So you are to know and discern (Da 9:23; Matthew 13:23; 24:15; Mark 13:14; Acts 8:30)

Know and discern - Gabriel begins with an exhortation.

Know (03045) (perceive, understand) (yada') by observing, reflecting upon and becoming "intimately" acquainted with the important truth and timing of events to follow.  The Greek Septuagint translates know with ginosko meaning to "know by experience" speaking of an intimate knowledge that goes beyond the accumulation of facts.

Discern (07919) (have insight or comprehension, be prudent or circumspect, give attention to or ponder) (sakal) is somewhat synonymous with "know" but expresses the idea of knowing the reason for something by looking at it or giving attention to it. 

Sakal implies the process of thinking through a complex arrangement of thoughts (for which Daniel 9:24-27 certainly qualifies!) resulting in a wise dealing and use of good practical common sense with the end result that one is successful.

The TWOT says that sakal...

also involves one in what he considers, or pays attention to.

Discern is translated with the Greek verb suniemi which entails the assembling of individual facts into an organized whole, as collecting the pieces of a puzzle and putting them together. The mind grasps concepts and sees the proper relationship between them.

Commenting on Daniel 9:24-27 Matthew Henry writes that

We have here the answer that was immediately sent to Daniel's prayer, and it is a very memorable one, as it contains the most illustrious prediction of Christ and gospel-grace that is extant in all the Old Testament. If John Baptist was the morning-star, this was the day-break to the Sun of righteousness, the Day-spring from on high.

Reginald Showers of the Friends of Israel Gospel Ministry writes  that Daniel 9:24-27 is

one of the most significant prophecies in all the Old Testament Scriptures" and is also "one of the strongest biblical evidences to the effect that Jesus of Nazareth is the Messiah.  (The Most High God: Commentary on the book of Daniel)

that from the issuing of a decree to restore and rebuild Jerusalem: (Click additional notes) (Ezra 4:24; 6:1-15; 7:1,8,11-26; Nehemiah 2:1, 2, 3, 4, 5, 6, 7,8; 3:1) (2Samuel 15:25; Psalms 71:10)

Jerusalem will be rebuilt with streets and strong defenses (CSB)

Streets will be built in Jerusalem, and a trench will be dug around the city for protection (CEV)

the street shall be built, and the wall (Brenton's Eng of Greek Septuagint)

From the issuing of a decree to restore and rebuild Jerusalem - This is the key to the interpretation of this entire passage and obviously the critical determinant is when does the "countdown" begin in history (the so-called "terminus a quo")

The decree (dabar = literally "word") although made in heaven, would be made manifest on earth which would have been wonderful news to Daniel. The important question is which "decree" marks the commencement of the 490 years?  There are 4 possible "candidate" decrees (listed below):

Of the four "candidate" decrees, the one which most literally fulfills the specific requirements in Da 9:25 is found in Nehemiah in which he records that

it came about in the month Nisan (March-April), in the 20th year of King Artaxerxes..(444/445BC). 3 (Nehemiah) said to the king, "Let the king live forever. Why should my face not be sad when the city, the place of my fathers' tombs, lies desolate and its gates have been consumed by fire (which would make the city defenseless)?" 4 Then the king said to me, "What would you request?" So I prayed to the God of heaven. 5 And I said to the king, "If it please the king, and if your servant has found favor before you, send me to Judah, to the city of my fathers' tombs, that I may rebuild it." ... 8 and a letter to Asaph the keeper of the king's forest, that he may give me timber to make beams for the gates of the fortress which is by the temple, for the wall of the city, and for the house to which I will go." And the king granted them to me because the good hand of my God was on me. (Neh 2:1-8)

The plaza (07339) (rehob) refers to an "open place" which came to mean a public square, city-hub, central part of city where people met and civic activity occurred. Rehob was first used in Genesis 19:2 when the angels told Lot "we shall spend the night in the square".  In summary, rehob, describes the broad spaces, generally just inside the city gates where one see the center of city life. The Greek Septuagint (LXX) translates rehob with plateia and describes a wide or broad street or way.

The moat (02742) (charuts/harus) is used only here in the OT and conveys the basic sense of "to cut or sharpen". In Hebrew charuts/harus means to cut in or dig, and in context refers to a

defensive trench, ditch, i.e., a moat as a defense feature of a rampart (Swanson, J.. Dictionary of Biblical Languages with Semantic Domains : Hebrew -Old Testament,1997).

