Question;:
An atheist friend of mine claimed that there a many contradictions or prophetic misinterpretations in Matthew.  What is your response.  The list is Matthew: 1:22-23, 2:15, 2:23, 8:16-17, 12:18-21, 12:23, 12:40, 16:4, 24:44, 27:9.
Answer:
These are really rather common and in my opinion fairly shallow criticisms of the Bible.  Here are my responses.
I do not see a contradiction in Matthew 1:22-23.  The Hebrew of Isaiah 7:14 was translated by the Jews themselves as "virgin" for the obvious reason of the context, which is that this is a wonder.  It is a prophecy of the Messiah fulfilled by Jesus.  Of course, it is one of the weaker examples we can use because, unlike many of the messianic prophecies fulfilled by Jesus, it is really hard to "prove" that the birth of Jesus was from a virgin.  I suppose all we really have is the word of Mary on this.
Matthew 2:15   I do not see what the contradiction is here.  Some have said that Matthew is pulling Hosea 11:1 out of context.  I believe that this is because they do not understand how  the Jews used the Old Testament.  Some messianic prophecies were of a definite historical nature.  Others are historical foreshadows.  For example, when God freed his people from Egypt, using Moses as his instrument in that case, it was a physical foreshadow of the spiritual fulfillment as God calls spirtiual Israel, the church out of spiritual slavery "in Egypt." through the second Moses; Jesus Christ.  It just so happens (not a coincidence) that Jesus literally came out of Egypt as a child, but this is not the main point of Matthew or of the original Hebrew writer.  It is a misunderstanding of the intent of the passage which causes skeptics to mistakenly charge Matthew of taking this prophecy out of context.
Matthew 2:23   Again, this is a rather shallow example which is often used by atheists, but a simple knowledge of Hebrew prophecy makes the meaning clear.  Jesus was called the Nazarene in three senses.  First of all, he was literally a Nazarene.  Second of all, he was by type/antitype an Nazirite.  However, it is in the third sense that Matthew is telling us Jesus fulfilled this prophecy.  The Hebrew word Nazar means branch.  There is more than one prophecy in the OT that the Messiah will be the "branch."  Specifically, he will be the branch of Jesse–the father of David.  In other words, the prophecy that Jesus would be the branch is a prophecy that he will be descended from David.  One example of a prophecy fulfilled by Jesus in this sense, as mentioned by Matthew is Isaiah 11:1.  Other prophecies calling the Messiah “the Branch” include Jeremiah 23:5, Zechariah 3:8 and Zechariah 6:12.  Again, this charge that Matthew is mistaken is a result, not of an error by Matthew, but of a shallow reading of the gospel.
Matthew 8:16-17.  I do not see the problem here.
Matthew 12:18-21    Jesus rather obviously did fulfill this prophecy.  What is the criticism here?
Matthew 12:40  Jesus did fulfill the physical prophecy of the death and resurrection of Jonah from the big fish.  Of course, if one takes a purely naturalistic viewpoint, the story of Jonah is impossible, but if we are deciding whether the Bible is true, to take as an assumption that there is no supernatural, that is to decide the result before doing the investigation, which is circular reasoning.  Even if the story of Jonah was a fable, which I believe it is not, then Jesus still did fulfill the prophecy of Jonah, both in offering salvation to the Gentiles, as did Jonah and in being resurrected from the dead. 
Matthew 16:4.   Jesus certainly did give the sign of Jonah when he was resurrected from the dead.  I believe the evidence for this resurrection is quite strong–but that is another argument to be made.
Matthew 24:44  I do not see a contradiction or problem here.
Matthew 27:9   Jesus fulfilled the prophecy in Zechariah 11:9-13.  Because this is really rather nice proof that Jesus is the promised Messiah, I am a bit surprised that a skeptic would be so bold as to bring up this one.
John Oakes, PhD

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