appear unto men to fast. Verily I say unto you, They have their reward. {17} But thou, when thou fastest, anoint thine head, and wash thy face; {18} That thou appear not unto men to fast, but unto thy Father which is in secret: and thy Father, which seeth in secret, shall reward thee openly. {19} Lay not up for yourselves treasures upon earth, where moth and rust doth corrupt, and where thieves break through and steal: {20} But lay up for yourselves treasures in heaven, where neither moth nor rust doth corrupt, and where thieves do not break through nor steal: {21} For where your treasure is, there will your heart be also. {22} The light of the body is the eye: if therefore thine eye be single, thy whole body shall be full of light. {23} But if thine eye be evil, thy whole body shall be full of darkness. If therefore the light that is in thee be darkness, how great is that darkness! {24} No man can serve two masters: for either he will hate the one, and love the other; or else he will hold to the one, and despise the other. Ye cannot serve God and mammon.
You cannot serve works and God. The context is clearly addressing the Pharisees who desired to be seen for their good deeds (menstrual rags according to Isaiah).

To try to combine works with Christ is like putting new wine into old wineskins. The tear is made even worse because of the greater punishment and accountability for hearing the glorious Gospel of the blessed God. Peter alludes to this more intense accountability:

2 Peter 2:18-22  For when they speak great swelling words of vanity, they allure through the lusts of the flesh, through much wantonness, those that were clean escaped from them who live in error. {19} While they promise them liberty, they themselves are the servants of corruption: for of whom a man is overcome, of the same is he brought in bondage. {20} For if after they have escaped the pollutions of the world through the knowledge of the Lord and Saviour Jesus Christ, they are again entangled therein, and overcome, the latter end is worse with them than the beginning. {21} For it had been better for them not to have known the way of righteousness, than, after they have known it, to turn from the holy commandment delivered unto them. {22} But it is happened unto them according to the true proverb, The dog is turned to his own vomit again; and the sow that was washed to her wallowing in the mire.
So does the writer of Hebrews:
Hebrews 10:26-29  For if we sin wilfully after that we have received the knowledge of the truth, there remaineth no more sacrifice for sins, {27} But a certain fearful looking for of judgment and fiery indignation, which shall devour the adversaries. {28} He that despised Moses' law died without mercy under two or three witnesses: {29} Of how much sorer punishment, suppose ye, shall he be thought worthy, who hath trodden under foot the Son of God, and hath counted the blood of the covenant, wherewith he was sanctified, an unholy thing, and hath done despite unto the Spirit of grace?
Thus, the tear is made worse. The exposure of the wretchedness of the self-righteous man to the Gospel and the holiness by that Man who was ordained to be the Judge of the living and the dead brings him into the most intense judgment. For he now has a greater standard than the law: he now has the standard of the very God who created the law, Jesus Christ.

You see, when we compare ourselves with the law certainly we fall short, thus earning the wrath of God. For the law worketh wrath. But when compared with Him who actually obeyed the law in thought and action the apostate has actually claimed to hold to that grace that saves and then tries to add to Christ. This is precisely what works/free will does. There will be far greater judgment upon the one who tries to combine Christ with works and those who have been exposed to the grace of Christ than those who have never confessed or never heard the Gospel, but were merely under law.

I hope this helps a little.

Ward Fenley