The idea is that a trench or ditch is dug or "cut out" around a city for the purpose of fortification. This same word in Aramaic refers to a trench and in Akkadian to a city moat. 

The Greek Septuagint (LXX) translates charuts/harus with the Greek word teichos which describes a wall, especially a wall of a city or town which was used to provide strong fortification. Teichos is also used in the rabbinic literature to mean a wall, frequently one designed for defense.

Some argue that the word for moat is not the same Hebrew word used for wall in Nehemiah 2:8, but they miss the point that both have a similar function.

Nehemiah 2:8 ...the wall (Hebrew = chomah, Lxx = teichos) of the city...

Furthermore, note that the Septuagint translates the Hebrew word for wall in Nehemiah 2:8 with the same word used in Daniel 9:25, teichos, the specific word for wall! In Ancient times cities had walls and moats to defend against enemy attack. A "city" without such protection was not really a functional "city".  

In summary, the evidence is extremely convincing that the starting date for the countdown of the 490 years is found in Nehemiah 2.

Prior to Artaxerxes' decree in 444/445BC, the Temple rebuilding had begun but the city itself was still unprotected. Nehemiah was charged by the king to restore the raised city to its former defensible state, which is compatible with the prophetic description in Daniel 9:25.

In regard to the date of Artaxerxes' decree Dr. Hoehner goes through a discussion (too detailed for these notes) and concludes that "Nisan 444 BC (March 5, 444BC) marks the terminus a quo (point of origin) of the seventy weeks of Daniel  9:24–27" rather than the date found in many texts of 445BC. (For detailed discussion see Harold W. Hoehner Chronological Aspects of the Life of Christ - Part 6 - Daniel’s Seventy Weeks and New Testament Chronology - Bibliotheca Sacra 132:525 Jan 1975. Pages 48-65). (Note: only a portion of this article is available at no charge - see Theological Journal Subscription info) (List of 22 journals - 500 yrs of articles searchable by topic or verse! Incredible Online Resource!)

It is interesting that this decree in Nehemiah was also the one favored even as early as the second to third century AD by Africanus, one of the "early church fathers".

Click Thomas Ice's discussion of the beginning of the countdown.

until Messiah the Prince (John 1:41; 4:25) (Da 8:11,25; Isaiah 9:6; 55:4; Micah 5:2; Acts 3:15; 5:31; Revelation 1:5; 19:16)

Messiah the Leader (Young's Literal),
the Anointed One, a Prince (Amplified),
Christ the Prince (English of Greek Septuagint),
the Anointed One, the ruler (NIV),
an anointed prince (NRSV),
an Anointed Prince (NJB),
God's chosen leader (TEV),
the appointed leader (NCV),
one who is anointed and a leader (NAB),
a prince, on whom the holy oil has been put (BBE)

Although the opinions are nearly unanimous among evangelical conservative scholars that this phrase is a clear prophetic reference to the first coming of Christ our Lord, it must be kept in mind (especially if discussing this passage with someone who may not believe in the literal interpretation of Scripture) that there are some who will see the prophecy as fulfilled in the lives of other individuals (click here to see why some Bible versions also do not support the Messianic interpretation).

Until (05704) follows 69 seven's or 483 years. As indicated in the chart below (click countdown), of those that interpret Messiah as reference to Christ there are two major views as to the termination of this time period. One view favors the termination as coinciding with His baptism and others (most modern, conservative, evangelical commentaries) favor this time as coinciding with the triumphal entry of Messiah into Jerusalem. (Click here for discussion by John MacArthur)

John is the only NT writer to use the word Messiah...

He found first his own brother Simon, and said to him, "We have found the Messiah" (which translated means Christ). (John 1:41)

The woman said to Him, "I know that Messiah is coming (He who is called Christ); when that One comes, He will declare all things to us." (John 4:25)

Messiah (04899) (Mashiyach/Mashiach from mashach = basic meaning is to smear something on and conveys the idea of anointing something as act of consecration) is an adjective often used as a noun and is one of the most important words in the OT. An "anointed one" would have sacred oil poured on their head, which set them apart as an individual with a special authority and/or function. And so we see that  patriarchs, priests (Lev 4:3), or kings (Cyrus Isa 45:1) were anointed ones.

