Q: It is written that when Mashiach comes, clouds will come to take all the Jews to the Land of Israel. What does that mean for us? What is the meaning of those clouds?
A: There are two possibilities: If we merit, Mashaich will come on the clouds of heaven. If not, he will come on a donkey, “a poor person, riding on a donkey.” It depends upon us. The nation takes precedence over the king, so the manner in which the king is revealed depends upon the merit of the nation. Depending on the manner in which Mashiach comes, so will we ascend to the Land of Israel. (All the Jews throughout the world).
Mashiach is the miracle, but we don’t know what type of miracle will take place. Will it be a miracle enclothed in natural circumstances (Mashiach coming on a donkey) or a revealed, supernatural miracle (Mashiach coming on clouds)?
This is also the relationship between Pesach and Purim. On Pesach, the miracles were supernatural, while on Purim, the miracles were enclothed in natural circumstances.
If we merit, the miracles manifest miraculously, and the process goes more quickly. On clouds, everything goes quickly. If not, the process goes slowly, like a donkey. Mashiach enters the physical world and progresses with his tools, slowly.
In truth, we have to connect these two aspects together. After all, the very essence of Mashiach and the days of Mashiach is the ability to bear paradox. This is beautifully expressed in gematriah: ענן חמור = משיח בן דוד (Cloud donkey = Mashiach Ben David).