Genesis 49 – Skeptic's Annotated Bible answered

1 And Jacob called unto his sons, and said, Gather yourselves together, that I may tell you that which shall befall you in the last days.

2 Gather yourselves together, and hear, ye sons of Jacob; and hearken unto Israel your father.

3 Reuben, thou art my firstborn, my might, and the beginning of my strength, the excellency of dignity, and the excellency of power:

4 Unstable as water, thou shalt not excel; because thou wentest up to thy father’s bed; then defiledst thou it: he went up to my couch.

(49:4) "Thou wentest up to thy father's bed."
Jacob says that Reuben will "not excel" because he "went up to [his] father's couch [had sex with his father's wife]." (see Genesis 35:22)

5 Simeon and Levi are brethren; instruments of cruelty are in their habitations.

6 O my soul, come not thou into their secret; unto their assembly, mine honour, be not thou united: for in their anger they slew a man, and in their selfwill they digged down a wall.

7 Cursed be their anger, for it was fierce; and their wrath, for it was cruel: I will divide them in Jacob, and scatter them in Israel.

8 Judah, thou art he whom thy brethren shall praise: thy hand shall be in the neck of thine enemies; thy father’s children shall bow down before thee.

9 Judah is a lion’s whelp: from the prey, my son, thou art gone up: he stooped down, he couched as a lion, and as an old lion; who shall rouse him up?

10 The sceptre shall not depart from Judah, nor a lawgiver from between his feet, until Shiloh come; and unto him shall the gathering of the people be.

(49:10) "Until Shiloh come"
The tribe of Judah will reign "until Shiloh," but Israel's first king (Saul) was from the tribe of Benjamin (Acts 13:21), and most of the time after this prophecy there was no king at all.

11 Binding his foal unto the vine, and his ass’s colt unto the choice vine; he washed his garments in wine, and his clothes in the blood of grapes:

(49:11) "He washed his garments in wine ... His eyes shall be red with wine."
Did Judah really wash his clothes in wine? Were his eyes bloodshot from drinking too much? Or is this a prophecy of Jesus? (I didn't know Jesus had a drinking problem.)

12 His eyes shall be red with wine, and his teeth white with milk.

13 Zebulun shall dwell at the haven of the sea; and he shall be for an haven of ships; and his border shall be unto Zidon.

14 Issachar is a strong ass couching down between two burdens:

15 And he saw that rest was good, and the land that it was pleasant; and bowed his shoulder to bear, and became a servant unto tribute.

16 Dan shall judge his people, as one of the tribes of Israel.

17 Dan shall be a serpent by the way, an adder in the path, that biteth the horse heels, so that his rider shall fall backward.

18 I have waited for thy salvation, O LORD.

19 Gad, a troop shall overcome him: but he shall overcome at the last.

20 Out of Asher his bread shall be fat, and he shall yield royal dainties.

21 Naphtali is a hind let loose: he giveth goodly words.

22 Joseph is a fruitful bough, even a fruitful bough by a well; whose branches run over the wall:

23 The archers have sorely grieved him, and shot at him, and hated him:

24 But his bow abode in strength, and the arms of his hands were made strong by the hands of the mighty God of Jacob; (from thence is the shepherd, the stone of Israel:)

25 Even by the God of thy father, who shall help thee; and by the Almighty, who shall bless thee with blessings of heaven above, blessings of the deep that lieth under, blessings of the breasts, and of the womb:

26 The blessings of thy father have prevailed above the blessings of my progenitors unto the utmost bound of the everlasting hills: they shall be on the head of Joseph, and on the crown of the head of him that was separate from his brethren.

27 Benjamin shall ravin as a wolf: in the morning he shall devour the prey, and at night he shall divide the spoil.

28 All these are the twelve tribes of Israel: and this is it that their father spake unto them, and blessed them; every one according to his blessing he blessed them.

29 And he charged them, and said unto them, I am to be gathered unto my people: bury me with my fathers in the cave that is in the field of Ephron the Hittite,

30 In the cave that is in the field of Machpelah, which is before Mamre, in the land of Canaan, which Abraham bought with the field of Ephron the Hittite for a possession of a buryingplace.

31 There they buried Abraham and Sarah his wife; there they buried Isaac and Rebekah his wife; and there I buried Leah.

32 The purchase of the field and of the cave that is therein was from the children of Heth.

33 And when Jacob had made an end of commanding his sons, he gathered up his feet into the bed, and yielded up the ghost, and was gathered unto his people.