In Psalm 2 Mashiyach clearly refers to the Messiah, the Christ...

Psalm 2:2 The kings of the earth take their stand, And the rulers take counsel together Against the LORD and against His Anointed (Hebrew = Mashiyach > "Messiah"; Lxx = Christos = one who has been anointed).

As Pfeiffer says there is no doubt that this time refers to

Some official presentation, such as his baptism and the formal beginning of his ministry, or His triumphal entry. (The Wycliffe Bible Commentary: Old Testament Chicago: Moody Press)

Although I realize that one must be careful being dogmatic, this website does favor the termination of the 69 weeks on the day of the triumphal entry of Jesus into Jerusalem when He was presented to the Jews as their King.

Robert Anderson (The Coming Prince in 1894) and Harold Hoehner (in 1976) have independently calculated that following the decree to rebuild Jerusalem (Neh 2:1-8) until Messiah, the Prince was 177,880 days which by their calculations coincides with the very day Jesus entered Jerusalem (Palm Sunday) riding on a donkey fulfilling Zechariah's prophecy

Rejoice greatly, O daughter of Zion! Shout in triumph, O daughter of Jerusalem! Behold, your king is coming to you; He is just and endowed with salvation, Humble, and mounted on a donkey, Even on a colt, the foal of a donkey. (Zech 9:9)

Although prince (05057) (nagiyd) is not the usual Hebrew word for king (melek), it is notable that the first use in Scripture  is a reference to Saul, God informing His prophet Samuel that

I will send you a man from the land of Benjamin, and you shall anoint him to be prince (nagiyd) over My people Israel; and he shall deliver My people from the hand of the Philistines... (1Sa 9:16)

There are numerous other examples of nagiyd used as a synonym for kings in the OT, so although some argue that the specific Hebrew word for "king" is not used in Daniel, nagiyd conveys the same idea. It follows that it is reasonable to interpret Daniel 9:25 as a reference to Messiah as King of Israel.

The Greek translates prince with the Greek "hegeomai" which speaks of one who leads out and is the same word in Matthew used quoting Micah's prophecy that "out of you (Bethlehem) shall come forth a Ruler (hegeomai), Who will shepherd My people Israel" (Mt 2:6), a reference to the Messiah Who came to lead and rule Israel. 

And so we see that as Jesus rode into Jerusalem on Palm Sunday, the Jewish crowds cried

"BLESSED IS THE KING WHO COMES IN THE NAME OF THE LORD (quoted in part from Ps 118:26 but see note in next paragraph). Peace in heaven and glory in the highest!" 39 And some of the Pharisees in the multitude said to Him, "Teacher, rebuke Your disciples."40 And He answered and said, "I tell you, if these become silent, the stones will cry out!" 41 And when He approached, He saw the city and wept over it, 42 saying, "If you had known in this day (KJV has "in this thy day" but modern manuscripts lack the "thy". Note definite article before "day" which clearly singles this out as not just any day, but a specific day and one the Jews could and should have known if they had studied Daniel 9:24-27), even you, the things which make for peace! But now they have been hidden from your eyes. 43 For the days shall come upon you when your enemies will throw up a bank before you, and surround you, and hem you in on every side, 44 and will level you to the ground and your children within you, and they will not leave in you one stone upon another, because you did not recognize the time of your visitation (the "visitation" of the Messiah in His first advent - they could have calculated His arrival date from Daniel's prophecy but instead they obscured the truth and even refused to read or discuss Daniel 9:24-27 evidencing their rebellious hearts!). (fulfilled in the destruction of Jerusalem and the Temple in 70AD some 40 years later)"  (Lu 19:38-44).

Two observations are significant regarding the Jewish crowd's quotation from Ps 118:26:

(1). The original Psalm (in Hebrew and the Greek) does not have the word king (Hebrew = melek, Greek = basileus) which is used only in Luke's account (but not in Mt 21:9 or Mk 11:9). Mark however does follow the quotation from Ps 118:26 with the "kingly" declaration...

