Remember the context of Gabriel's message - the decree is for Israel and Jerusalem.

John MacArthur rightly reminds us that God is not finished with Israel as is sadly taught in so many otherwise conservative churches...

Israel remains at the center stage of redemptive history. Despite the many issues facing modern society our focus is constantly drawn to the Middle East and the nation of Israel--a country smaller than the state of New Jersey. Yet despite its importance, when a well-known Bible teacher was asked about the significance of the modern state of Israel not long ago, he replied, "It has utterly no significance at all because God is finished with Israel as of the crucifixion of their Messiah. " (Ref)

In fact according to God's Holy Word, He is clearly not finished with His chosen people, Israel, despite the fact that the majority of Jews continue to reject saving belief in the Messiah...hear God's testimony to His faithfulness to keep His covenant promises...

For the LORD will not abandon His people on account of His great name (His name is everything He is, His attributes, His character, etc), because the LORD has been pleased to make you a people for Himself. (1Samuel 12:22)

Comment: "This crucial declaration makes abundantly clear the principle by which God was operating in behalf of Israel. God's program for the nation of Israel was never based upon the inherent worth or loveliness of Israel, but rather upon the sovereign disposition of God. God's continuing program for Israel is not dependent upon Israel's faithfulness to God, but upon God's faithfulness to His Word and to His purposes {Deut 7:6, 8}. Because of "His great name's sake," God will not forsake His people. In other words, God has announced a plan for Israel which He must accomplish, or else disparage His name by faithlessness {cf. Ezek 37:11} (Ref).

(The psalmist records God's affirmation) Ps 89:31 If they violate My statutes, And do not keep My commandments, 32 Then I will visit their transgression with the rod, And their iniquity with stripes. 33 "But I will not break off My lovingkindness from him, Nor deal falsely in My faithfulness. 34 "My covenant (see notes on Abrahamic Covenant - although in context this may refer specifically to the Davidic Covenant) I will not violate, Nor will I alter the utterance of My lips. 35 "Once I have sworn by My holiness; I will not lie to David. 36 "His descendants (remnant = those Jews who place their faith in Messiah) shall endure forever, And his throne (Jesus as David's greatest "Son" - in the lineage of David - will reign but Scripture also teaches that David himself will reign - see Ezek 34:24 which describes the "Greater David" and David who God will resurrect - Jer 30:9) as the sun before Me. 37 "It shall be established forever like the moon, And the witness in the sky is faithful." Selah. (Psalm 89:31-37)

For the LORD will not abandon His people (Israel), Nor will He forsake His inheritance (see Dt 4:20 where this same Hebrew word is used to refer to Israel as "His own possession"). (Psalm 94:14)

(God's faithfulness to keep His promises to Israel are repeated in the NT, Paul writing) I say then, God has not rejected His people, has He? May it never be! (the strongest negative statement possible = no way, not ever!) For I too am an Israelite, a descendant of Abraham, of the tribe of Benjamin.  God has not rejected His people whom He foreknew. Or do you not know what the Scripture says in the passage about Elijah, how he pleads with God against Israel? (Ro 11:1, 2 -See notes Ro 11:1; 2)

Comment: To take "Israel" out of the NT and "replace" it with the Church contradicts God's clear word of promise. See the related discussion of The Israel of God. The book of Revelation is all about God's promise to purge and restore Israel and it follows that if one says the NT Church is the "spiritual Israel", then it should come as no surprise that interpretation of that blessed last record of God's faithfulness becomes a virtual quagmire of gnarled incomprehensible comments that attempt to "wash" this final prophecy clean of a literal fulfillment. Little wonder that so many find themselves "dazed and confused" by a book, the very title of which signifies it is to be a "taking of the lid off". This "God is finished with Israel" approach also explains why the single greatest prophecy in the OT here in Daniel 9:24-27 is also one of the most fiercely debated and challenged passages in the entire Old Testament. To reiterate God is not finished with Israel and Daniel 9:24-27 and the book of Revelation both bear dramatic testimony of this truth! Let God's faithfulness to His rebellious people Israel give each of us encouragement and hope in our daily walks which are not always as "holy" as we would like them to be.

