For the ships of Chittim shall come against him: therefore he shall be grieved, and return, and have indignation against the holy covenant: so shall he do; he shall even return, and have intelligence with them that forsake the holy covenant.
For the ships of Chittim shall come against him - the Roman ambassadors arriving in Macedonian-Grecian vessels (see note, Jeremiah 2:10). Chittim means properly Cyprians, so called from a Phoenician colony in Cyprus: then the term came to be applied to the islands and coasts of the Mediterranean in general.
Therefore he shall be grieved - he shall be humbled and dispirited through fear of Rome.
And return, and have indignation against the holy covenant - indignant that meantime God's worship has been restored at Jerusalem, he gives vent to his wrath at the check given him by Rome on the Jews.
He shall even return, and have intelligence with them that forsake the holy covenant - namely, with the apostates in the nation (1Ma 1:11-15). Menelaus and other Jews instigated the king against their religion and country. Having taken up the false idea from Greek philosophy, that the main object of religion is to maintain political and social order, and that all religions are good enough to keep the masses in check, these had cast off circumcision and the religion of Yahweh for Greek customs. Antiochus, on his way home sent Apollonius (167 BC) with 22,000 to destroy Jerusalem, two years after its capture by himself. Apollonius slew multitudes, and dismantled and pillaged the city. They then, from a fortress which they built, commanding the temple, fell on and killed the worshippers; so that the temple service was discontinued.
Also, Antiochus decreed that all, on pain of death, should conform to the Greek religion, and the temple was consecrated to Jupiter Olympius. Identifying himself with that god, with fanatical haughtiness, he wished to make his own worship universal (1Ma 1:41 , 'King Antiochus wrote to his whole kingdom that all should be one people, and every one should leave his laws: so all the pagan agreed ... Yea, many also of the Israelites consented to his religion, and sacrificed unto idols, and profaned the Sabbath;' 2Ma 6:7 , 'In the day of the king's birth, every month, they were brought by bitter constraint to eat of the sacrifices; and when the feast of Bacchus was kept, the Jews were compelled to go in procession to Bacchus, carrying ivy'). This was the gravest peril which ever heretofore threatened revealed religion, the holy people, and the theocracy on earth. For none of the previous world-rulers had interfered with the religious worship of the covenant-people when subject to them (Daniel 4:31-34; Daniel 6:27-28; Ezra 1:2; Ezra 1:4; Ezra 7:12; Nehemiah 2:18). Hence, arose the need of such a forewarning of the covenant-people as to him-so accurate, that Porphyry, the adversary of revelat ion, saw it was hopeless to deny its correspondence with history, but argued from its accuracy that it must have been written subsequent to the event. But as Messianic events are foretold in Daniel, the Jews, the adversaries of Jesus, would never have forged the prophecies which confirm His claims. The ninth chapter was to comfort the faithful Jews, in the midst of the 'abominations' against "the covenant," with the prospect of Messiah, who would confirm the covenant. He would show, by bringing salvation, and yet abolishing sacrifices, that the temple service, which they so grieved after, was not absolutely necessary: thus the correspondence of phraseology would suggest comfort (cf. Daniel 9:27 with Daniel 11:30-31).