(v. 5)Then the king of the South [Ptolemy I] will grow strong, along with one of his princes [Seleucus I] who will gain ascendancy over him and obtain dominion; his domain will be a great dominion indeed.

The king of the South is a reference to Ptolemy I Soter (ruled 323-282 BC). Alexander himself had come to Egypt in 332 BC, at which time the country quickly surrendered to him. After Alexander’s death, his military commanders fought one another (the Wars of the Diadochi) for 22 years until a peace settlement was attained in 301 BC. Ptolemy I gained control of the highly prized Egypt. However there was a dispute as to who had control of the territories of Judah, Phoenicia and lower Syria (collectively known as Coele-Syria). Ptolemy I had laid claim to them as early as 318 BC. Seleucus I initially served as governor of Babylon. But he was forced to flee Babylon on account of the aggressions of Antigonus, another Macedonian general under Alexander. Seleucus I then sought protection and refuge with Ptolemy I, and the two entered into league with one another. In this sense, Seleucus I was one of Ptolemy’s princes (Heb שריו ). The inter-fighting between the Diadochi was finally settled in 301 BC as a result of the Battle of Ipsus (in Phrygia of Asia Minor). In this battle Antigonus and those allied with him were defeated, and Seleucus I (one of the victors) received the bulk of Antigonus' holdings: eastern Asia Minor and certain lands in the east (including Babylonia and northern Syria). At this point Seleucus had the largest portion of what had been Alexander’s empire, and thus a great dominion. Seleucus I moved his capital from a location in Babylonia (Seleucia-on-the-Tigris) to Antioch in northern Syria. He also claimed Coele-Syria, which brought him into conflict with Ptolemy I (with whom he had previously been allied). Although there was a temporary resolve of this conflict, it failed to produce a firm agreement as to who had the rightful ownership of Coele-Syria (which included the biblical lands of Judea). This then, became the origin of the Syrian Wars between the Ptolemaic and Seleucid kings. Ptolemy I died in 282 BC and Seleucus I just one year later in 281 BC.

(v. 6) After some years they will form an alliance, and the daughter of the king of the South [Berenice] will come to the king of the North [Antiochus II] to carry out a peaceful arrangement.

In v. 6, "they" refers to the Ptolemaic and Seleucid rulers. The conflict between Ptolemy I and Seleucus I continued on with their sons and led to the First Syrian War (274-271 BC), initiated by Ptolemy II Philadelphus against the son and successor of Seleucus I, Antiochus I Soter (ruled 281-261 BC). Initially Ptolemy II launched "a military campaign against Seleucid Syria, but had to treat in the face of an advance by Antiochus I who mobilized new units in Babylon" (Holbl, 40). Yet Antiochus I had to call off his plans, and Damascus remained a Ptolemaic stronghold. A new Seleucid king came to the throne in 261 BC, namely, Antiochus II (ruled 261-246 BC). Hostilities quickly flared again that led to the Second Syrian War (260-253 BC). A peaceful arrangement between the two kingdoms was finally concluded by 253 BC, strengthened by a marriage alliance in 252 BC. The daughter of the king of the South refers to Berenice, the daughter of Ptolemy II Philadelphus (ruled 282-246 BC) and his first wife Arsinoe I of Egypt. Berenice (also called Berenice Syra) was given as a wife to the king of the North, Antiochus II, though the latter already had a wife named Laodice I. Nevertheless Antiochus II repudiated his first wife Laodice I and exiled her to Ephesus (following an agreement with Ptolemy II), and then transferred the right of succession to Berenice’s children.

But she [Berenice] will not retain her position of power, nor will he [Antiochus II] remain with his power, but she will be given up, along with those who brought her in and the one who sired her as well as he who supported her in those times.

In 246 BC, when Ptolemy II died, Antiochus II took up again with his first wife, Laodice. The Syrian king died shortly afterwards (also in 246 BC), many suspect from poisoning by Laodice. Laodice, the former queen, asserted that Antiochus II on his deathbed had proclaimed that one of her sons, Seleucus II, would be the new king. Yet Queen Berenice claimed the Regency for her infant son (also named Antiochus) and tried to organize an army behind her. However at Laodice’s wishes, Berenice and her son were both killed, thereby ending her position of power.

[Note: the translation "the one who sired her" reflects the vowel pointing of the Masoretic Hebrew text for הילדה , but the NET Bible opts for the translation "her child," based on an alternative pointing of the text (and supported by Theodotion, the Syriac, and the Latin Vulgate). The definite article ה on the front of the word, however, argues against the reading "her child"].

(v. 7) But one of the descendants of her line [Ptolemy III] will arise in his place, and he will come against their army and enter the fortress of the king of the North [Seleucus II], and he will deal with them and display great strength.

