One of his talmidim, Rabbi Hillel Shklover wrote a book called “Kol HaTor”, which has been translated into English as “Voice of the Turtledove”. In it he speaks of two mashiachs: Mashiach ben Yosef and Mashiach ben David. The job of Mashiach ben Yosef is gathering in the exiles and building the material aspects of EY (Rav Kook sya in his eulogy for Herzl, “Misped b’Yerushalayim” printed in “Maamarei HaRaya”) thatt his leads to an antipathy towards Tora as Mashiach ben Yosef concerns himself exclusively with material matters (Rav Kook held that Herzl or the secular Zionist movement in general was Mashiach ben Yosef). The job of Mashiach ben David is buiding the spiritual aspect culminating in the Bet HaMikdash. He also says that the Gra said that in the time before Mashiach (ikveta d’Mashicha) the sin of the Spies will affect many who learn Tora and love Galut (see also “Em HaBanim Semeicha”, which has also been translated into English). He also states that whereas Mashiach ben Yosef will give way to Mashiach ben David he may or may not actually die depending on whether or not Am Yisrael davens for him. I do not know if he discusses the Holocuast but the Gemara states that a ruler will arise who decrees are worse than those of Haman (Sanhedrin 97b). This could refer to the designer of the Holocaust (see Megilla 6b that if not fore Hashem restraining them “Germamia” would destroy the world – Rav Yaakov Emden says that it is “our Ashkenaz” and the Gra says that it should read “Germania”) who decreed against both Jewish lives and Jewish religious practices and planned to also outlaw Natzrut because of its Jewish origins).
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