As John Walvoord states...

Daniel 9:4-27
"The Backbone of Prophecy"

1) Daniel 9:24-27- Represents one of the key verses regarding "end times" prophecy

Daniel 9:24-27 holds the key to all prophetic interpretation and as such is the backbone of biblical prophecy.

Ray Pritchard writes that

If you understand what these verses mean, you will have a good framework for understanding all that the Bible says about the future. Miss this, and Revelation will be a mystery to you…. What is presented here in a condensed form is greatly expanded in the New Testament. This passage is the key that unlocks many other biblical prophecies." Pritchard goes on to add that "If you have wondered where certain popular writers get the concept of a future seven-year Tribulation period, you will find the answer in this passage. Jesus refers to it in Mt 24:15 as does Paul in 2Th2:1-4. And the amazing events of Rev 6-19 are simply an expansion of Da 9:27. What is presented here in a condensed form is greatly expanded in the New Testament. This passage is the key that unlocks many other biblical prophecies."

Chuck Swindoll says that "the vision of the seventy weeks revealed in  Daniel 9:24-27 is undoubtedly "the backbone of Biblical prophecy" concerning Israel, Christ, and the Antichrist. It is also true that fewer predictions in Scripture have been interpreted in as many ways as have the seventy weeks of Daniel.

John Walvoord writes that

The interpretation of the revelation given to Daniel concerning the seventy weeks (Daniel 9:24–27) constitutes one of the determining factors in the whole system of prophecy. The attention given to it by all schools of interpretation, and the attacks upon the authenticity of the book itself combine to focus the white light of investigation upon it. The interpretation of this passage inevitably colors all other prophetic views, and a proper understanding of it is the sine qua non of any student of prophecy." (Bolding added; Bibliotheca Sacra, volume 101, page 30, Jan-Mar, 1944)

2) Daniel 9:24-27 - Outlines the future history of Israel

As will be discussed below, Daniel 9:24-27 lays out in summary form a timetable of the events that will impact Israel. There is no reference whatsoever to "the church" in this passage, although some commentators still imagine some reference to "the church."

a) The Jews could have known the time of the Messiah's arrival.

b) The Jews will be able to know the time of the "Anti-Messiah's" ("Anti-christ") arrival (cf Mt 24:15, 2Th 2:1-4).
 

3) Provides clear evidence that the Bible is inspired by God

The accuracy of the prediction of the coming of Messiah, Prince, is indisputable evidence of that the Bible is not a book inspired by man but could only have been inspired by God Who Alone knows the future.

Sir Isaac Newton, who wrote a discourse on the topic, said we could stake the truth of Christianity on that prophecy alone, made five centuries before Christ.

Respected pastor and author Ray Stedman writes that Daniel 9:24-27 is

one of the strongest evidences to prove the divine inspiration of the Bible. Many (believers) are frequently asked why (they) believe the Bible to be the Word of God, and it is helpful to know certain passages which clearly set forth predictive elements that are unmistakable and which do indicate the ability of the Bible to predict events far in the distant future. This could only be by divine power....(Daniel 9:24-27)  pinpoints the exact moment in history when the Jewish Messiah would present Himself to the Jewish people, and it does so over five hundred years before the event took place. It is so plain and detailed that it has always been an acute embarrassment to Jewish commentators.

4) Substantiates the truth that God is completely sovereign
 

The prophecy in Daniel 9:24-27 is so compellingly accurate, that it leaves no doubt that God is sovereign and in full control over time and the affairs of men. This grand truth should encourage the saint and frighten the sinner who is not yet saved to consider the claims. 
 

5) Has spurred many (Jews and Gentiles) to consider the claims of the Messiah

Although many of the stories are anecdotal (see below), the truth in Daniel 9:24-27 has caused many who seek to refute these prophecies find that they are confronted with indisputable evidence of the Messiah.