After ('achar) means afterward, later, some time later or following in time and pertains to a time subsequent to another time, in this case Messiah's being cut off subsequent to the 483 years, not during the Seventieth Week which therefore by default signal a time yet future and implies an interlude (or gap of time).

For example, 'achar is used this way in Genesis where Abraham says to his three visitors at Mamre

I will bring a piece of bread, that you may refresh yourselves; after that ('achar) you may go on... (Genesis 18:5)

The sixty two weeks - 7 weeks plus 62 weeks or a total of 483 years. After this time has passed the Messiah will be cut off which is clearly a reference to His crucifixion.

Gabriel states that after the sixty-two "sevens" plus the seven "sevens" or after sixty-nine "sevens" (483 years) the "Messiah will be cut off". Note that Gabriel does not say the Messiah will be cut off "at that time" nor does he say it occurs during the seventieth "seven" but "after" the sixty-ninth "seven".

Messiah will be cut off and have nothing

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).

Cut off (karath) means to sever an object from its source or cut into parts and implies a violent action. The Septuagint translates karath in Daniel 9:27 with the verb exolethreuo which means to be utterly destroyed (only NT use is Acts 3:23)

The first OT use of karath gives us a good sense of the meaning...

And I establish My covenant with you; and all flesh shall never again be cut off by the water of the flood, neither shall there again be a flood to destroy (karath) the earth." (Genesis 9:11) (see also same use Deut 20:20; Je 11:19; Ps 37:9)

Moses records God's instructions regarding idolatry writing that...

you are to tear down their altars and smash their sacred pillars and cut down (karath) their Asherim (Exodus 34:13)

MacArthur adds that...

Karath is used a number of times in the Old Testament to describe the execution of a criminal (Lev 7:20; Ps 37:9; Pr 2:22). Daniel's usage of the term implies the Messiah would die a criminal's death--a prophecy so specific, it seems incomprehensible that when Jesus was presented in triumph in precise accord with Daniel's timetable () but then crucified, the Jewish people would not immediately recognize who He was. They waited for centuries for their Messiah to come and then missed Him through hate and despite. And if it is argued that Daniel 9 is somewhat obscure and easily misunderstood, one need only turn to Psalm 22 (which describes the crucifixion in detail) or Isaiah 53 (which describes the suffering and death of the Messiah) to understand that the Old Testament clearly declares the Messiah would die. (Ref)

Almost every conservative evangelical source agrees this verse is clearly a reference to the crucifixion of Christ. Christ was indeed not only "cut off" from man and from life, but on the cross indicated that He was forsaken of God, crying out

My God, my God, why hast thou forsaken me? (Mt 27:46)

Isaiah records that

By oppression and judgment He was taken away; and as for His generation, who considered that He was cut off out of the land of the living, for the transgression of my people to whom the stroke was due? (Isaiah 53:8)

Nothing either `nothing' or `no one'. The exact meaning of this phrase is uncertain. Some interpret this as the desertion by His disciples (who fled at the time of his arrest and trial). Others feel that nothing that rightly belonged to Him as Messiah the Prince was given to Him at that time. In other words, He did not come into His full reward nor the exercise of His Kingly authority.

MacArthur explains this difficult to understand phrase this way...

When Jesus died on the cross He received nothing that was due Him: no honor, respect, love, or acceptance. "He was in the world, and the world was made by him, and the world knew him not. He came unto his own, and his own received him not" (John 1:10, 11). Instead He received what He didn't deserve: the sins of the world. (Ref)

The people of the prince who is to come will destroy the city and the sanctuary:

Who are these people?  Recall that Daniel has previously revealed four Gentile world empires that would have a great impact on the fate of Israel - Babylon, Medo-Persia, Greece, and Rome (see Daniel 2:31-43; 7:1-8 - click to study these passages charted out in parallel with Daniel 9:24-27). As discussed in those passages it becomes obvious that the  Roman Empire will be revived ("Revived Roman Empire" - this term per se does not appear in the Bible) again as a ten-nation confederacy during the last days. Thus the people of the prince to come will have some connection with the Romans and a revived Roman Empire.

