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Because these power struggles are seen through the lens of Israel, they are described in geographical reference to Israel. Thus, Seleucus who is located north of Israel is "the king of the North" while Ptolemy is "the king of the South."
Daniel 11:5
The king of the south will be strong, but one of his princes will be even stronger and will have great authority and power over his own kingdom.
Ptolemy reigned Egypt from 323-285BC. However, his successor Ptolemy II Philadelphus (285-245BC) became an even stronger king, establishing the great Library of Alexandria and commissioning the Septuagint translation of the Hebrew Scriptures into Greek -- the common trade language of the day.
Ptolemy 1 captured Jerusalem on a Sabbath day in 321BC without resistance, but in 316 lost Israel to his rival Antigonus. After the battle of Baza in 312BC, Ptolemy regained the territory with assistance from Seleucus Nicator (312-281BC). Seleucus established the Seleucid empire, ruling from Babylon.
Daniel 11:6
At the end of many years they will join together as allies. The daughter of the king of the south will come to the king of the north to make an agreement, but she will not retain her power and neither will he nor his power stand. At this time she will be handed over, together with the escorts that brought her and her father and the one who supported her.
A political marriage was arranged between Antiochus II Theos (262-246BC) and Ptolemy II Philadelphus' daughter Bernice. Antiochus had to divorce his wife Laodiceia, which enraged her. She responded by poisoning Antiochus and Bernice, along with their infant son and setting her elder son Seleucus II Callinicus on the throne (246-226BC). Note that his happened after the Septuagint translation that already included the complete book of Daniel along with this account.
Daniel 11:7
But out of her family line will arise one in his estate. He will come with an army, and will enter the fortress of the king of the north. He will fight against them, and will succeed.
The brother of the murdered Bernice, Ptolemy II Euergetes (245-221BC) sought revenge. He invaded Syria, seized the port of Antioch and overran Seleucus' empire all the way to Babylon.
Daniel 11:8
He will also seize and carry captive into Egypt their gods with molten images and their valuable articles of silver and gold. For certain years he will stay away from the king of the north.
Ptolemy II took huge spoils back to Egypt. These included 400 talents of gold, 40,000 talents of silver and 2,500 idols.
Daniel 11:9
Then the king [of the north] will invade the kingdom of the king of the south, but will retreat into his own land.
After two years Seleucus reorganized and marched south against Egypt, but was soundly defeated and returned to Antioch with only a small force remaining.
Note that your Bible may contain a remarkably different turn of events. There's a good reason for the confusion: the sentence structure in the Hebrew isn't very specific, making it quite easy to misunderstand. As a result, some Bibles such as the KJV appear to indicate that the king of the south attacks north, while others say that the king of the north invades southward, which is the intended meaning. The exact Hebrew reading goes something like this (Hebrew words in gold): bow [will invade] [the other] melek [kingdom] negeb [south] [and will] shuwb [turn away from, retreat] [to his own] adamah [land]. It's not hard to see why Bible translators could have gotten it wrong.
Daniel 11:10
But his sons will prepare for war, and will assemble a great army, one that will come and sweep through like a flood. Then he will return, and be stirred up all the way to his fortress.
Seleucus' sons were Seleucus III Ceraunus (226-223BC) who was murdered in Asia Minor, and Antiochus II, also known as Antiochus The Great. History books tend to have lots to say about Antiochus the Great (223-187BC) who recovered the fortress of Seleucia along with Tyre, then resumed the war with Egypt.
Daniel 11:11
Then the king of the south will be moved with rage, and will come and fight against the king of the north, who will raise a large army, but it will be defeated.
The army of Ptolemy IV Philopator (221-203BC) marched against Antiochus III. At the battle of Raphia just south of Gaza, Antiochus was defeated despite his larger army and signed a peace treaty with Ptolemy who then went on a tour of the Holy lands, though he was badly treated in Jerusalem. Curiously, while attempting to enter the Holy of Holies he was struck with a sudden unexplained paralysis and unable to enter.
Daniel 11:12
And when he has carried off the army, the king of the south will be filled with pride and will slaughter many tens of thousands, but he will not be strengthened by it.
Filled with pride and angry about what happened to him in Jerusalem, Ptolemy IV took out his humiliation when he returned to Egypt by murdering thousands of Egyptian Jews.
Daniel 11:13
For the king of the north will return with an even larger army than the previous one. After a few years he will advance with a huge army fully equipped.
After Ptolemy IV died, his four-year-old son succeeded him as Ptolemy V Epiphanes (203-181BC). Some 12 years after his defeat at the Battle of Raphia, Antiochus III set out with a greater army in an attempt to conquer Egypt.
Daniel 11:14
And in those times many will stand up against the king of the south. Violent criminals among your people will raise themselves up to fulfill the vision, but they will not succeed.
Antiochus had an ally in Philip of Macedon, the father of Alexander the Great. In addition, many vassal kings of Egypt opposed Ptolemy V.
In 200BC, an Egyptian Jew named Scopas raised up an army of mercenaries and rebels in an attempt to win Judea from Antiochus but he was defeated by Antiochus III's 100,000-strong army at Sidon in 198BC.
Daniel 11:15-16
Then the king of the north will come and build up seige ramps and capture the most fortified cities. The forces of the south will not withstand, not even their best troops, no one will have any strength to resist.
But the invader will do as he pleases, and none will be able to stand against him. He will set himself up in the glorious land, and will have the power to destroy it.
In the city that would later be named Caesarea Philippi north of Galilee, Antiochus took control of Palestine from the Egyptians for the last time, soundly defeating them at the Battle of Panion. Meanwhile the Romans were getting a foothold in Greece and working on their naval strength.
Daniel 11:17
He will be determined to enter with the might of his whole kingdom, so this is what he will do: he will give him his daughter in marriage to overthrow the kingdom. But she will not not remain loyal to helping him.
Increasing Roman control was beginning to play a role in the conflicts between the Seleucid and Egyptian empires. A peace accord was established in 196BC, which would later be utilized by Antiochus IV when he wrested control of the empire. Anticipating he would need to neutralize Egypt, Antiochus III had entered a marriage alliance, sending his daughter Cleopatra to be the bride of Ptolemy V. Because the boy was much too young at the time, the marriage wasn't consummated for several years. Antiochus expected her to be a useful spy, but instead she became loyal to her husband and his plans failed to help him.
Daniel 11:18-19
After this will he turn his attention toward the coastlands, and will take many of them. But a prince for his own behalf will put an end to his insolence and will cause it to turn back upon him.
Then he will turn his attention toward the fortresses of his own land, but he will stumble and fall, and will be seen no more.
In 192BC, Antiochus made his move towards Greece but was soundly defeated a year later at the Battle of Thermopylae. He then resorted to a sea battle to keep the Romans out of his territory, but was again defeated. He called for 70,000 reinforcements. Roman troops under Scipio were half that strength when they met at Magnesia about 50 miles north of Ephesus. But the Roman's superior military training and tactics so badly defeated Antiochus that he was completely wiped out in a humiliating defeat that led to a complete and total surrender. He had to pay a tribute equivalent to 30 million dollars. He was ruined.
Daniel 11:20
Then will arise a successor who will send a tax collector to maintain the glory of the kingdom. Within a few years he will be destroyed, but not in anger nor in battle.
Seleucus IV Philopator (187-175BC), a son of Antiochus III sent his treasurer Heliodorus to Jerusalem to seize funds in an effort to rebuild the coffers of an empire financially wiped out by war. He oppressed Israel through taxation. After 12 years Seleucus was murdered by Heliodorus who hoped to take over.
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