The follow excerpt comes from "Kinship by Covenant: A Canonical Approach to the Fulfillment of God's Saving Promises" by Scott W. Hahn:
Beginning at pg. 307:
"Hebrews 9:15-22 and the Meaning of Diatheke...unfortunately the passage has remained obscure and highly debated in the history of scholarship. The issues are quite complex, requiring analysis of these verses in much greater detail than that required for the tex of Hebrews to this point.
The dispute in Hebrews 9:15-22 is whether to take the word [diatheke] in vv. 16-17 according to its secular Hellenistic meaning 'testament,' or its Septuagintal meaning 'covenant' (berit). Most modern translation and commentators take [diatheke] in the sense of 'will' or 'testament' in vv. 16-17, and as 'covenant' in vv. 15 and 18. For example, the RSV reads:
'(9:15) Therefore he is the mediator of a new covenant (diatheke), so that those who are called may receive the promised eternal inheritance, since a death has occurred which redeems them from the transgressions under the first covenant (diatheke). (16) For where a will (diatheke) is involved, the death of the one who made it must be established. (17) For a will (diatheke) takes effect only at death, since it is not in force as long as the one who made it is alive. (18) Hence even the first covenant (diatheke) was not ratified without blood.'
It is not difficult to see why this approach enjoys majority support. In v. 15, the context seems to demand the sense of 'covenant,' since only covenants have mediators (mesites) and reference is made to the first diatheke, which the author clearly regards as a covenant. However, in v. 16, the requirement for the 'death of the one who made it' would seem to suggest the translation 'will' for diatheke, since covenants did not seem to require the death of their makers. Likewise, in v. 17, the statement that a diatheke takes effect only at death and is not in force while the maker is alive seems to apply only to a will. However, in v. 18, the topic returns again to 'the first diatheke,' that is, the Sinai event, which can scarcely by anything but a covenant.
While the basic case for the diatheke as 'will' or 'testament' in Hebrews 9:16-17 can be seen readily, the reading labors under a number of difficulties...We may summarize these difficulties as follows: First, the use of the term diatheke to mean 'testament' is not in keeping with the author's usual practice. Second, the actual diction and grammar of vv. 16-17 do not describe any known form of first-century testamentary practice. Third, the concept of a 'testament' is incongruous within the author's larger theological matrix. Fourth, the equivocation in meaning of the key word diatheke renders the author's argument logically invalid.
[Difficulty 1: Diatheke in Hebrews]
It is all but incontestable that aside from 9:16-17 the author of Hebrews uses diatheke only in its Septuagintal sense of 'covenant.'....
[Difficulty 2: Diction, Grammar, and First-Century Testamentary Law]
....Another grammatical strain occurs at v. 17a: diatheke gar epi nekrois bebaia, which the NRSV renders: 'A will takes effect only at death.' Literally, however, the phrase reads: 'For a diatheke is confirmed upon dead [bodies].' There is no justification for taking the phrase epi nekrois as 'at death'....The phrase is awkward, especially the use of the plural (nekroi, 'dead [bodies]'), if indeed the author was intending to speak of the death of the testator.'
[Difficulty 3: Incongruity Within the Author's Theological Framework. Example 1: Covenant and Inheritance in Hebrews]
....the Greco-Roman concept of 'testament' is in strong tension with the way inheritance is consistently presented throughout Hebrews, and runs counter to the strategic deployment of the term 'firstborn' in 1:6 and 12:23.
[Difficulty 3 Continued: Example 2: Covenant and Cultus in Hebrews]
The concept of the Hellenistic testament is also at odds with the author's deep concern for cult and liturgy. In Greco-Roman society, a 'testament' was a purely secular and legal instrument. The author of Hebrews, however, treats 'covenant' not only in legal...but also cultic and liturgical terms. Nowhere is this more true than in Hebrews 8-9....In contrast to this, a secular 'testament' involves neither cult nor liturgy, mediator nor priesthood, sacrifice nor sanctuary, cultic law nor transgression thereof...