How do we know? If one looks at the action of these people in destroying the city (Jerusalem) and the sanctuary (the Holy Jewish Temple in Jerusalem), the most obvious conclusion from history is that this event was fulfilled in the sacking and destruction of Jerusalem and the Temple in  70AD, which would identify the people as the Roman Empire led by the Roman General Titus. The prince who is to come would then be associated somehow with the Roman Empire or what has been designated by most evangelical commentaries as the "Revived Roman Empire". Observe carefully that this verse does not state that the prince comes at this time nor that the city is destroyed by him but by his people.

Donald Campbell notes that...

Leopold Cohn, a European rabbi, studied the prophecy of the 70 weeks and came to the conclusion, based on verse 26, that Messiah had already come because His coming was to be before the destruction had taken place in A.D. 70! Approaching an older rabbi, he asked where Messiah was. The rabbi said, "Go to New York and you will find Messiah there." Selling most of his belongings to buy passage to America, Mr. Cohn came to this country and wandered the streets of New York City, looking for Messiah. One day he heard singing coming from a building and went in, only to hear a clear gospel message. That night he received the Lord Jesus Christ as Messiah and Savior. Shortly after, Mr. Cohn bought a stable, swept it out, set up some chairs, and began to hold gospel meetings, the first outreach of what was to become the American Board of Missions to the Jews.  (Campbell, D. Daniel God's Man in a Secular Society)

Spurgeon has the following devotional on Daniel 9:26...

"The Messiah shall be cut off, but not for Himself." - Daniel 9:26  - Blessed be His name, there was no cause of death in Him. Neither original nor actual sin had defiled Him, and therefore death had no claim upon Him. No man could have taken His life from Him justly, for He had done no man wrong, and no man could even have lain Him by force unless He had been pleased to yield Himself to die. But lo, one sins and Another suffers. Justice was offended by us, but found its satisfaction in Him. Rivers of tears, mountains of offerings, seas of the blood of bullocks, and hills of frankincense, could not have availed for the removal of sin; but Jesus was cut off for us, and the cause of wrath was cut off at once, for sin was put away for ever. Herein is wisdom, whereby substitution, the sure and speedy way of atonement, was devised! Herein is condescension, which brought Messiah, the Prince, to wear a crown of thorns, and die upon the Cross! Herein is love, which led the Redeemer to lay down His life for His enemies!

It is not enough, however, to admire the spectacle of the innocent bleeding for the guilty, we must make sure of our interest therein. The special object of the Messiah's death was the salvation of His church; have we a part and a lot among those for whom He gave His life a ransom? Did the Lord Jesus stand as our representative? Are we healed by His stripes? It will be a terrible thing indeed if we should come short of a portion in His sacrifice; it were better for us that we had never been born. Solemn as the question is, it is a joyful circumstance that it is one which may be answered clearly and without mistake. To all who believe on Him the Lord Jesus is a present Saviour, and upon them all the blood of reconciliation has been sprinkled. Let all who trust in the merit of Messiah's death be joyful at every remembrance of Him, and let their holy gratitude lead them to the fullest consecration to His cause.

The people of the prince who is to come - Note that it is not “the prince who is to come” that does the destroying, but “the people” of that prince. "The city and the sanctuary" in context is clearly a reference to Jerusalem and the Temple, which were destroyed in 70ad by Roman troops led by Titus. Thus "the people" are identified as Roman and "the prince" will arise from the Roman empire.

As discussed in notes on Daniel 9:27 this prince is identical to the future Antichrist (the best known title of this individual but found only in one NT passage 1Jn 2:22)  and since Rome has long disappeared from world history, his origin must be from a revived Roman empire (See Dr Walvoord's article - Revival of Rome).

Beloved though believers are instructed not to ignorant of the evil one's schemes lest we be taken advantage of, we as the Bride of Christ must not become side-tracked or distracted from our call to continually, eagerly, longingly be on the look out for the imminent return of our Bridegroom, the Lord Jesus Christ. Believers are to be looking for the Christ, not the Antichrist!