6) Refutes the attempt by many to question the date of writing of Daniel's prophecies

Liberal scholars, both Gentile and Jew, have tried to late-date Daniel in order to remove the onus of predictive prophecy. They say the book was written after the events occurred but in such a way as to appear that it was written beforehand. Daniel 9:24-27 is an irrefutable witness that the prophecy of the Messiah's coming and being cut off is true. Since, no one "late-dates" Daniel to the time of Christ, Daniel 9:24-27 is one clear case of predictive prophecy, which establishes the credibility of everything else. This observation also explains why the critics try so hard to debunk this passage.
 

Henry Morris adds that Daniel's

prophecy was given...well over half a millennium before its fulfillment. The probability that Daniel could guess the date of the manifestation and crucifixion of the Messiah is essentially zero. Only supernatural inspiration can account for fulfilled prophecies like this. In fact, these events were fulfilled almost two centuries even after the date assigned to Daniel by scholars who deny that such prophecies can valid!" (The Defender's Study Bible - an excellent resource from a conservative, literal viewpoint by one of the world's leading scholars on creationism)

7) Stimulates a heightened expectation of the imminent return of the Messiah

This statement applies to Daniel in general also, for no book in the Bible says more about the so called "end times" than Daniel. Many orthodox and conservative Jews believe the time is ripe for the coming of Messiah. They see Israel's return to her homeland after more than 1,900 years of national dispersion as having great prophetic significance. They believe the May, 1948 rebirth of Israel and waves of immigration (which is the meaning of the Hebrew word aliyah) from all over the world are converging with many other factors to set the stage for the predicted coming of a national Deliverer. They see the coming of this Messiah as being good not only for Israel but for the whole earth. According to the prophet Isaiah, He will cause the nations to "beat their swords into plowshares, and their spears into pruning hooks; nation shall not lift up sword against nation, neither shall they learn war anymore" (Isa. 2:4).

To quote from an email received February 4, 2004 from "The Temple Mount and Land of Israel Faithful Movement" (an Orthodox Jewish group based in Jerusalem)

"The Hand of G_d appears again and again in Jerusalem and the Temple Mount...to purify the Temple Mount and immediately rebuild the house of G_d as the climax of the exciting redemptional times in which we are now living in Israel which will open the Eastern Gate for the coming of Mashiach ben David", this latter name of course referring to the expected Messiah. Interestingly, both Jews and Christians share the belief that a period of turmoil and distress will precede the coming of Messiah. The Jewish document called "Talmudic Sages" draws a dark picture of this time. Accordingly, one of these Jewish sages wrote, "Let him [Messiah] come, but let me not see him" (Sanh. 98b).

Why interpret Daniel 9:24-27 literally? see Prophecy Primer

One of the most respected names in the study of Bible prophecy, Dr. John Walvoord, writes some sage remarks regarding the interpretative difficulties of Daniel 9:24-27:

In the concluding four verses of Daniel 9, one of the most important prophecies of the Old Testament is contained...Although many divergent interpretations have been advanced in explanation of this prophecy, they may first be divided into two major divisions, namely, the Christological and the non‑Christological views. The non‑Christological approach may be subdivided into the liberal critical view and the conservative amillennial view.

The Christological camp interprets the first sixty-nine weeks of Daniel as culminating in Christ while the non‑Christological  camp finds fulfillment of Daniel’s prophecy in events before or after Christ.

The non-Christological group attempts to find fulfillment of the Daniel's 70 Weeks in the events leading up to the persecution of Antiochus Epiphanes (see Daniel notes and additional discussion). In 168 B.C., a pagan altar was constructed on top of the great altar of burnt sacrifices, and a pagan sacrifice was offered under the reign of Antiochus Epiphanes. This act precipitated the Maccabean revolt which Antiochus attempted unsuccessfully to put down with great cruelty (167-164 B.C.).

Recall that Daniel was written in two languages, Hebrew and Aramaic. From Daniel 2:4b to Da 7:28, 8:1 the language is Aramaic for the focus is on the Gentile world powers that would interact with Israel, and from Daniel 8:1 onward the focus of the book turns from the future of the Gentile world powers to the future of Israel.

