GL, here I prefer a christological explanation of the material. Dan. 11:22 mentions the "Leader of the covenant" which I believe to be the Christ (cf. Dan. 9:26, 27).
Exactor (of Taxes) (Dan. 11:20)
And there must stand up in his position one who is causing an exactor to pass through the splendid kingdom, and in a few days he will be broken, but not in anger nor in warfare.
???????? : Verb Qal Participle, one who is collecting taxes = a tax collector Dan. 11:20 (HALOT).
?????? : Verb Qal Perfect, an exactor of tribute (BDBLex). To collect (offerings) 2 Kings 23:35. [“ And the silver and the gold Jehoiakim gave to Pharaoh. Only he taxed the land, to give the silver at the order of Pharaoh. According to each one's individual tax rate he exacted the silver and the gold from the people of the land, to give it to Pharaoh Nechoh.”]
In the book of Daniel “stand up” often refers to a king starting his reign (cf. Dan. 8:23; 11:3, 7, 20, 21; 12:1). In A Commentary on the Book of Daniel by John J. Collins, pp. 381, 382, we read: 20.In his place will arise one: Seleucus IV Philopator (187-175 B.C.E.). His reign was dominated by financial exigency, because of the tribute to Rome.
who will make a tribute collector of royal splendor pass through : This is most probably a reference to Heliodorus, whose attempt to despoil the Jerusalem Temple is recounted in 2 Maccabees 3.
in some days he will be broken : Seleucus reigned for twelve years, but his reign is dismissed as short and inconsequential. He fell victim to a plot by Heliodorus, hence the emphasis on the secrecy of his death.
21. In his place will arise a contemptible man: The contemptible man is Antiochus IV Epiphanes, who is consistently derided in Daniel, etc.
Keil & Delitzsch found it hard to place the verse in such a historical setting. They gave the following reasons for their misgivings: “Finally, of his successor, Seleucus Philopator, to whom v. 20 must refer, if the foregoing verses treat of Antiochus the Great, nothing further is communicated, than that he quum paternis cladibus fractas admodum Syriae opes accepisset, post otiosum nullisque admodum rebus gestis nobilitatum annorum duodecim regnum, was put to death through the treachery of Heliodorus, unius ex purpuratis (Liv. xli. 19, cf. App. Syr. c. 45), and the mission of Heliodorus to Jerusalem to seize the treasures of the temple, which is fabulously described in 2 Macc. 3:4ff. The ????????? (shall be destroyed) of this king ????????? ???????? (within few days) does not harmonize with the fact of his twelve years’ reign.
Thus, Dan. 11:20, mentions an exactor (of taxes, cf. 2 Kings 23:35) that will pass through the splendid kingdom, taking the place of the King of the North. As an alternative interpretation, we look to Caesar Augustus, enrolling the people. During this time Jesus would be born in Bethlehem (cf. Luk. 2:1-5).
Above explanation is in harmony with the facts. The Roman Empire would flourish under the reign of Caesar Augustus. He would order the registration of “all the inhabited earth” for tax purposes as well as military conscription (cf. Luke 2:1). Augustus will then be broken, “but not in anger nor in warfare”. He would die of illness. His successor, “one to be despised”, would take over the kingdom “by means of smoothness” (cf. Dan. 11:20, 21).
“Tiberius,” says TheNewEncyclopædiaBritannica, “played politics with the Senate and did not allow it to name him emperor for almost a month [after Augustus died].” He told the Senate that no one but Augustus was capable of carrying the burden of ruling the Roman Empire and asked the senators to restore the republic by entrusting such authority to a group of men rather than to one man.
“Not daring to take him at his word,” wrote historian Will Durant, “the Senate exchanged bows with him until at last he accepted power.” Durant added: “The play was well acted on both sides. Tiberius wanted the principate, or he would have found some way to evade it; the Senate feared and hated him, but shrank from re-establishing a republic based, like the old, upon theoretically sovereign assemblies.” Thus, in a crafty way Tiberius would take hold of the Roman Empire by means of smoothness .