An older commentary from the 1800's by Adam Clarke (1762-1832) gives the following interpretation of the prince who is to come...

By the "prince" Titus, the son of Vespasian, is plainly intended; and "the people of that prince" are no other than the Romans, who, according to the prophecy, destroyed the sanctuary. (Comment: Clearly I disagree with Clarke's rather dogmatic interpretation, but present it so that the discerning reader is alerted to the fact that many of the "older" commentaries are often not good resources to aid one's interpretation of Bible prophecy. And yet since these are virtually all public domain, they are the most common free resources on the Internet. Be a Berean!)

Pfeiffer sums this up commenting that

"These considerations show that the idea of a gap in the weeks at this point is a matter of exegesis (from Greek exegeomai meaning "to draw out" and so is the process of careful, analytical study of the biblical text, usually verse by verse, phrase by phrase, in order to explain or interpret the passage). Considerations of theology are not primarily involved...Let us stay by what the passage says." "Amen!" (The Wycliffe Bible commentary: Old Testament : Moody Press)

Destroy the city and the sanctuary -

In Luke 21 Jesus had given a prophetic warning concerning the coming destruction of Jerusalem declaring...

But when you see Jerusalem surrounded by armies, then recognize that her desolation is at hand. 21  Then let those who are in Judea flee to the mountains, and let those who are in the midst of the city depart, and let not those who are in the country enter the city 22  because these are days of vengeance (Lev 26:25 'I will also bring upon you a sword which will execute vengeance for the covenant; and when you gather together into your cities, I will send pestilence among you, so that you shall be delivered into enemy hands...28 then I will act with wrathful hostility against you; and I, even I, will punish you seven times for your sins. 29 'Further, you shall eat the flesh of your sons and the flesh of your daughters you shall eat. {This prophecy was literally fulfilled in the lengthy siege of Jerusalem. Josephus gives a dreadful detail of a woman named Mary, who in the extremity of the severe famine killed her nursing baby and had cannibalized a part when discovered by Roman soldiers!}), in order that all things which are written may be fulfilled. 23 Woe to those who are with child and to those who nurse babes in those days for there will be great distress upon the land and wrath to this people (Those who tried to escape or terrorize the enemy were frequently captured and crucified--often 500 were nailed to crosses on a given day. The forests {"distress upon the land"} around Jerusalem were completely destroyed to supply the wood necessary for battering rams, ramps, catapults, camp fires, ladders, and the many crosses that rose outside the city. See note below regarding believers who did escape.), 24 and they will fall by the edge of the sword and will be led captive into all the nations; and Jerusalem will be trampled under foot by the Gentiles until the times of the Gentiles be fulfilled. (Luke 21:20-24)

Comment: See "Times of the Gentiles" in the chart entitled "God's Plan for Jerusalem". In context, the sign of Jerusalem surrounded by armies was a warning of the future siege {which apparently went on for some 143 days} of Jerusalem by the Roman General Titus in A.D. 70, a siege which would preface the complete destruction of Jerusalem and the Temple. Unbelief might have argued that with a besieging army outside the walls, escape would be impossible; but God's Word never fails. As recorded by Josephus  {Wars 2.539-540}, the Roman armies withdrew for a short season {Josephus says "without any just cause" expressing some confusion as to why the withdrawal - of course God is sovereign and by faith we see that surely He orchestrated this brief hiatus allowing believers to escape!}, thus giving the believing Jews the opportunity to escape.  For those who heeded Jesus' warning this was clearly the signal to flee the city. This they did and went out to a place called Pella, a little town east of the Jordan near the Sea of Galilee, where they were preserved as recorded by the historian Eusebius. The Jewish historian Josephus recorded that nearly a million people were killed by the Romans, and over 100,000 taken captive. This historically verifiable "holocaust" is but a faint picture of the yet future "holocaust", that Jesus explained in Matthew 24:15 concerning the abomination of desolation standing in the Jewish Temple.)  (For an even more detailed description of the horrific scene in Jerusalem in 70AD click here for John MacArthur's discussion).

