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Many people think there is a conflict between the “letter of the Law” and the “Spirit”, based on certain passages in the New Testament. Most notably,

“You were made dead with regard to the Torah through the Messiah's body, so that you could come to belong to another—to the One who was raised from the dead, in order that we might bear fruit for YHWH. For whenever we [operate] in the flesh, the sinful passions in our members are aided by the Torah in bearing fruit for death. But now we have been released from the Torah by dying in relation to that which firmly kept us in its possession, so we can serve in the newness of spirit, and not in the old [manner]—that of letter.” (Roman 7:4-6)

They deduce that the distinction that is being made is between following the Torah (the “Old Testament” way) and following the Holy Spirit’s leading (the “New Testament” way).

But is the Holy Spirit (literally, the spirit of being holy) going to lead us contrary to YHWH’s commands, which are the foundation of all of His revelation about what holiness means? (Lev. 11:45-47) The very context precludes that view, for it goes on to say, “What should we say, then? ‘The Torah is in error’? Never!” (Romans 7:7) “Thus the Torah is indeed holy, and the commandment, holy and just and right.” (7:12)

The problem that made the Torah and the flesh allies in an unholy way, he says, is that “I did not understand that there was such a thing as covetousness, except that the Torah said, ‘You shall not covet.’ In other words, sin, taking occasion through the commandment, was empowered to produce in me every sort of coveting… The commandment that was designed [to bring] life turned out in my case to [be bringing] death, because sin, seizing the occasion through the commandment, deceived me… For we know that the Torah is spiritual; however, I am carnal, having been sold into [slavery to] sin.” (7:7-14)

His solution? Something more fundamental than even the Torah is needed to really change our natures, and that was accomplished when the Second Adam passed the test the first Adam did not, and was able to pass on to us the image of Elohim that he had regained for mankind. No conflict with the Torah itself, but a much more comprehensive provision that allows us to successfully cooperate with the Torah.

But our antagonists point out another passage: “Our sufficiency comes from Elohim, who has qualified us [to be] ministers of a fresh covenant, not of letter, but of spirit, because the letter puts to death, while the spirit brings to life.” (2 Corinthians 3:5-6)  

See? The Torah is about death, but the spirit is about life! They are the opposite of each other! Right?

Well, no; Moshe defines obedience to the Torah as choosing life rather than death. (Deut. 30:19) It’s disobedience to the Torah that brings death; the letter just delivers the message. But the real question this begs is, what spirit are we talking about here? The term “spirit” can mean an awful lot of things, even within different parts of Scripture. (See “What is the Holy Spirit?” for more about this.)

  
If the letter has to do with the Torah here, it would stand to reason that the spirit being spoken of in these passages is also the spirit of the Torah, rather than the Holy Spirit as such.

  
So what would that mean?  Dictionary.com lists two angles from which this sense of “spirit” should be understood: “An attitude or principle that inspires, animates, or pervades thought, feeling, or action” (as in “the spirit of reform”) and “the general meaning or intent of a statement, document, etc.” (as in “the spirit of the law”). 
In other words, it is that which motivates the letter—the reason behind the commandments, for unless we think YHWH just wants us to jump through random hoops for no reason but to see whether we will obey, His commandments are not given in a vacuum. They all fit together, and they have a purpose.

Many commands are really samples of such an underlying principle on which the specifics are based.

In Matthew 5:27-28, Yeshua says, "You have heard that the ancients were told, 'Do not commit adultery'. However, I tell you, everybody who looks at a woman for the purpose of lusting after her has already committed adultery with her in his heart.”

Michael Rood writes, “This is a perfect example of the spirit of the Torah. Messiah interpreted the heart of this instruction to mean that [YHWH] wants us to not only refrain from the act, but we are to control our mind so that our imagination does not even consider the possibility of fleshly fulfillment. We should be able to trust each other around our wives, sisters, and daughters. This is the spirit of the Torah, which in this instance is more restrictive than the letter of the Torah.”

If you live by the spirit, then, you will not be in danger of breaking the actual command, because you will already be armed with the mindset that the command is based on, and you will not even get close to doing what is forbidden. The spirit, then, is enough of a “fence around the Torah”, so that there is no need to add human regulations which always prove to have a flaw where you need it least, for if you add to the Torah, you by definition cannot keep the Torah (Deut. 4:2), because to add on this side you will have to take something away from another commandment, and they are no longer in the perfect balance in which YHWH set them.

Yeshua goes on to do more such radical investigations of the commands (for “radical” means “getting to the root”):

“"You've heard that the ancients were told, 'Do not commit murder!' and 'Whoever murders will be liable to the court.' But I tell you, everyone who is angry with his brother without a valid reason also deserves to go before the court. And whoever says to his brother, 'You good-for-nothing!' will be liable to the high court...” (Mat. 5:21-22)

Get it? Baseless anger and despising of another human being made in Elohim’s image are roots of murder, for murder does not just “happen” without something leading up to it. It starts with hate (Deut. 19:11), so nip the hate in the bud, and you will never get to the point of murder.

  
That is what the spirit of the Torah means. And that is how “your righteousness goes beyond that of the scribes and P'rushim” (Mat. 5:20), for many of them, though super-religious, were full of hate and despised their neighbors who were not so observant as they. (Luke 18:11)

Yeshua said the whole Torah “hangs” on two of its commands—i.e., which show more obviously what the rest are all about: “Love YHWH with all your heart, your appetites, and your intensity” and “Love your neighbor as yourself”. (Mat. 22:40) 

 Paul reiterates this:

“Leave no debt to anyone outstanding, except to watch out for each other's welfare, because the one who looks out for his neighbor's best interests has fulfilled YHWH's intent in giving the Torah—because ‘Do not commit adultery’, ‘Do not commit murder’, ‘Do not commit a theft’, ‘Do not bear false witness’, ‘Do not covet’, and whatever other commandment there may be, it is summarized in this consideration: ‘You shall love your neighbor the same way that you love yourself.’ Love does no wrong to one’s neighbor; therefore love is the fulfillment of the Torah.” (Romans 13:10)

Even if the way you love your neighbor is not directly mentioned in one of the commandments. That is what “not according to the letter” means.