Blessed is the coming kingdom (basileia related to basileus = king) of our father David; Hosanna in the highest! (Mk 11:10)

(2) Jesus even when he was admonished to rebuke the crowd for calling Him King, refused to do so, declaring in fact that

if these become silent, the stones will cry out! (Luke 19:40)

What would they cry out? That the King of the Jews had arrived, just as had been precisely prophesied by Daniel 9:24-25, 173,880 days earlier! Only on this day did our Lord offer Himself publicly and officially as Israel's Messiah and this was the day Anderson and Hoehner calculated had been prophesied by in Daniel 9! It is also noteworthy that all four gospels record the inscription above Jesus' head on the cross as the King of the Jews.

Anderson (see The Coming Prince) adds that

No student of the Gospel narrative can fail to see that the Lord's last visit to Jerusalem was not only in fact, but in the purpose of it, the crisis of His ministry, the goal towards which it had been directed. After the first tokens had been given that the nation would reject His Messianic claims, He had shunned all public recognition of them. But now the twofold testimony of His words and His works had been fully rendered, and His entry into the Holy City was to proclaim His Messiahship and to receive His doom. Again and again His apostles even had been charged that they should not make Him known. But now He accepted the acclamations of "the whole multitude of the disciples," and silenced the remonstrance of the Pharisees with the indignant rebuke, "I tell you if these should hold their peace, the stones would immediately cry out. (Luke 19:39, 40)

C H Spurgeon writes that...

there will be seven weeks and sixty-two weeks

The text does not associate a specific event with the first seven "seven's", therefore we need to be careful not to be dogmatic. The two most frequent events mentioned are (1) the time to completely rebuild Jerusalem or (2) the time at which the Old Testament canon was completed.

Some commentators such as M R DeHaan state that...

It is a matter of history that the rebuilding of the walls of Jerusalem and the Temple and all of the streets, and so forth, took exactly forty-nine years, fulfilling the first division of the seventy weeks of Daniel which was up to the completion of the Temple in the city of Jerusalem. (De Haan, M. R. (1995). Daniel the prophet. Originally published: Grand Rapids, Mich. : Zondervan, 1947. Grand Rapids, MI: Kregel Publications) (Comment: In fact this terminus cannot be historically verified with absolute certainty so we had best avoid dogmatism. In any event the fulfillment pales in comparison to the fulfillments in the following sections!)

Comparison of two translations of the next time phrase And sixty-two weeks (NASB) reveals two modes of translation...

The RSV (rendered the same way in the ESV, Good News Translation, Bible in Basic English, Tanakh, New American Bible, The Message click here) bases the English rendering of this time phrase on the additions of Hebrew scholars known today as the Masoretes. The Masoretes added an accent (called a "atnach") to the original Hebrew manuscripts, the accent in this case being placed between the two time phrases "seven weeks" and "sixty-two weeks".  The RSV translator felt that this Masoretic accent justified placing a period at the end of "seven weeks" and beginning another sentence to which they added the time phrase word "then".

The RSV reads as follows:

Know therefore and understand that from the going forth of the word to restore and build Jerusalem to the coming of an anointed one, a prince, there shall be seven weeks. Then  for sixty-two weeks it shall be built again with squares and moat, but in a troubled time. (The ESV although generally a good and relatively literal translation is not good in this verse and is rendered "Know therefore and understand that from the going out of the word to restore and build Jerusalem to the coming of an anointed one, a prince, there shall be seven weeks. Then for sixty-two weeks it shall be built again with squares and moat, but in a troubled time)

So what difference does this make in one's interpretation? For one thing, many Jewish rabbis will reference this Masoretic "accent" as a major line of evidence to refute the fact that Daniel 9:24-27 is referring to the coming Messiah. If we read the RSV literally, we are indeed forced to interpret Daniel 9:25 as a reference to "an anointed one, a prince" as coming on the scene after "seven weeks" (49 years) from the decree to rebuild Jerusalem. Clearly this view would not allow one to interpret the "anointed one" as a reference to the Messiah. Those who favor the RSV are forced into a non-messianic interpretation of the "anointed one". And thus depending on which commentary you consult, attempt to identify the anointed one as King Cyrus (called anointed in Isa 45:1), Zerubbabel or Joshua the High Priest (priests were anointed). Then they are forced to interpret the second anointed one in Daniel 9:26  as a reference to Onias III (also called Oniah), a Jewish high priest (therefore "anointed") who was displaced and then killed ("cut off") during the reign of Antiochus Epiphanes (circa 171 BC) (see Daniel notes and additional discussion),. The upshot is that the passage has then been emptied of any valid Messianic interpretation! It is not surprising that the liberal, critical school of interpretation follows this line of reasoning and similarly it is not surprising that many in this school even deny that Daniel wrote Daniel! They postulate that Daniel was written some time in between 200-100 BC, after the events had historically taken place.

