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Hebrews Chapter 8 contains the deepest discussion in all of the NT about the new covenant, and the longest OT quote (from Jeremiah 31:31-34). And this is also where the author of Hebrews makes a pivotal turn in the argument he is developing. One of the reasons Hebrew 8 is so significant is because it’s the only place in the entire New Testament where we find the language of a “first” and “second” covenant, and an old and a new covenant. 

Links mention in this episode
What Makes the New Covenant New? (Article)
What's "New" About the New Covenant? (Video)

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Chapters
00:00 Introduction & Re-cap
04:20 The Text of Hebrews 8:1-13
07:11 Hebrews 8:1-6: High Priest of the True Tent
21:50 Hebrews 8:7-12 The New Has Come
35:30 5 Reasons the New Covenant is New
48:28 God's New Covenant People
52:28 Hebrews 8:13 The Old Has Passed
57:41 The Word "Covenant"