What does Daniel 11:16 mean?

When Daniel first received these prophecies, it was 536 BC (Daniel 10:1). What the angel tells him (Daniel 10:18–21; 11:2) is reasonably literal, referring to battles, nations, and kings using generic terms (Daniel 11:10–14). Centuries later, these predictions would be fulfilled; using the hindsight of history, we can put precise names and faces to biblical prophecy including the back-and-forth exchange of Israelite territory over the course of wars between Syria and Egypt (Daniel 11:10–14). The prior verse noted the defeat of "the forces of the south," who were overcome after the "king of the north" returned with a larger army and more allies. This corresponds to Antiochus III, who captured the city of Sidon and established firm Syrian control over the region, rendering Egypt irrelevant.

Eventually, Antiochus turned his attention to other concerns. His dominance in the Israel-Syria region was uncontested. Yet the Roman Empire, to the west, was beginning to pose a threat. Worse, Rome had friendly relations with Egypt and its grain exporters. Antiochus married his daughter to the Egyptian king. This only delayed renewed war between the two nations (Daniel 11:17).

Some Israelites had fought with Antiochus III, likely hoping to earn independence. Instead, Antiochus subjugated the Jews so they would never serve Egypt again. However, the Jewish people did not hate him. According to Josephus the historian, Antiochus granted favors to the Jews in Israel as compensation for the injuries they had suffered in the wars that had been fought in Israel between Antiochus and Egypt's generals (Josephus, Ant. B. XII.ch, iii). When Antiochus defeated Egypt, the Jews sided with Antiochus and welcomed him into Jerusalem.

Unfortunately, one of Antiochus III's sons and successors was Mithradates, later known as Antiochus IV Epiphanes: one of Israel's most infamous and hated persecutors (Daniel 8:23–25).