The other reason why this dispute is so confrontational is because the Christian affirmation that Jesus was the Messiah is a negation of Judaism, whereas Judaism's assertion that the Messiah has not arrived is a negation of Christianity.
With that in consideration, let's get back to the actual fulfillment of the prophecies. I want to make the argument simpler, and thus make the question simpler: "Were the Messianic prophecies fulfilled?" I don't want to get into who allegedly fulfilled the prophecies, simply if they were fulfilled. I will, however, add comments specific to Jesus since they have bearing on the conversation. Therefore, if the claim is that the prophecies in תַּנַ"ךְ were fulfilled, that means the criteria have to be in the תַּנַ"ךְ. That means that you cannot add any new criteria to the list or make up any. Otherwise, you would negate your own thesis. After listing the criteria, you need to acquire the answer to fulfillment by consulting history. Let us take a look at the authentic Messianic prophecies:
1) Genealogical. The Messiah must be descended from the House of David (Jeremiah 33:17-20, 1 Chronicles 17:11-12). Under Jewish law, lineage is traced through the biological father (Numbers 1:18-44, 34:14, Leviticus 24:10). According to the Christian New Testament, Jesus was born of Immaculate Conception (Matthew 1:18), which means Jesus had no biological father. Having no biological father means that you cannot be considered as a candidate for the Messiah. You can’t use Joseph as Jesus’ father because he was adopted, and the genealogy thus cannot be passed through adoption. But for argument’s sake, let's give Christians yet another benefit of a doubt and use Joseph for a moment. The Christian New Testament has two genealogies for Jesus, one from Matthew (chapter 1) and one from Luke (chapter 3). Not only can these two not agree on who Jesus’ [adopted] grandfather was, but more glaringly, there are an additional fifteen generations in Luke’s version that are not in Matthew’s! Plus, these two genealogies conflict with the account of David's actual genealogy given in Chronicles 1:3. If the Christian New Testament were a divine text, I would question its veracity based on this discrepancy. This is particularly ironic since Paul says that we should avoid foolish genealogies (Titus 3:3, 1 Timothy 1:4). Furthermore, this is very problematic for Christendom because this is the only authentic messianic criterion that Christianity claims that Jesus actually fulfilled.
2) Bringing the people Israel out of exile and back to the land of Israel (Isaiah 11:12, 27:12-13, Jeremiah 33:7). Jesus could not have possibly have fulfilled this prophecy since the people Israel were still living in Israel during his life. What’s more is that the people of Israel were expelled from the land shortly after Jesus’ death. It is difficult for an alleged Messianic candidate to have brought people back from exile when they were not even in exile in the first place. Even today, approximately 60% of Jews are still in exile, so to say that this prophecy has ever been fulfilled is inaccurate.
3) Building of the Third Temple (Ezekiel 37:26-28, Micah 4:1, Isaiah 2:2-3). During Jesus’ lifetime, the Second Temple was still standing, and shortly after Jesus’ death, the Second Temple was destroyed. To this very day, there still is no Third Temple, and we are thus awaiting its construction.
4) Universal peace (Isaiah 2:4, Micah 4:3, Ezekiel 37:26). Jesus himself did not embody this prophecy when he said that “he didn’t come to send peace but the sword (Matthew 10:34).” Even if you were to contend that the verse is taken out of context, it doesn’t matter because all you have to do is open a history textbook and a newspaper to know that universal peace has not come to mankind during any point since the prophecy has been made.
5) Universal knowledge and recognition of G-d (Isaiah 11:9, 40:5, Zephaniah 3:9, Jeremiah 31:33). Christians will claim that over two billion people are Christians. This ignores the fact that the other five billion people in the world are not Christian. They also have forgotten that they are claiming that they are fulfilling תַּנַ"ךְ, which means that the divinity in reference is Infinite Oneness, not some triune deity (please see Zechariah 14:9). Since not everybody in the world is a pure monotheist, this is yet another prophecy has yet to be fulfilled.
Christian apologetics will contend that the "peace" is in our hearts and that Israel is not an earthly kingdom, but a heavenly kingdom. We have to remember that if Christians are claiming to have fulfilled a certain text, the criteria have to come from that particular text, or they are actually fulfilling something else. Much to a Christian's dismay, both the universal peace and the prophecies referring to Israel are very much in reference to this world, not some otherworldly realm.
A similar argument can be made for Jesus supposedly fulfilling these during a Second Coming, which comes with its own problems. For one, there is no mentioning of a Second Coming in the תַּנַ"ךְ. Second, this notion is strictly a Christian one, one that seems to be derived from, as Rabbi David Wolpe puts it, a Christian disappointment in Jesus' death and a theological compensation for Jesus' failure to redeem the world [as Messiah]. Third, we are technically dealing with Jesus' third coming. The first coming covers the period prior to Jesus' death and the second coming spans the period from his alleged resurrection to his alleged ascension. Fourth, this would subsequently discredit Jesus' first coming. Anybody can round up religious disciples, and upon death, claim that they are going to be resurrected in the Second Coming. In all sincerity, either you or I could make that claim! Finally, the Christian New Testament reports that Jesus' return would be imminent (Matthew 16:28, 24:34, Luke 21:31-32, Mark 13:30), i.e. within the lifetime of Jesus' contemporaries. The passing of nearly two millennia without Jesus' return further enfeebles the Christian argument that Jesus was the Messiah.
Postscript: Christians claim the Jesus has fulfilled the Messianic prophecies according to תַּנַ"ךְ, which means that they are de facto claiming that they have fulfilled Judaism. In order to do that, they need to prove that these prophecies have been fulfilled according to תַּנַ"ךְ, and subsequently according to Judaism. As illustrated, we have yet arrived at the point in time in which we can say that the Messianic prophecies have been fulfilled. Any Christian attempt to explain this glaring reality away has to concoct responses that are separate from the authentic Messianic prophecies, meaning that they are fulfilling something else rather than תַּנַ"ךְ. By using such responses as the Second Coming or that "Israel is in reference to an otherworldly realm," Christians are not responding with evidence. As Rabbi Mordechai Becher puts it, "They are answers because the evidence go against the thesis [that Jesus was the Messiah]. You can't bring me 'proof' from an answer you are making up (i.e., it is not one of the criterion laid out in the Hebrew Scriptures) in order to deal with contrary evidence." In summation, Christians have underminded the very thesis they hold dear and have come up with these theological acrobatics to attempt to justify their belief in a failed messiah. The fact of the matter is that an ample look at Scriptures proves indubitably that we are still waiting for the day that these prophecies are actually fulfilled, and let's hope that they are fulfilled sooner rather than later.
For further information on the topic, please consult the following sources:
- Faith Strengthened, a website that copiously refutes Christian claims
- Jews for Judaism, an anti-missionary organization with superb sources
- 26 Reasons Jews Don't Believe in Jesus, a great book where the title speaks for itself
- The Real Messiah by Rabbi Aryeh Kaplan
- Why Jews Don't Accept Jesus, an article written by Conservative Rabbi Daniel Wolpe
- Why Jews Don't Believe in Jesus, an article written by Orthodox Rabbi Shraga Simmons
- Outreach Judaism, an anti-missionary organization started by Rabbi Tovia Singer
- The Hebrew Scriptures, in the original Hebrew