Another interesting observation is that in Daniel 9 Yahweh or Jehovah is used seven times but no where else in the entire book!  Why would the Spirit inspire the usage in this chapter? Jehovah is God's covenant name and this chapter preeminently emphasizes that He will keep His promise to bring the Jews back to their land, the land He promised in covenant to Abraham, Isaac and Jacob.

It was C H Spurgeon who said

At the time the prophecy recorded in Daniel 9 was given, the Babylonian Empire had fallen to the Medo-Persian Empire. Cyrus (also referred to as Darius) was in power. Although the Jewish exiles were now the captives of the Medo-Persians, Daniel retained his position as prime minister because of his integrity. Daniel received his revelation in the year 538 BC, about 67 years after he had been taken captive.

Seventy weeks (Leviticus 25:8; Numbers 14:34; Ezekiel 4:6)

Literally 70 sevens or 70 units of seven. (Click discussion of why the number 70 and its  relationship to Sabbath rests)

The NIV (see above) less confusing than the KJV and NAS (both of which translate "seven" with the word "week")...

Seventy 'sevens' are decreed

The Hebrew word for seven (shabuwa', sabua' or shabua') is simply a "unit of seven" and could refer to seven of anything. Our English equivalent is "heptad" which means "a group of seven".

The Theological Wordbook of the OT adds that shabua'

occurs 20 times in the OT, always indicating a period of seven. Indeed, the word obviously comes to us from sheba' and could literally be translated always as "seven-period."

Three times in the OT, shabua' is modified by the Hebrew word for days, with the "seven days" referring to a literal week (Ezek 45:21, Da 10:2-3), 6 times in Daniel 9:24-27 it is used as a unit of seven without an added unit of time and 11 times it is used to mean a literal week of seven days (Ge 29:27-28, Lev 12:5) with 8 of 11 uses referring to the Jewish Feast of Weeks or Pentecost (Ex 34:22, Nu 28:26, Dt 16:9 [x2], 16:10, Dt 16:16, 2Chr 8:13, Jer 5:24). Note for example Leviticus 12:5 which describes the length of time a mother shall remain unclean declaring

she shall be unclean for two weeks... (literally "two sevens" or "two units of seven")

Observe that the context most naturally leads to the interpretation as "two units of seven" days. The Hebrew omits the word for "day", because the meaning is clear from the context. By comparison the Hebrew Daniel 9:24-27 omits the unit of time, because in context the time is most naturally understood as "years". 

Assuming a literal interpretation, seventy weeks or units of seven (seventy heptads, units of measure) can be conveniently divided as follows...

Daniel 9:24 - a comprehensive picture of the entire prophecy

Daniel 9:25 - the first 69 sevens (483 years)

Daniel 9:26 - the events between the 69th and 70th sevens

Daniel 9:27 - conclusion punctuated by the 70th seven of 7 years.

Remember one of our simple but foundational "rules" in interpreting prophecy is that if the plain sense makes good sense, then don't try to make some other sense out of it or it will result in nonsense. To say that the events described in Daniel 9:24-27 occurred in 490 days, 490 weeks or 490 months makes no sense ("nonsense") from the context! Even older commentaries see this as only making sense if it is interpreted as years.

For example Gill writes that 

this space of "seventy" weeks is not to be understood of weeks of days; which is too short a time for the fulfillment of so many events as are mentioned; nor were they fulfilled within such a space of time; but of weeks of years, and make up four hundred and ninety years.

It is often said that in interpretation of Scripture, "context is king" and the verses that follow (Da 9:25-27) provide the major "clue" as the most appropriate unit of time one should use to modify the "seventy units of seven". The rationale for interpreting the unit as years is discussed in more detail elsewhere (click here).