Laodice’s son, Seleucus II Callinicus, did become the new Seleucid king of the North (ruled 246-226 BC). Yet the atrocities against Berenice (and thus against Ptolemaic Egypt) inaugurated the Third Syrian War (246-241 BC). Berenice's brother, Ptolemy III Euergetes (r. 246-221 BC)—a descendant of her line—succeeded their father and set about to avenge his sister's murder by invading Syria, attacking the Seleucid army, and having Laodice killed. Ptolemy III even entered the Seleucid fortress at Antioch, which was still controlled by those loyal to Berenice. In his great strength, Ptolemy III went on to lead a very successful campaign against Syria, and even marched all the way to Mesopotamia.

(v. 8) Also their gods with their metal images and their precious vessels of silver and gold he [Ptolemy III] will take into captivity to Egypt, and he on his part will refrain from attacking the king of the North [Seleucus II] for some years.

In his triumphant campaign through the Seleucid Empire, Ptolemy III plundered and pillaged numerous objects of value, taking back a great treasure to Egypt. Yet an uprising of local Egyptians in early 245 BC caused him to suddenly return to Egypt, which allowed Seleucus II to assert himself and gain control over the Seleucid Empire. In exchange for peace in 241 BC (which concluded the Third Syrian War), Ptolemy III was awarded new territories on the northern coast of Syria, including Seleucia Pieria on the Orontes River, the port city of Antioch. The Ptolemaic kingdom reached the height of its power under Ptolemy III, and following the Third Syrian War he ruled successfully for another 20 years until his death in 221 BC.

(v. 9) Then the latter [Seleucus II] will enter the realm of the king of the South, but will return to his own land.

The event referred to in v. 9 is not clear, but may relate to a minor conflict near Damascus toward the end of the Third Syrian War (ca. 242/41 BC). The Roman historian Justin even records that Seleucus II attempted an attack on Egypt about this time. Nevertheless, Seleucus II was beset with political and military troubles in various parts of his realm, which prevented him from being able to wage war with Egypt during the rest of his reign.

(v. 10) His sons [Seleucus III and Antiochus III] will mobilize and assemble a multitude of great forces; and one of them [Antiochus III] will keep on coming and overflow and pass through, that he may again wage war up to his very fortress.

Seleucus II died in 226 BC. Among his several children were his sons Seleucus III Soter (also called Seleucus Ceraunus) and Antiochus III the Great (born near Susa in Persia). The elder son, Seleucus III reigned initially in the place of his father (226-222 BC), but he was assassinated in Anatolia by members of his army while on campaign against Attalus I of Pergamon. As a result, Antiochus III became the next Seleucid king (ruled 222-187 BC) at the mere age of eighteen. Not long after Antiochus III became king, Ptolemy III died (221 BC) and was replaced by his son, Ptolemy IV Philopator (ruled 221-204 BC). Ptolemy IV was a weak ruler, and under him the Ptolemaic kingdom began to decline. Antiochus III saw in this an opportunity to expand his own kingdom. In 221 BC he attempted an assault upon the Ptolemaic forces that occupied strongholds in the Beqaa Valley of Phoenicia (present-day Lebanon). But he was unsuccessful and had to withdraw. Shortly thereafter he was side-tracked by uprisings in his own kingdom in the territories of Media and Persis (present-day Iran). By 219 BC, Antiochus III was ready to resume his attack against the northern Ptolemaic frontier, and he seized the naval stronghold of Seleucis Pieria (a port city near Antioch). This act initiated the Fourth Syrian War (219-217 BC). He was aided in this by a Ptolemaic general named Theodotos of Aetolia, who betrayed the Egyptians and helped deliver Coele-Syria to Antiochus III. This enabled Antiochus III to quickly take control of Tyre and Ptolemais (and also gaining 40 ships in the process).

(v. 11) The king of the South [Ptolemy IV] will be enraged and go forth and fight with the king of the North [Antiochus III]. Then the latter will raise a great multitude, but that multitude will be given into the hand of the former.

(v. 12) When the multitude is carried away, his heart [Ptolemy IV] will be lifted up, and he will cause tens of thousands to fall; yet he will not prevail.

In 217 BC, however, Ptolemy IV made a counter-attack against Antiochus III at the Battle of Raphia (SW of present-day Gaza). Thousands of infantry, cavalry, and war elephants were involved in the battle. Antiochus’s army was indeed a great multitude, for along with his regular forces he was joined by 10,000 Nabataeans and other Arab tribes. Yet in the end Ptolemy IV prevailed and won the Battle of Raphia. As a result, Ptolemy IV regained the important territory of Coele-Syria, while Antiochus (responsible for the death of thousands) retreated to Antioch. The great Egyptian victory of Raphia in 217 BC secured the northern borders of the Ptolemaic kingdom for the remainder of the reign of Ptolemy IV. Antiochus III spent the next 13 years of his rule putting down revolts in his own kingdom, and in this was quite successful. "He also assumed the title 'Basileus Megas' (which is Greek for 'Great King'), the traditional title of the Persian kings" (Wiki: Antiochus III).

