Until the 11th century commentaries of Rashi, Isaiah 53's 'Suffering Servant' was understood to mean Messiah NOT Israel.

Scripture gives opposing views of Messiah; Messiah was to be rule the world, yet Messiah was also to suffer for the sins of mankind. Early rabbis, unable to conceive of one Messiah fulfilling both roles, often relied on the "two-Messiah" theory: one Messiah was Messiah ben Yosef, who suffered; and the other, Messiah ben David, who ruled, and would establish the promised messianic kingdom. Even at the time of Yeshua (Jesus), it was the hope of King Messiah ben David that warmed the oppressed Israelites' hearts - a king who would overthrow Roman rule and liberate Israel.

This was certainly the hope of Yeshua's disciples as well. But Yeshua revealed to them with Scripture that Messiah was to suffer first. While we all look hopefully for the arrival of King Messiah, we must honestly deal with Scripture teaching a Suffering Messiah, since it is only through Messiah's sufferings that man finds complete atonement and justification from G-d.

Yeshua very clearly fulfilled the Suffering Servant passage of Isaiah 52/53. But for this reason, modern Judaism now claims the passage isn't Messianic, but instead, is about Israel. An honest reading of the text will show the passage cannot be about Israel.

Let's look at earlier rabbinic thought which proves that Isaiah 53 was previously understood by Judaism as a messianic prophecy - that Judaism originally expected a 'suffering' Messiah:

"Messiah son of Joseph was slain, as it is written, "They shall look unto me whom they have pierced; and they shall mourn for him as one mourneth for his only son" (Zech xii 10 (Suk. 52a))

"The Holy One gave Messiah the opportunity to save souls but to be severely chastised: and forthwith the Messiah accepted the chastisements of love, as is written, 'He was oppressed, and he was afflicted.' And when Israel is sinful, the Messiah seeks mercy upon them, as it is written, 'By his stripes we were healed,' and 'He carried the sins of many and made intercession for the trangressors.'" (Bereshith Rabbah, Rabbi Moshe Hadershan)

"The word 'man' in the passage refers to the Messiah, the son of David as it is written, 'Behold the man whose name is Zemah'; there Jonathan interprets, Behold the man Messiah; as it is said 'a man of pains and known to sickness.' (Midrash Thanhumi, Rabbi Nahman)

Rabbinical Elijah the prophet quote: "Bear the suffering and punishment of thy Lord, with which he chastises thee for the sins of Israel, as it is written, 'He is pressed for our rebellion - crushed for our iniquities' until the end come." (Midrash Cohen, BhM, 2:29)

The Talmud explains: "The Messiah--what is his name? Those of the house of Rabbi Yuda the saint say, the sick one, as it is said, 'Surely he had borne our sicknesses'." (Sanhedrin 98b)

"It is because of this future ordeal that David (prophetically) wept, saying My strength is dried up like a potsherd [Psalms 22:7]. At this hour, G-d will say to Him, Ephraim, My Righteous Messiah, didst Thou not agree before the creation to this? Now let Your sorrows be as My own sorrows....At that Messiah answers, Now is My Spirit calmed for 'It is enough for a servant to be like master.'" (Pesikta Rabbati Piska 36:142/Yalkut on Isaiah 60:1-2)

"Then He [My Servant Messiah] will become despised, and will cut off the glory of all the Kingdoms; they will be prostrate and mourning, like a man of pains, and like One destined for sickness; and as though the Presence of the Shekinah had been withdrawn from us, they will be despised, and esteemed not." (Targum Jonathan Isaiah 53:3)

"And when Israel is sinful, the Messiah seeks for mercy upon them, as it is written, 'By His stripes we were healed, and He carried the sins of many; and made intercession for the transgressors'." (B'reshith Rabbah)

Referring to Zech 12:10-12, "R. Dosa says: '(They will mourn) over the Messiah who will be slain.' " (B. Suk. 52a; also Y. Suk. 55b)

A late 10th century commentary of Isaiah 53 reads:

"As for myself, I am inclined with Benjamin of Nehavend, to regard it as alluding to the Messiah ...In the first instance that the Messiah will only reach his highest degree of honor after long and severe trials; and secondly, that these trials will be sent upon him as a kind of sign, so that, if he finds himself under the yoke of misfortunes while remaining pious in his actions, he may know that he is the designated one." (Yepheth ben All)

The Zohar:

"The Messiah, on his part, enters a certain Hall in the Garden of Eden, called the Hall of the Afflicted. There he calls for all the diseases and pains and sufferings of Israel, bidding them settle on himself, which they do. And were it not that he thus eases the burden from Israel, taking it on himself, no one could endure the sufferings meted out to Israel on account of their neglect of the Torah. So Scripture says, 'Surely our sickness did he bear' ... 'As long as Israel dwelt in the Holy Land, the rituals and sacrifices removed all those diseases from the world; now the Messiah removes them from the children of the world'." (Zohar 2:212a)

Rabbis:

"I will now proceed to explain these verses of our own Messiah, who G-d willing, will come speedily in our days. I am surprised that Rashi and Rabbi David Kimchi have not, with the Targums, applied it to the Messiah likewise." (Rabbi Naphtali ben Asher Altshuler, ca. 1650 A.D.)

"I am pleased to interpret it in accordance of our rabbis, of the King Messiah, and will be careful, so far as I am able, to adhere to the literal sense: thus, possible, I shall be free from the fancied and far fetched interpretations of which others have been guilty...." (Rabbi Moshe Kohen Ibn Crispin of Cordova and Toledo in Spain, ca. 1350)

"Our rabbis of blessed memory with one voice accept and affirm the opinion that the prophet is speaking of the King Messiah. And we ourselves shall also adhere to the same view." (Rabbi Moshe Le Sheich, second half of the 16th century)

"But he was wounded...meaning that since the Messiah bears our iniquities which produce the effect of His being bruised, it follows that whosoever will not admit that Messiah thus suffers for our iniquities, must endure and suffer for them himself." (Rabbi Elijah de Vidas)

The above was borrowed from Light of Mashiach