Messianic prophecy

Messianic prophecy in Christianity refers to a collection of claims that the events in the life of Jesus represent the fulfillment of prophecies from Judaism. There is, as one would expect, considerable disagreement between Jews and Christians regarding which passages qualify as prophecy and which, if any, of the prophetic requirements for the 'moshiach', or messiah, were met by Jesus.

Jewish Messianic Prophecy
While Judaism is divided into Orthodox, Conservative and Reform branches, each with its own views, the belief that the moshiach (anointed one) will eventually appear is one of the 13 principles of faith, as expressed by noted Jewish scholar, Rabbi Moshe ben Maimon:

Specific attributes of the Jewish moshiach
A complete discussion of this subject can be found at the Judaism 101 site. In summary, the Jewish view of a moshiach is that of a fully human man who is well versed in Jewish law and will serve as a charismatic leader and warlord who will win many battles for Israel.

If Jesus existed and the New Testament contains an accurate record of his words and deeds, he does not fit this view of a messiah.

Christian Messianic Prophecy
Christians have their own claims of prophecy that different from those of the Jews. This presents the outsider with a very difficult question:

"If Jesus is the Jewish messiah, why are the Christian claims of prophecy so dramatically different from those of the Jews?"

The number of prophecies claimed by Christians varies greatly. While some Christians may simply aver that Jesus "fulfilled all prophecies", others attempt to enumerate and specify which prophecies they believe have been fulfilled. It is a trivial matter to find websites espousing hundreds or even thousands of fulfilled prophecies.

Among more scholarly apologists, the number of fulfilled prophecies is still often noted as being in the hundreds. Josh McDowell, in his famous apologetic work Evidence That Demands a Verdict includes dozens of messianic prophecies which he claims have been fulfilled.

Counter-Apologetics
Claims of fulfilled prophecy need to meet certain criteria in order to be considered evidence of divine revelation.

First, they should be clearly understood to be prophetic before any claim of fulfillment is presented. It is a trivial matter to match events to ambiguous passages and claim that the passages were prophetic. We tend to find hidden meaning wherever we seek it and flimsy correlation that should realistically be viewed as unrelated coincidence is often attributed as causally or prophetically related.

Second, predictions should represent knowledge that the prophet should not have access to and should involve something beyond the mundane so that the fulfillment of the prophecy demonstrates that the source of the prophecy transcends the prophet. Predicting that the sun will rise tomorrow may have a very high success rate, but it's hardly the sort of thing we should consider as evidence of any supernatural source of prophecy.

Third, regardless of how unclear or poorly understood the prediction is at the time it is made, it should be clear enough that the fulfillment should be obvious. Victor J. Stenger in his book, God: The Failed Hypothesis explains:

Claims of fulfilled prophecy in the Bible suffer from other problems:
 * Knowing about a prophecy may encourage people to work to fulfill it.
 * This is akin to claiming that the waiter fulfilled my prophecy by bringing me what I ordered.
 * Other religions with contradictory beliefs also claim fulfilled prophecy
 * The claims that particular prophecies have been fulfilled are unverifiable. One must begin with the assumption that the Bible is an accurate record of both the prediction and its claim of fulfillment.
 * In addition the inability to verify these claims, we have the added problem that the Bible we have today is the result of both a selection bias (Church leaders picked the books and versions that best matched what they believed to be true) and scribal alteration.

Any sufficiently ambiguous passage can, after the fact, be viewed to be prophetic. Many are convinced of the prophetic abilities of Nostradamus, yet none of those predictions meet the requirements we would impose in order to establish that the claim of fulfilled prophecy is anything more than chance or the wishful thinking and careful rationalization of those who wish to believe.