[Difficulty 4: The Logic of Hebrews 9:11-22]
The logical flow of the syntax of 9:11-22 strongly militates against taking diatheke in vv. 16-17 in a sense different from that which it bears in the rest of the passage. Verse 15 opens with the phrase kai dia touto ('Therefore...'), signaling 'a strong inferential/causal relationship between vv. 15-22 and 11-14.' It is because Christ has entered into the heavenly Holy Place by his own blood (vv. 11-14) that he has become the mediator of a new covenant (diatheke, v. 15). Thus, the meaning of diatheke in v. 15 is qualified by the covenantal concepts present in vv. 11-14. The second clause of v. 15, introduced by the word hopos, is a final clause indicating the purpose or result of Christ's mediatorship of the New Covenant, namely, that the 'elect' may obtain the eternal inheritance. Within this final clause there is a gentive absolute construction: thanatou genomenou...parabaseon ('a death having taken place'), explaining the circumstances attendant on the acquisition of this inheritance: a death has taken place. The hopou gar ('For since...') of v. 16 introduces a parenthetical explanation of this genitive absolute phrase, explicating why it was that a death had to take place. Verse 17 provides further explication (gar, 'for') of v. 16. The first word of v. 18, hothen ('Hence,') implies that the following unit (vv. 18-22) follow logically from the statements of the previous one, vv. 16-17. Therefore, vv. 18-22 are syntactically linked to vv. 16-17, which are in turn linked (as an explanation) to a clause of v. 15, 'which itself is the climax of vv. 11-14.' The subunits vv. 11-14, v. 15, vv. 16-17, and vv. 18-22 flow (at least syntactically) from one to another as stages in a logically progressing argument. It would be, a priori, unlikely for the author of Hebrews, in the midst of this tightly knit argument, to use diatheke in vv. 16-17 in a sense entirely different from that used in the rest of the passage; and unlikely or not, it would seriously damage the logical coherence of the whole argument. If diatheke means 'testament' in vv. 16-17, one must endorse Kilpatrick's assessment that 'basically the idea of testament fits into the passage very clumsily,' and Behm's that '[the author] jumps from the religious to the current legal sense of diatheke...involving himself in contradictions which show that there is no real parallel.'
...
Exegesis of Hebrews 9:15-18
...It is not covenants in general, but this broken, lethal Sinai covenant that forms the context within which the statements of vv. 16-17 should be understood.
Assuming a context in which 'transgressions have taken place' from v. 15, the author's meaning can be clarified as follows:
[v. 16]
Since there is a [broken] covenant,
it is necessary for the death of the
covenant-maker to be borne,
[v.17]
For a [broken] covenant is enforced
upon dead bodies;
for it is certainly not in force while the
[offending] covenant-maker lives.
[v.18]
Hence, not even the first [covenant]
was ratified without blood.
....[since the Sinaitic covenant was] ratified by a bloody sacrifice (vv. 18-22, cf. Exod 24:5-8), which entails a curse of death for unfaithfulness--'the death of the covenant-maker must be borne.' The author does not says: 'The covenant-maker must die,' but uses the circumlocution: 'The death of the covenant-maker must be borne,' in order to leave open the possibility that a suitable representative may bear the punishment of death on behalf of the covenant-maker, as Jesus does for Israel and all mankind (Adam).
The concept of someone 'bearing' (phero) the death of the covenant-maker in 9:16, like the 'bearing (anaphero) the sins of many' in 9:28, may be shaped by the use of phero in Isaiah 53 LXX, where (ana) phero is consistently used in the sense 'bear something for another.'....the clear reference to Isaiah 53:12 in Hebrews 9:28 makes it plausible that the use of phero in the sense of 'bear on another's behalf' in Isaiah 53:3-4 lies behind the use of phero in Hebrews 9:16.
The sense of the following phrase (v. 17a), 'a covenant is confirmed upon dead [bodies],' (diatheke gar epi nekrois bebaia) is that, after a covenant has been broken (i.e., the situation under the first covenant), the only means of upholding the covenant is to actualize the covenant curses, which ultimately--if not immediately--result in the death of the covenant-maker-turned-covenant-breaker.
The principle underlying the bold statement of v. 17b, 'since it certainly is not in force while the covenant-maker lives' (epei mepote ischyei hote ze ho diathemenos), is this: for the covenant-maker(s) to remain alive after breaking the covenant indicates that the covenant has no teeth, no binding force (mepote ischyei)....
The following verses (9:18-22) explicitly concern the first Sinaitic covenant. The sense of v. 18, ["Hence, neither was the first covenant inaugurated without blood,'] the emphasis being on the fact that, at its very inception, the first covenant already symbolized and predicted the necessity of the death of the covenant-maker in the case of transgressions. Therefore the reader should have no doubt that the Sinaitic covenant was one that entailed the curse of death.
The net effect may be summarized in the following way: With the breaking of the ('first') covenant, Israel's death becomes legally necessary because of the curses signified by the sacrifice. Once Israel breaks the covenant, it is divinely renewed--but only symbolically--through Moses and the apparatus of the Levitical priesthood....the divine court was temporarily adjourned so that the execution of the covenant curses could be delayed and deferred until someone could bear the curses--vicariously and redemptively--and so release the covenant blessings.
Christ thus fulfills the Old Covenant by bearing the curse of death as a faithful son of God an royal high priest, thereby performing the vocation that Israel first accepted (Exod 19-24) and then spurned with the golden calf (Exod 32)...The death of Christ...simultaneously [expiates the curse of death of the Old Covenant and provides the inaugural sacrifice that ratifies the New Covenant]."
Hebrews 9:15 and the Old and New Covenants
Hebrews 9:15 succinctly states the author's foundational understanding of how Christ inaugurates a new covenant:
[15a]
'Therefore He is the mediator of a new covenant,
[15b]
so that those who are called may receive the promised eternal inheritance,
[15c]
Since a death has occurred which redeems them from the transgressions under the first covenant.'"