As your Messianic rabbi friend seems to continue to live ignorant of basic Christian concepts he fails to grasp them perhaps because of he is blinded by Jewish ways and customs so much so that he misses the point (Christians do this often).
Well Kevin did realize that stuff. A much different guy away from his wife, who was bad news (like abusive narcissistic personality stuff and a pot stirrer as far as making problems).
A lot of the problem is the concept of "Reason for Existence" aka Raison d'être
Evangelizing the Jesus denying Jews is a slow process, where often little is visibly accomplished ; because that side has had nearly 2000 years to perfect all their arguments and rhetoric against the Gospel. So there is a secondary purpose of the movement, as far as being a light to the gentiles. In the case of today since that is largely already done it is to point out all the contextual stuff in the Bible as far as OT footnotes and other cultural back ground stuff. Which is fine, I go out of my way to read and look up that stuff myself.
But I think there is a lot of insecurity. Because in some ways their Reason of Existence is challenged. That they are not really accomplishing a lot etc. But mixed in with that their are lots of problems of not feeling they have much in common with your average non-Jewish believer etc.
And well their is lots and lots of hand wringing over the fact that the gentiles have mostly taken over the Faith so to speak. I'm talking about exaggerated claims that Anti-Semiticism is the main culprit.
I don't deny that has happened, but there are lots of factors etc. going on besides that, and I don't think Anti-Semiticism is the main cause.
1) In retrospect, I really believe that some kind of Messianic Judaism was never intended to be the main vehicle for evangelizing the world. In a nutshell, I believe Jesus gave the parable of the wineskins for a reason. I don't think that Messianic Judaism had what it takes to be "All things to all people" as Paul mentioned of himself. Koshur laws and customs get in the way of that. I believe MJ has a role now but that is more as "Treasurers old and new" goes (It helps people who are really stuck in their Jewish identity and gives some unique perspective to the Body of Christ) and on the Jewish side the liturgical synagogue prayers were eventually changed so believing Jews were forced out lest they be praying for their own damnation.
2) Most of the time when MJ's talk about Anti-Semticism, Church history etc. they frequently present a lop sided view, quite often they omit or gloss over things that I believe are extremely significant to the Church gradually becoming gentile, and the whole Christian vs. Jew dynamic that eventually evolves. I'm talking about things like the significance of Bar Kochba, the existence of heretical Jewish sects like the Ebionites (which would later help to inspire Mohammed), the nature of population growth as far as birth and evangelism (that favored gentiles), the general theology of the Church of the day that encouraged all believers to worship together to be One Body of Christ etc. (which would lead to pressure to move worship days over to Sunday etc. as the demographics of the Church changed etc.). Besides all that there was a lot of anti-gentile sentiment in the old days to go with the anti-semticism (lots of stuff in the Talmud against gentiles).
Anyway in psychology, I learned from the school of Alfred Adler that people often interpret the past in light of the present. I really believe that is the case in this situation. Essentially people are reading Church history in light of the Holocaust, Spanish Inquisition etc. They are reading it with jaundiced eyes. I don't deny that there are problems but they want to make Anti-Semiticism a grand unifying theory of why things are the way they are, and I don't believe that is accurate because lots of other stuff was going on besides that.