As an aside, did you note God's warning in Leviticus 26:28 of seven times more punishment? Recall that the Babylonian exile lasted 70 years and yet even after returning to Jerusalem, the post-exilic Jews continued in rebellion. So here in Daniel 9:24-27, we see the fulfillment of God's prophecy of judgment in that seven times seventy (years in Babylonian exile) is 490 years, the exact number specified in Daniel 9:24 for the Jews and Jerusalem ("your people and your holy city")! And when this final indignation and purging of Israel has run its full course, all of saved Israel will enter the promised Messianic Kingdom. This is a succinct recap of God's Plan for Israel!

And its end will come with a flood; even to the end there will be war; desolations are determined : (Matthew 24:6, 7 , 8, 9, 10, 11, 12, 13, 14; Mark 13:7) (Da 11:10; Is 8:7; Je 46:7; Amos 8:8; 9:5; Nah 1:8)

And its end will come with a flood - The desolations to be visited on Jerusalem will be as destructive as a raging flood, which is probably being used metaphorically, picturing for example sudden destruction.

even to the end there will be war; desolations are determined -

Israel has experienced a steady stream of desolations that began with the destruction of Jerusalem in 70AD, including the Medieval Crusaders (many of whom were more like "mid-evil" for they challenged Jews to convert or die! - Click and scroll down to "Crusades"), the Spanish Inquisition, the Russian pogroms, Hitler's insane Nazi holocaust. And yet the rise of the Antichrist will commence a holocaust beyond any Israel has previously experienced. (Re 12:13, 14, 15, 16, 17 - See notes Re 12:13; 14; 15; 16; 17, where the woman is clearly Israel). That final desolation is vividly prefigured by the first Roman "holocaust" in 70AD.

The end is a phrase that is used numerous times in Daniel to refer to the end of this age (see below) and therefore comparing Scripture with Scripture, it seems very appropriate to take the use in this verse as a reference to the end of this age.

Da 8:17 So he came near to where I was standing, and when he came I was frightened and fell on my face; but he said to me, "Son of man, understand that the vision pertains to the time of the end."

Da 8:19 And he said, "Behold, I am going to let you know what will occur at the final period of the indignation, for it pertains to the appointed time of the end.

Da 11:27 "As for both kings, their hearts will be intent on evil, and they will speak lies to each other at the same table; but it will not succeed, for the end is still to come at the appointed time.

Da 11:35 "And some of those who have insight will fall, in order to refine, purge, and make them pure, until the end time; because it is still to come at the appointed time.

Da 11:40 "And at the end time the king of the South will collide with him, and the king of the North will storm against him with chariots, with horsemen, and with many ships; and he will enter countries, overflow them, and pass through.

Da 12:4 "But as for you, Daniel, conceal these words and seal up the book until the end of time; many will go back and forth, and knowledge will increase."

Da 12:9 And he said, "Go your way, Daniel, for these words are concealed and sealed up until the end time.

Da 12:13 "But as for you, go your way to the end; then you will enter into rest and rise again for your allotted portion at the end of the age."

Harry Ironside feels that

These words briefly describe the history of Palestine from the coming of the Roman armies under Titus to the present time. Jerusalem, and Palestine as a whole, have been trodden down of all nations, and shall be, ‘until the times of the Gentiles be fulfilled.

The phrase "desolations are determined" once again indicates that God knows where history is going.

even until a complete destruction, one that is decreed, is poured out on the one who makes desolate -

From this verse we can see that "the one who makes desolate" is the same one who made and then broke the seven year covenant, and is without doubt the Antichrist whom Jesus warned about declaring

"when you see the ABOMINATION OF DESOLATION ("the abomination that causes desolation", NIV) which was spoken of through Daniel the prophet, standing in the holy place (let the reader understand)...21 for then there will be a great tribulation, such as has not occurred since the beginning of the world until now, nor ever shall." (Mt 24:15,21)

The breaking of the covenant and desolation of the temple will signal the beginning of the end of this age, the times of the Gentiles and the onset of the last three and one-half years of God's wrath as described in Revelation, beginning in Re 11:14 through Revelation 19:21.