“Moshiach saw his forefathers, worshipers of idols, and he parted from their ways and became a servant of the Alm-ghty, hidden away in Gan Eden.” In this respect, when “G-d returns the captives of Tziyon,” Moshiach will be among them and he will reign over his nation. * From Chapter Fifteen of Rabbi Shloma Majeski’s Likkutei Mekoros, Volume 2. (Underlined text is the compiler’s emphasis.)
Translated by Boruch Merkur
If I were to interpret it literally, I am inclined to say that in that case Moshiach dies because of the inequity of his generation. Moshiach is separated from the wicked horde and his soul is placed in the Supernal Gan Eden, like “the mighty men of old, the men of renown.”
The latter becomes the basis for interpreting the teaching of our Sages: Nine entered Gan Eden in their lifetimes; they entered Olam HaBa after having lived short lives, ascending to Heaven before their time, in order to separate from the [wicked] people of their generation. Thus, the L-rd remembered [the plight of] Chanoch and took him from the world prematurely to prevent him from succumbing to the allure of the sin of the degenerate generation he was in.
The same principle applies to the concept of Moshiach’s untimely death (sh’meis b’naaruso): G-d sought to remove Moshiach from the debasement of his time. Thus, it is within the context of discussing those who entered Gan Eden that our Sages said, “And why is Moshiach brought back? For he saw his forefathers, worshipers of idols, and he parted from their ways and became a servant of the Alm-ghty, hidden away in Gan Eden.” In this respect, when “G-d returns the captives of Tziyon,” Moshiach will be among them and he will reign over his nation.
Now, do not be puzzled by the fact that Melech HaMoshiach will be one of those who rises in the Resurrection, for the question was already raised in Perek Cheilek: Rav Asi said: “If he is among the living, it is someone like Rabbeinu HaKadosh. If he is among the deceased, it is someone like Daniel Ish Chamudos.”
( From Chapter 1 of Rabbi Don Yitzchok Abarbanel’s Yeshuos Meshicho)