(v. 13) For the king of the North [Antiochus III] will again raise a greater multitude than the former, and after an interval of some years he will press on with a great army and much equipment.

(v. 14) Now in those times many will rise up against the king of the South [Ptolemy V]; the violent ones among your people [Jewish revolutionaries] will also lift themselves up in order to fulfill the vision, but they will fall down.

An interval of some years went by. But when Ptolemy IV died in 204 BC, Antiochus III saw his opportunity to finally strike back at Egypt. The new Egyptian king, Ptolemy V Epiphanes (ruled 204-180 BC), was but six years of age, and there was much turmoil in Alexandria due to fighting over the regency. Antiochus III, armed with a great army and much equipment, is said to have made a secret pact with Philip V of Macedon for the partition of the Ptolemaic empire. Then, early in 202 BC, Antiochus III began what has become known as the Fifth Syrian War (202-ca. 195 BC) by attacking Damascus. Assisting Antiochus was a number of pro-Seleucid Jewish revolutionaries—violent ones among Daniel’s people—who were discontent with Egypt’s rule over Judea. Once more Antiochus III attacked the Ptolemaic province of Coele-Syria and Phoenicia (aided by the defection of a Ptolemaic governor), though the coastal cities of Phoenicia remained in the hands of Ptolemaic rule. Antiochus III was initially successful, until Skopas, an Aetolian (Greek) general whom Ptolemy V had given command of Coele-Syria, recovered it for Ptolemy. That recovery, however, was to prove brief.

(v. 15) Then the king of the North [Antiochus III] will come, cast up a siege ramp and capture a well-fortified city; and the forces of the South [Egyptians] will not stand their ground, not even their choicest troops, for there will be no strength to make a stand.

(v. 16) But he who comes against him will as he pleases [i.e., Antiochus III], and no one will be able to withstand him; he will also stay for a time in the Beautiful Land [Judea], with destruction in his hand.

In 200 BC Antiochus launched a second offensive, and this time defeated the Ptolemaic general Skopas at the Battle of Panium, near the sources of the Jordan River. One significant outcome of this battle is that it marked the end of Ptolemaic rule in Judea. This forced Skopas to retreat with 10,000 men to the well-fortified coastal city of Sidon in Phoenicia (a Ptolemaic stronghold). Antiochus III pursued him there and cast up siege mounds against the fortress walls. Shutting himself up within the walls of Sidon, after an ineffectual attempt by Ptolemy to relieve him Skopas was ultimately compelled by famine to surrender in 199 BC to Antiochus III (Polybius XIII.1-2, XVI.18-19, 39; Josephus, Antiquities XII.3.3). The important port-city of Sidon had now fallen to Seleucid control, an event that enabled the Seleucids to maintain control over the interior lands. Since Egypt was too weak to mount another offensive, Antiochus III could essentially as he pleased. Antiochus III (with power to destroy) spent the first half of 198 BC extending his control over the rest of the former province of Coele-Syria, including Judea and Jerusalem, the Beautiful Land. Antiochus now completely dominated Coele-Syria, the prize that the Seleucid kings had long sought for (and felt was their rightful possession) since the Battle of Ipsus in 301 BC.

(v. 17) He [Antiochus III] will set his face to come with the power of his whole kingdom, bringing with him a proposal of peace which he will put into effect; he [Antiochus III] will also give him [Ptolemy V] the daughter of women [Cleopatra I] to ruin it. But she will not take a stand for him [Antiochus III] or be on his side.

Rather than directly attacking Egypt, Antiochus III used the time to extend his power in Asia Minor, initiating a great campaign there in 197 BC in which a number of previously Ptolemaic cities came under Seleucid control. The capstone to this was Antiochus' conquest of Ephesus in the autumn of 197 BC, which had been a powerful and well-garrisoned Ptolemaic base. By the close of 197 BC, the Alexandrian government had lodged its complaints in Rome against Antiochus's conquests (especially in Asia Minor), and the Roman senate sent a man of consular rank, L. Cornelius Lentulus, to help resolve the tensions. With this, Rome was clearly extending its influence into the eastern Mediterranean (which would lead in the course of time to her conquest of all these territories). In 196 BC, Rome attempted to exert pressure on Antiochus to come to peace with Ptolemaic Egypt and return the captured territories. This prompted Antiochus to make a diplomatic maneuver of proposing peace with Egypt, sealing it by means of a political marriage. In the winter of 194/93 BC, Antiochus's daughter Cleopatra I (though only about 10 years old) was wed to the 16 year-old Egyptian king, Ptolemy V. Yet Antiochus did this with treachery in mind: he would give the king of the South a daughter in marriage in order to destroy the kingdom (11:17). In the ensuing years, however, this hoped-for tactic did not turn out to his advantage.