In summary, the context most logically leads one to conclude that Daniel is referring to "seventy sevens" of "years" for a total of 490 years (70 x "7" years = 490 years).

Click for more detailed discussion of why years is the most appropriate unit of time regarding the 70 x 7's.

Have been decreed

determined (KJV)
settled (Berkley)
marked out (New English Bible)
commanded (TLB)
God has set (GNB)
weeks have been fixed (BBE)
assigned (GWT)
God has ordered (NCV)

The Hebrew verb (chathak/hatak) for decreed is in the perfect mood which expresses a completed action. "God said it, so that settles it" is the idea! This Hebrew root word basically means to "cut or divide", "to cut off" and hence to degree or determine.

The picture conveyed by chathak/hatak is of Jehovah, the covenant keeping God (In Daniel Jehovah is found only in Daniel 9 - seven times - read especially Da 9:4) and underscores the important truth that God is sovereign, in complete control of the history of His people Israel and that He has marked out, ordained or predetermined the events that will impact them! Stated another way, it is as if God has "cut off" a segment of time and assigned it for the deliverance and restoration of His people, Israel, and His holy city, Jerusalem with the implication that His plan will be completed in regard to each of the 6 areas in the following discussion.

The Hebrew verb is translated in the Greek Septuagint with a Greek verb (suntemno) that means to cut short, to bring to an end or to accomplish speedily.

Gill also observes that the Hebrew verb chosen here is especially apropos for

the word...to cut aptly expresses the division, or section of these weeks into distinct periods, as seven, sixty two, and one.

For your people and your holy city

The angel Gabriel is speaking to Daniel, a Jew, so his people most naturally and logically refers to the Jews and similarly his holy city is clearly a reference to Jerusalem. Unlike the prophecies in Daniel 2, 7, and 8, which primarily relate to the Gentiles, Daniel 9:24-27 is God's specific program for the people of Israel and for Jerusalem. It is therefore surprising that some scholars who are otherwise generally "conservative" (e.g., Young, Keil, Leupold) interpret "your people" symbolically as a reference to the church, and "your holy city" as a reference to heavenly Jerusalem! As stated earlier, if the plain sense makes good sense, don't try to make some other sense or it's potentially nonsense! There is no mention of the church in this passage. By the time these 490 years run their course, God will have accomplished all 6 predictions, all of which will be realized by Israel at the Second Coming of Messiah when

"all Israel will be saved; just as it is written, "THE DELIVERER (the Messiah) WILL COME FROM ZION, HE WILL REMOVE UNGODLINESS FROM JACOB. AND THIS IS MY COVENANT WITH THEM, WHEN I TAKE AWAY THEIR SINS." (Ro 11:26-27)

At that time the "elect" of Israel will recognize her Messiah, will repents and will turn to Him as her Deliverer, Savior and King and will be restored to the land and blessed, this restoration being ultimately an answer to Daniel’s prayer. Although these six accomplishments speak primarily to Israel, clearly all of humanity will be radically impacted at their consummation, some to their eternal praise and some to their eternal punishment.

Walvoord observes that...

Even in ruins, Jerusalem remains the city set apart in the heart of God (cf. Da 9:20) and Daniel shared this love for the city which is central in God's program for His kingdom both in the past and the future. Unlike the prophecies of Daniel 2, 7, and 8, which primarily related to the Gentiles, this chapter is specifically God's program for the people of Israel, as Daniel would obviously interpret it. To make this equivalent to the church composed of both Jews and Gentiles is to read into the passage something foreign to the whole thinking of Daniel. The church as such has no relation to the city nor to the promises given specifically to Israel relating to their restoration and repossession of the land. (Walvoord, John F: Daniel: The Key To Prophetic Revelation. Moody, 1971)

to finish the transgression: (Matthew 1:21; 1 John 3:8)

"to let wrongdoing be complete" (BBE). 

Literally "to restrain firmly the transgression "

For completeness, it should be noted that there are two Hebrew verbs which are used to translate the phrase finish (click explanation).

