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In the Pesikta Rabbasi 36, brought in Yalkut Shimoni on Nach 499, it says:

שנו רבותינו בשעה שמלך המשיח בא עומד על גג בית המקדש והוא משמיע להם לישראל ואומר ענוים הגיע זמן גאולתכם

Our Rabbi's taught, at the time that the king Mashiach comes, he will stand on the roof of the Beis Hamikdash and will say to all Israel: "Humble people, it has reached the time of your redemption." (my translation)

  1. Why will Mashiach stand on top of the Beis Hamikdash specifically?
  2. Why will Mashiach be speaking to the humble people?
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  • Could you imagine how many people won't initially believe Mashiach has a PhD??
    – Double AA ♦
    Aug 18, 2021 at 17:13
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    Humble people is a title for all of Israel (so he's speaking to everyone, not specific people). The general idea here is that even when the full redemption has come, there's a mikdash and the Mashiach and everything, Israel may still doubt that it happened. Kind of like היינו כחולמים.
    – Harel13
    Aug 18, 2021 at 17:14
  • @Harel13 More specifically, it's just a reference to לְבַשֵּׂר עֲנָוִים he.wikisource.org/wiki/… which is just a few verses after the one that this Midrash opens with.
    – Double AA ♦
    Aug 18, 2021 at 17:16
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    Let's not forget that midrashrim aren't necessarily literal. You probably mean to ask what is the Midrash trying to teach with this accounting of events.
    – robev
    Aug 18, 2021 at 18:21
  • This could be a case of an ancient, pre-destruction tradition. The idea of a Messiah predates the Second Temple and was very popular throughout its days. Accordingly, the Messiah is supposed to override many existing practices/laws and him standing on the roof of the Temple does not seem inappropriate for Messianic times.
    – Al Berko
    Aug 18, 2021 at 19:34

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This question is dealt with explicitly in the talk by the Lubavitcher Rebbe published in the kuntress titled, B'Inyan Mikdash Me'at Zeh Beit Rabbeinu she'b'Bavel on the 28th of MarCheshvan 5752, page 419. See note 38 for details.

The essence of this is that the roof mentioned in the midrash is referring to the area that is not Kodesh and thus alludes to the Temple outside of Israel. This is the synagogue of the leader of generation.

The distinction of the people Israel, like is discussed at length in the kuntress, is also the distinction of the leader of that generation, who is Moshiach.

Like Moshe, the most distinguishing characteristic of Moshiach is his level of humility. This humility is the primary quality of the Jewish King. That in spite of being head and shoulders above everyone in the nation, he is completely subservient to his subjects in preserving and protecting their well being.

And since the Nasi (the leader of the generation) is equated with the whole generation, he actually demonstrates their defining quality too.

This last idea is one of the inner meanings behind the wording of the prayer said on the three Festivals after reciting the 13 attributes of Mercy before bringing out the Sefer Torah. That G-d should "fulfill in us the text that His Spirit should rest upon him..." is a reference from Navi to Moshiach specifically.

To appreciate this fully, the entire talk should be studied carefully including all the sources referenced.

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