The first Jew to dream about Alexander the Great was Daniel, a eunuch slave in Babylon. This was a vision at the River Shushan in the land of Elam.
Daniel 8:5-8 “And as I was considering, behold, an he goat came from the west on the face of the whole earth, and touched not the ground: and the goat [had] a notable horn between his eyes. And he came to the ram that had [two] horns, which I had seen standing before the river, and ran unto him in the fury of his power. And I saw him come close unto the ram, and he was moved with choler against him, and smote the ram, and brake his two horns: and there was no power in the ram to stand before him, but he cast him down to the ground, and stamped upon him: and there was none that could deliver the ram out of his hand. Therefore the he goat waxed very great: and when he was strong, the great horn was broken; and for it came up four notable ones toward the four winds of heaven.”
The “he goat” is Alexander the Great. Alexander destroyed Persia, the “ram”. The great horn was Alexander’s Empire. The four “notable” horns that came up afterward were the four regions into which that empire was divided after the death of Alexander.
The second Jew to dream about Alexander was Rabbi Jaddua. According to the Jewish historian Josephus, Rabbi Jaddua saw a dream in which he wore his priestly robes and took his official head priest staff and went to see Alexander.
Rabbi Jaddua understood the dream was from Jehovah, and did as he saw in the dream. When Alexander saw the rabbi, he dismounted his horse and bowed to him. (Some accounts say he fell prostrate on the ground.) This was very rare for Alexander to bow to anyone. Parmerio, Alexander’s top general asked about the bow. To this, Alexander answered that he had seen the man in a dream and understood that the God of this man was the one who gave him victory. So, he had bowed to the god of the rabbi (Jehovah), and not to Rabbi Jaddua himself. Some accounts say that Alexander saw this rabbi, attired in royal robes, go before him in every battle.
Alexander the Great went to the Temple of the Lord in Jerusalem and worshiped Almighty God. The rabbis showed him the text of Daniel chapter 8. To this, Alexander rejoiced and he believed (correctly) that he would fulfill the vision.