Moses' illustrates the meaning of kala' describing the ending of the flood when

the fountains of the deep and the floodgates of the sky were closed, and the rain from the sky was restrained (kala') (Ge 8:2).

Israel's rebellion will be restrained at the Second Coming of the Messiah when a remnant  will turn to Him in faith and the nation’s transgression and sins will be forgiven. Zechariah records God's promise that when the Messiah returns after the decreed 490 years

it will come about in all the land...that two parts in it will be cut off and perish, but the third will be left in it (the "elect" and believing remnant). And I will bring the third part through the fire, refine them as silver is refined, and test them as gold is tested. They will call on My name, and I will answer them; I will say, 'They are My people,' and they will say, 'The LORD is my God.' (Zech 13:8-9)

Transgression (06588) (pesha') means to rebel, revolt or to rise up in clear defiance to authority by  violation of a law, command, or duty. The fundamental idea is a breach of relationship (civil or religious) between two parties. Pesha' speaks of willful sins. And so the first item in God's program is to bring rebellion against Him to an end.

Vine says that pesha'

basically...signifies willful deviation from, and therefore rebellion against, the path of godly living.

Transgression in this verse speaks of a definite rebellion against authority, and the grammatical construction suggests that a specific transgression was intended. This seems to be a reference to the rebellion by Israel specifically against God and His Word.

Showers adds that

this rebellion was the root sin which prompted all of Israel’s other sins. Gabriel was saying that Israel would not stop its rebellion against God’s rule until these 490 years would run their course. In agreement with this, other Scriptures indicate that Israel will not repent, turn to God and be saved until the second coming of Christ at the end of these 490 years (Zech 12:10–13:1; Ro 11:25–27). (The Most High God: Commentary on the Book of Daniel. Bellmawr, NJ: Friends of Israel Gospel Ministry, Inc)

John Walvoord adds that

The most obvious meaning is that Israel's course of apostasy and sin and wandering over the face of the earth will be brought to completion within the seventy sevens. The restoration of Israel which Daniel sought in his prayer would ultimately have its fulfillment in this concept.

In regard to the phrase finish the transgression in Daniel 9:24, the New American Commentary (Daniel: Broadman & Holman Publishers) has this note 

Most authorities (eg KJV, NASB, NIV), taking the qere reading, have understood the Hebrew verb in this first phrase as kālâ, “be complete, at an end, finished, accomplished, spent.” Others (e.g., kethiv, Wood, Young) have taken the word to be kālā, “shut up, restrain, withhold.” If the latter is correct, the idea could be that transgression is not completely stopped but lessened. Yet it could also mean that transgression is restrained completely, at least for a time. Thus the meaning would be very similar to that of kālâ. (Comment: This is a somewhat technical note on Kethiv versus Qere {explained below} in Daniel 9:24. Keep in mind that the Hebrew Bible, the scribes did not alter any text they felt had been copied incorrectly. In the Masoretic Text they noted in the margin what they thought the written text should be and this was designated a Kethiv (or Kethib or Ketib) which literally means "what is written"  and the marginal note is called the Qere (Kere) an anglicized Aramaic word  which means "what is read". Until the time of the Masoretes, the Hebrew Bible was written only with consonants. The Masoretes (name for the scholars whose work it was to maintain the tradition which governed the production of copies of the biblical text, referred to as the Masoretic Text) thought that the vowels would clarify the Scriptures and therefore began to copy them with the vowels. When they came across a word they thought was unclear by its normal vowels, they would put the word in the margin with other vowels, changing the meaning or intent. The word that was written in the text was called the Kethiv and what was to be read was called the Qere which represented the variant marginal reading. There are about 1300 instances of Kethiv-Qere in the Masoretic Text. The note would lead a person reading the text to pronounce the Qere rather than the Kethiv. Qere readings were intended either to correct the Kethiv or to preserve variant manuscript traditions. Now are you totally confused?)