Jacob recently responded to the question of Jesus and the donkeys as recorded in the Gospels:

The two donkeys fulfill the Messianic prophecy of Zechariah 9:9. The riding on the donkey "lowly" as a King contrasts to the fact that Kings rode horses.In His first coming, although a King, Jesus comes meek and lowly as a sacrifice for sin. In His second coming He arrives as a conquering King mounted on a horse (Revelation 19:11).

This corresponds to the two conceptual pictures in Judaism of the Messiah as Ha Moshioch Be Yosef (Messiah Son of Joseph prefigured by Joseph in the Book of Genesis) also known as "Ben Ephraim" and identified with the suffering servant of Isaiah 52 and 53, This is the the first coming on a donkey. The Second coming is Ha Moshioch Ben David (Messiah Son of David), the conquering King who establishes the millenial kingdom in the character of King David.

Moriel has a teaching explaining this in depth: One Messiah, Two Comings. (This can be read online here or a DVD of the sermon obtained here.)

Regarding the two donkeys, only Matthew's version records two for which there are different proposed explanations. The best may be that Zechariah was using repetitive poetry (they were therefore to be the same animal). Because it was a baby donkey ("onen" in Greek) it had not been ridden on yet, so the mother ("polon") was brought along to accompany it so as not to separate it from its mother.

In sending for the donkeys Jesus may have been exercising the legal right of "agerion" ‚  "” or commandeering ‚  "” that could be used by either a King or a rabbi (Jesus being both, hence two donkeys).

I trust this helps.

In Jesus,

Jacob Prasch

The original sender asked the follow-up question:

I am well aware of Messiah Ben Joseph/Suffering Servant and Messiah Ben David/King (or Ephraim) as it relates to messianic prophecy. But I have a further question about the two donkeys. Do you see in the two donkeys an allusion or typology of Jesus moving from Old Covenant to New Covenant? I was given an audio message from a pastor who explained the presence of two donkeys was unique to Matthew's gospel because a particular allusion was made to Jesus transitioning from first offering the Gospel to the Jews (older mother donkey) and then once refused, moving on to the new younger donkey of the church. This is not to imply a replacement theology but simply that Jesus was moving on to a new work, the church. Ever hear of that? Do you think that is a credible interpretation?

Jacob replies:

The two donkey/two covenant thing is speculative and without synoptic support or cognate text support.

Midrash tn the time of Jesus and Paul worked by the Midoth of Rabbi Hillel (grandfather of St. Paul's tutor Gamaliel). The second principle is "Binyan Ab M'Shna Ketubim", building a typological parallel from two texts to mutually illuminate eachother with the same exegetical and typological considerations applying to both.

In other words one would have to find at least one other biblical text where two donkeys work in tandem and where a symbolic or metaphorical use of a donkey was overtly ascribed to a covenant.

Additionally, if one existed, for instance, in the Old Testament one would then need to see if the Greek term in the Septuagint (either "polon" in Greek or whatever) translated the varied Hebrew term "hamor", "arad", "pered", "ayir" or "athon" as the same Greek word or words used in the Triumphal Entry narrative text of Matthew. In fact, however, there is none.

Donkeys are used to illustrate different things in Scripture, but there is not a single instance or context where a donkey overtly represents covenant as, for instance, "Living Water" represents the Holy Spirit, or "fruit" represents the fruit of the Sprit, or an altar represents the cross, etc.

The kind of thing you describe is at best application; but if one sought some doctrinal basis based on the speculation (I am not suggesting the tape you refer to does that as I have not heard it) it would lean towards a Gnostic hermeneutic which is wrong.

People can assign a figurative or symbolic meaning to almost anything (and Gnostics do so not merely to illustrate doctrine but to base doctrine on it, which always leads to serious doctrinal error). There must be a corresponding text in context addressing the same issues and using the same figures of speach or types where the symbolic meaning is not nebulous.

I trust this helps.

In Jesus,

Jacob