Arguments against the RSV rendering

(1) The Greek translation of the Hebrew is an older manuscript than the Masoretic additions and does not support the RSV (ESV, NAB, GNB, BBE, Message) but does support the NAS, NIV, KJV, NKJV, etc.  The Greek reads "until Christ the prince there shall be seven weeks, and (the Greek conjunction "kai" = "and" is present in the Greek) sixty-two weeks" (Brenton's English Translation). The Greek reading allows for the interpretation of two time periods as successive periods.

(2) The RSV (and "RSV-like" renderings) force a cumbersome translation which reads as if it will take 62 "sevens" or 434 years to build the temple and moat, which is nonsense!

(3) Regarding the insertion of this accent (atnach) mark by the Masoretes, even Keil and Delitzsch remark that "the atnach does not always separate clauses, but frequently also shows only the point of rest within a clause; besides, it first was adopted by the Masoretes, and only shows the interpretation of these men, without at all furnishing any guarantee for its correctness."

(4) The Hebrew Masoretes added their interpretative marks hundreds of years after the original Hebrew manuscript (and hundreds of years after the Greek translation) leading some to suggest that they may have had a possible anti-Christian bias.

What a difference a single accent mark makes in the interpretation of this important prophecy! Now are you totally confused? I pray not and in fact as you read this my prayer is that of Paul

that the eyes of your heart may be enlightened, so that you may know what is the hope of His calling, what are the riches of the glory of His inheritance in the saints. (Eph 1:18-note)

Please do not let this discussion shake your confidence in the truth that God's Word is fully inspired and inerrant. If you would like to read a more detailed discussion, click this link for Randall Price's analysis and scroll down the page to section subtitled "Question of the Division of the Seven and Sixty-two Weeks".

Pfeiffer comments that...

The reasoning and evidence behind the RSV, (Ed note: I would unfortunately have to add the ESV) which renders this clause quite incomprehensible, is most obscure, though the effect—to make the prophecy focus on Antiochus rather than on Christ—is plain enough. The Berkeley Version is no better. Both seem to destroy the essential reference to Christ in this verse. As a matter of fact, 7 plus 62 equals 69; 69 x 7 = 483. From 444 B.C. to about 30 A.D., the general period of Christ’s ministry is 470 plus years—so close to the specified 483 that without further refinement the correspondence is quite convincing—and as precise in proportion as the 70 years of Jeremiah’s prophecy, really only about 68 years. Inasmuch as Christ presented himself officially as “Messiah-Prince” only once (Zech 9:9; cf. Mt 21:5. Contrast Mt 16:20; Lk 9:20, 21) at the beginning of his last week, those interpreters who favor the Triumphal Entry for the close of the 69 weeks appear to be on the right track. (Pfeiffer, C F: Wycliffe Bible Commentary. 1981. Moody or Logos)

it will be built again with plaza and moat even in times of distress (Nehemiah 4:8,16, 17, 18; Ephesians 5:16) (Nehemiah 6:15)

It will be built again with plaza and moat - See preceding discussion of plaza and moat.

Times (06256) ('eth; Lxx = kairos) refers to a time, such as a season or the proper time. Their efforts to rebuild the city of Jerusalem would be associated with a "season" of trouble as discussed below.

Distress (06695) (tsoq) describes oppression, trouble, i.e., a state of hardship, trouble, and distress brought on by external pressure. For example this word is used in of God "distressing" His people in an attempt to bring them to repentance and salvation, Isaiah recording...

Isaiah 29:2 And I will bring distress (tsoq) to Ariel ("lion of God" = name applied to Jerusalem), and she shall be a city of lamenting and mourning; and she shall be like an Ariel to me (NIV = "and she will be to me like an altar hearth."). (Comment: In this passage Jerusalem would be turned into an altar hearth because of the death and devastation to come.)

The book of Nehemiah (entire book)  gives ample testimony to the fact that the rebuilding of the city and the wall was associated with vigorous, even vicious opposition. Nehemiah records for example  that