So the contrast being drawn between “letter and spirit” is not between the Torah and the Holy Spirit (which is indeed essential if we are to sense and understand the spirit of the Torah), but between the precise adherence to only what the text says directly and the attitude which the particular commands exemplify, which is often more fluid, but still made of the same substance.

They are not contrary to each other; you are just not bound to the particular example/instance employed in framing the command, once you understand the underlying principle that has much wider application.

  
Not that we would go directly against any of the commandments; we just might use a different version of it in the present situation, fleshing it out in a way more particular to what we are facing at the moment rather than in the way that was needed in the wilderness of Sinai or in ancient Israel.

The letter is the mandatory starting point, so that we will not interpret love as a nebulous “spirit” of anything we want it to be. Nowadays, “hate speech” is redefined as anything that critiques or disagrees with another’s viewpoint, so, by that token, “loving” would have to mean letting someone live whatever lifestyle he wants to live and affirming him in it—not “caring enough to confront”, as one author described the real meaning of love (wanting and doing what is best for another, even if the truth is hard to swallow). So the commands show the parameters of how love can and cannot be defined. Each command sets limits on how we interpret every other command.

But the letter is still just the launching point into depths that we cannot see on the surface, when taken only at face value. Yes, there is more to the Torah than just the literal sense (“the letter”). Even traditional Judaism, which many associate only with strict adherence to the letter, says there are at least three other levels on which every Scripture can be read. We won’t go into them all now, but suffice it to say that interpreting a passage in a prophetic sense does not cancel or discount the simplest, most obvious immediate meaning the original hearers understood, nor does taking it literally mean there are not also figurative ways it can be taken--or applied. The Hebraic mindset is that if it can be understood more than one way, it probably should be, for there is something profitable to learn from each angle we can see it from.

 
The letter is not always as specific as many have wanted it to be, hence the Talmud (and its “oral Torah” theory), which is designed to “fill in the gaps” so we know exactly how to carry out the command. But even there, numerous viewpoints are brought forward, hinting that maybe YHWH deliberately left some commands vague—so that they could be carried out equally validly in many different contexts, which do not always permit doing things the more rigid way the human commentaries would dictate. We can’t improve on YHWH’s way of doing things. But He can enhance His own workmanship:

“Since the Torah was… weakened due to [our] natural condition, YHWH (by sending His own Son in the likeness of sinful flesh and [specifically] to deal with sin) decisively exposed sin in the flesh for what it really is, in order that the righteous requirement of the Torah may be fulfilled in [those of] us who are not ordering our lives according to flesh but according to spirit.” (Romans 8:3-4) The Greek term for “decisively exposed” carries the connotation of demonstrating the inferiority of one thing by the presence of something that does the job better. By showing us what a sinless man could be, Yeshua shone the spotlight on what we could have been but were not, thus highlighting the fact that in our condition, measuring ourselves against one another would not mean we met the actual standard, but that if we let him lead the way at each crossroads, we could still fulfill the intent of the Torah though we did not carry out every single aspect of it perfectly.  

YHWH may forgive our shortfall in some aspects of the letter if the spirit is right. During a time of great spiritual revival, we read that “a large number of the people—many from Ephrayim, M’nasheh, Issachar, and Z’vulun—had not purified themselves, yet they ate the Passover, contrary to the way it was written. But Hizqiyahu interceded for them, saying, ‘May YHWH, who is good, provide atonement for everyone who sets his heart on seeking Elohim—YHWH, the Elohim of his fathers—even if he is not cleansed according to the purification rules of the sanctuary.’” (2 Chronicles 30:18-19)

But we should not presume on this; notice that atonement had to be made in order to allow for this. YHWH has provided atonement through Yeshua, but we need to remember how high that price of our being granted this indulgence really was. Remember Paul’s word to the Athenians: “In the past YHWH overlooked the times of ignorance, but now He is calling everyone everywhere to repent.” (Acts 17:30)

But the point seems to be that attitude trumps perfection in every detail, especially if we are still earning or do not have access to all the facts:

“Won't those who are physically uncircumcised, by keeping the law [nonetheless], call into condemnation [those of] you who transgress the Torah, though you have the letter and are circumcised? For… he is really a Jew who is one inwardly (and the truest circumcision is of the heart, not so much in letter as in spirit)— who is praised not by men, but by YHWH.” (Romans 2:27-29, based on Deuteronomy 10:16)

“Not so much…” I think that rendering captures the intent much better than “Not according to the letter, but according to the spirit”, for “not this but that”, in Hebraic idiom, does not always mean we must choose one thing instead of the other (that is expressed a different way), but really connotes, “This is the more important point”. 

When it’s “this more than that”, we still don’t ignore the letter. Even when Yeshua said, “Woe to you, scribes and P’rushim, hypocrites who tithe mint, rue, and cumin, but have left out those matters within the Torah that are more important—justice, kindness, and faithfulness,” he followed it up with, “Those you ought [indeed] to have done [too], but not neglected these [either]…” Though he critiqued the “hypocrites who clean the outside of the cup or the bowl, but inside they are full of embezzlement and impurity”, he did not say the outside was of no importance; he said to “start by cleaning what is within the cup or the bowl, so that the outside may also be pure.“ (Mat. 23:23-26)

Both are crucial, so hold onto both, but keep the horse before the cart.

The Spirit of the Torah