Now that we've discussed that prophecy is:
Prophets who do give visions of the future fall into two categories. A positive vision will always come to pass (eventually). However negative visions may always be avoided by improving one's behavior. This is the purpose of a negative vision -- to warn people to avoid it.
A principle of the Talmud that Rashi quotes several times states that אֵין מִקְרָא יוֹצֵא מִידֵי פְשׁוּטוֹ -- in English this would be "A verse cannot depart from its plain meaning." (Treatise Shabbat 63a, Treatise Y'vamot 11b, 24a; quoted by Rashi at B'réshıt / Genesis 15:10, 37:19, Sh'mot / Exodus 12:2).
Judaism is known for its rich history of story telling to make a moral point. This is called "Midrash Aggadah" -- where a word or sentence is lifted from the bible to make a moral point. However, prophecy is NEVER based on these flights of fancy. Prophecy is always based on the plain meaning of the text (which is why, for example, the prophet Isaiah's message to King Ahaz in Isaiah 7 has nothing to do with a future virgin birth 700 years later of Jesus). The message is for the then living king, which is clear when the passage is read in context.
Christians can't rely on the plain meaning of future visions to "prove" that Jesus fulfilled prophecies, so they invented the idea of "types and shadows," or very non-literal readings where they just take a word or sentence out of context and claim that Jesus fulfilled something even when the text is plainly not discussing Jesus.
This missionary concept of types and shadows for "prophetic fulfillment" is not justified. It is alien to the Biblical view. When the T'nach identifies a vision as fulfilled, we see a direct one-to-one correspondence between prophecy and fulfillment. For example:
"Joshua caused [the people] to swear at that time saying, 'Cursed before G-d is the man who rises up and builds this city Jericho. With his firstborn son he will lay its foundations, and with his youngest he will set up its gates' (Joshua 6:26)."
We read of the fulfillment:
"In his days, Hiel the Beth-elite built Jericho; with Abiriam, his firstborn, he laid its foundations; and with Segub, his youngest, he set up its doors, according to the word of G-d He spoke through Joshua son of Nun (I Kings 16:34)."
We see that plain meaning is clearly predictive, the opposite of the missionary method of hints, things lifted out of context and "shadows."
Let's look at an example where Jesus does not fullfill the p'shat (plain meaning):
Types and shadows are just an excuse because clearly Jesus does not actually fulfill the plain meaning of the prophets. The concept of "dual prophecy" (that a vision in the T'nach happened "way back when" but that it also pertains to Jesus) is likewise not biblical. It, too, was an attempt on the part of missionaries to paint Jesus into text where he clearly does not fit.
This blog will focus on discussing each of the supposed 365 prophecies about Jesus one by one, showing what they are really about and proving that they do not prophetically foretell Jesus as the messiah.
Rabbi Michael Skobac, a rav with Jews for Judaism (a wonderful resource) has been conducting podcasts with Jono Vandor of Truth2U.org. They have been discussing the 365 Prophecies weekly. You can find recordings of these sessions at Truth2U's 365 Messianic Prophecies page.