(v. 18) Then he [Antiochus III] will turn his face to the coastlands and capture many. But a commander [a Roman general] will put a stop to his scorn against him; moreover, he will repay him for his scorn.

Following "peace" with Egypt through the marriage alliance involving his daughter Cleopatra I, Antiochus III turned his attention to the coastal regions of Asia Minor where he captured many of them. This, however, brought him into further conflict with the Romans. In 192 BC, Antiochus III invaded Greece with a 10,000 man army, and was even elected the commander in chief of the Aetolians (who were fighting Rome at that time). Yet the Romans prevailed over Antiochus III. In 191 BC, the Romans under the command of Manius Acilius Glabrio routed Antiochus III at Thermopylae, forcing him to withdraw to Asia. Then in 190 BC, a decisive Roman victory was achieved by Scipio Asiaticus at the Battle of Magnesia (eastern province of central Greece), thereby giving Asia Minor into Roman hands. This is the Roman commander that put a stop to Antiochus III. The latter was made to pay for his shameful conduct by signing the Treaty of Apameia in 188 BC, thereby abandoning all the country

(v. 19) So he [Antiochus III] will turn his face toward the fortresses of his own land, but he will stumble and fall and be found no more.

The Treaty of Apameia had two important results for Seleucid history (and one which was to significantly affect Judea). First, the treaty called for the taking of 20 hostages to Rome, and one of these turned out to be the son of Antiochus III, Mithridates (later renamed Antiochus IV Ephiphanes), the famous persecutor of the Jews. Second, the treaty resulted in a growing assertion of independence by the outlying provinces of the empire, which prompted Antiochus III to make yet another expedition to the eastern provinces of his own land. He came to Elymaïs, close to the ancient Persian capital of Susa, but more recently having come under Parthian control. There in the middle of 187 BC, Antiochus "fell"—he and his soldiers were killed while plundering the temple of Bel by the outraged inhabitants of the area.

(v. 20) Then in his place one will arise [Seleucus IV] who will send an oppressor through the Jewel of his kingdom;

Next in line to Antiochus III was his son, Seleucus IV Philopator (ruled 187-175 BC). On the one hand, Seleucus IV had the advantage of a large kingdom, which included Syria, Cilicia, Judea, Mesopotamia, Babylonia, and Nearer Iran (Media and Persia). Yet on the other hand, Seleucus faced enormous financial challenges. Strapped with a heavy war-indemnity exacted by Rome, he was forced to secure more financial resources by heavy taxation. For this reason, Seleucus IV sent out an "oppressor," that is, one who went throughout his empire to collect tribute and taxes. Naturally this was very unpopular with his peoples. Around 178 BC, Seleucus IV sent one of his government officials named Heliodorus (the "oppressor") to Jerusalem of Judea (the Jewel of his kingdom) to confiscate the money and treasures in the Jewish Temple (cf. 2 Macc 3:1-40).

yet within a few days he [Seleucus IV] will be shattered, though not in anger nor in battle.

Seleucus IV did not die in battle. Rather he was assassinated ("shattered") by his own official, Heliodorus, when the latter returned from his trip to Jerusalem. Heliodorus then attempted to seize the throne for himself.

(v. 21) In his place a despicable person [Antiochus IV] will arise, on whom the honor of kingship was not been conferred, but he will come in a time of tranquility and seize the kingdom by intrigue.

The most despicable person of all the Seleucid rulers was clearly Antiochus IV Epiphanes (ruled 175-164 BC), on account of his brutal persecution of the Jewish people. The books of I and II Maccabees were written to tell the story of his oppression and how the Jewish people rose up to overthrow him.

Antiochus IV was a younger brother of Seleucus IV (both being sons of Antiochus III), but he was not the next in line to the throne. The true heir to the throne was Seleucus’s own son, Demetrius I Soter, but he was only ten years old and was still retained in Rome as a hostage. Antiochus IV took advantage of Demetrius’s absence by having Heliodorus murdered and seizing the throne for himself (with the help of King Eumenes II of Pergamum). Initially Antiochus IV was able to get away with this by proclaiming himself co-regent with another son of Seleucus IV (also named Antiochus), but then later had him murdered. Thus the honor of kingship had not been rightfully conferred upon him. Rather Antiochus IV had seized the kingdom by intrigue.