Where is it called a sin offering in the text? Keep in mind that I would be asking for the specific Hebrew word, which I am pretty sure is not there.
Isa 53:10 Yet it pleased the LORD to bruise him; he hath put him to grief: when thou shalt make his soul an offering for sin, he shall see his seed, he shall prolong his days, and the pleasure of the LORD shall prosper in his hand.
The word here translated "sin offering":
Transliterated Word TDNT Entry
'asham TWOT - 180b
Phonetic Spelling Parts of Speech
aw-shawm' Noun Masculine
Definition
guilt, offense, guiltiness
offense, trespass, fault
guilt, guiltiness
compensation (for offense)
trespass offering, guilt offering
King James Word Usage - Total: 46
trespass offering 34, trespass 8, offering for sin 1, sin 2, guiltiness 1
'asham - Old Testament Hebrew Lexicon - King James Version
Same word used throughout here:
Leviticus 5:6-7; Leviticus 5:15-16; Leviticus 5:18-19; Leviticus 6:6; Leviticus 7:1-2; Leviticus 7:7; Leviticus 7:37; Leviticus 14:12-14; Leviticus 14:21; Leviticus 14:24-25; Leviticus 19:21-22 Ezekiel 42:13; Ezekiel 44:29; Ezekiel 46:20
Here is the Complete Jewish Bible translation:
Isaiah 53:10
Complete Jewish Bible (CJB)
10 yet it pleased Adonai to crush him with illness,
to see if he would present himself as a guilt offering.
If he does, he will see his offspring;
and he will prolong his days;
and at his hand Adonai’s desire
will be accomplished.
And Young's Literal Translation:
Isaiah 53:10
Young's Literal Translation (YLT)
10 And Jehovah hath delighted to bruise him, He hath made him sick, If his soul doth make an offering for guilt, He seeth seed -- he prolongeth days, And the pleasure of Jehovah in his hand doth prosper.
And the KJV
Isaiah 53:10
King James Version (KJV)
10 Yet it pleased the Lord to bruise him; he hath put him to grief: when thou shalt make his soul an offering for sin, he shall see his seed, he shall prolong his days, and the pleasure of the Lord shall prosper in his hand.
And here is the entire chapter again, highlighting the same sense of "bearing" guilt, this time in the Complete Jewish Bible:
Isaiah 53
Complete Jewish Bible (CJB)
53 Who believes our report?
To whom is the arm of Adonai revealed?
2 For before him he grew up like a young plant,
like a root out of dry ground.
He was not well-formed or especially handsome;
we saw him, but his appearance did not attract us.
3 People despised and avoided him,
a man of pains, well acquainted with illness.
Like someone from whom people turn their faces,
he was despised; we did not value him.
4 In fact,
it was our diseases he bore,
our pains from which he suffered;
yet we regarded him as punished,
stricken and afflicted by God.
5
But he was wounded because of our crimes,
crushed because of our sins;
the disciplining that makes us whole fell on him,
and by his bruises* we are healed.
6 We all, like sheep, went astray;
we turned, each one, to his own way;
yet Adonai laid on him
the guilt of all of us.
7 Though mistreated, he was submissive —
he did not open his mouth.
Like a lamb led to be slaughtered,
like a sheep silent before its shearers,
he did not open his mouth.
8 After forcible arrest and sentencing,
he was taken away;
and none of his generation protested
his being cut off from the land of the living
for the crimes of my people,
who deserved the punishment themselves.
9 He was given a grave among the wicked;
in his death he was with a rich man.
Although he had done no violence
and had said nothing deceptive,
10
yet it pleased Adonai to crush him with illness,
to see if he would present himself as a guilt offering.
If he does, he will see his offspring;
and he will prolong his days;
and at his hand Adonai’s desire
will be accomplished.
11 After this ordeal, he will see satisfaction.
“By his knowing [pain and sacrifice],
my righteous servant makes many righteous;
it is for their sins that he suffers.
12 Therefore I will assign him a share with the great,
he will divide the spoil with the mighty,
for having exposed himself to death
and being counted among the sinners,
while actually bearing the sin of many
and interceding for the offenders.”
As to the "he" thing, Israel is referred to collectively as a he in multiple places. To give you an example:
Hosea 11:1
When Israel was a child, I loved him, and out of Egypt I called my son.
This is obviously speaking about corporate Israel and him.
The difference between this sentence from Hosea, and these sentences from Isaiah:
Isa 53:5-6 But he was wounded for our transgressions, he was bruised for our iniquities: the chastisement of our peace was upon him; and with his stripes we are healed. (6) All we like sheep have gone astray; we have turned every one to his own way; and the LORD hath laid on him the iniquity of us all.
Is that in the first one, it is clear the subject is Israel, and it is clear he is being discussed. In the latter sentences, they are talking about one receiving wounds, and the other "us" being healed by them. So, how then does Israel, corporately, receive wounds, and Israel, individually among the people, receive the healing?
It is illogical, therefore.
The whole chapter (and forth servant song in general) occurs in the messianic age. It is about the time when Israel is redeemed. If you follow the text, the kings of the world are speaking at the beginning. They are now recognizing the wrongs they committed against Israel and cannot believe that Israel was right after all this time. They are healed, as in brought to HaShem, through Israel's suffering and eventual redemption.
Now that you mention it, let's look one page back and see what it says.
Isa 52:13-15 Behold, my servant shall deal prudently, he shall be exalted and extolled, and be very high. (14) As many were astonied at thee; his visage was so marred more than any man, and his form more than the sons of men: (15) So shall he sprinkle many nations;
the kings shall shut their mouths at him: for that which had not been told them shall they see; and that which they had not heard shall they consider.
So before going into a discussion on how Israel will treat the Messiah, the scripture teaches that the kings of the nations "shall shut their mouths at him: for that which had not been told them shall they see; and that which they had not heard shall they consider." IOW, the Gentiles, who never had the prophecies of the Old Testament to accept any such thing, shall hear the Gospel, and consider it. This then goes into the next chapter, which talks of the Messiah being rejected of men. IOW, rejected by His own people, yet He carries their sins upon Himself, by which He makes many righteous, and shall see His offspring.
This is the Gospel message, pure and simple, and is an accurate prediction of what in fact happened.