Most Jewish people today believe that Isaiah 53 isn’t talking about the Messiah, but about the nation of Israel, suffering at the hands of the world. Some rabbis will even claim that this was always Judaism’s view. However, all ancient Jewish writings, the Mishna and Gamara (Talmud) and the Midrashim, as well as other manuscripts, saw the passage of Isaiah 53 as a passage talking about the Messiah, not the nation of Israel. So which is it?
Jewish sages preceding the medieval scholar, Rashi, all believed this passage to be a description of the Messiah, so when Rashi controversially first suggested that Isaiah 53 was about Israel some time around 1050 CE, the Jewish community did not receive his new interpretation positively. Even Maimonides opposed it.[1]

Jewish sages saw Isaiah 53 as speaking of an individual, not plural:

• Targum Jonathan interprets Isaiah 53 with reference to the Messiah (singular).
• The Talmud never interprets Isaiah 53 with reference to the nation of Israel (as a whole), but only to individuals within It.
• The Jerusalem Talmud (Tractate Shekalim 5:1) applies 53:12 to Rabbi Akiva (singular), while the Babylonian Talmud applies 53:4 to the Messiah (singular) in Sanhedrin 98b, 53:10 to the righteous in general in Tractate Berakhot 5a, and 53:12 to Moses (singular) in Tractate Sotah 14a.
• Midrash Rabbah interprets 53:5 with reference to the Messiah (Ruth Rabbah 2:14).
• Yalkut Shimoni applies 52:13 to the Messiah.[2]

However, once Christian missionaries started using Isaiah chapter 53 widely as a strategy to prove that Jesus is the Messiah, the number of rabbis accepting Rashi’s interpretation as an easy solution grow dramatically up to the point where today, the idea that it pertains to Israel is the most accepted interpretation of Isaiah 53.
Rabbi Daniel Asur, in his book,  “Singular and plural uses in Isaiah chapter 53, and Christianity’s Linguistic Failure in its Interpretation” admits that, “There are 67 expressions in chapter 53 that speaks of the singular”, but still assures his readers that Isaiah is merely “speaking poetically about the nation of Israel as of the singular”. He bases his argument on verses 8 and 9, where Isaiah is using plural instead of singular. Let's look at these two instances more closely.

“Lamo” (לָמוֹ) in Isaiah 53 verse 8

Rabbi Daniel Asur claims that according to verse 8, the character described as plural, not in singular, and therefore cannot be talking about the Messiah. He writes (from Hebrew): “The word ‘Lamo’ means ‘them’, and instead of the prophet writing ‘for the transgression of my people ‘he’ was punished’, he writes ‘Lamo’, meaning the servant is plural… that is why it is not possible for Jesus to be the Messiah.”
However, there are a few other possible aspects that Asur fails to acknowledge:

1. “Lamo” can be either plural or singular, as Isaiah elsewhere uses lamo to mean “to it,” not “to them,” Isaiah 44:15: “he makes an idol and bows down to it”. So, if we take lamo to refer to the servant, it could still mean “for him” as opposed to “for them.”
2. Septuagint (LXX): εἰς θάνατον (לַמָּוֶת) – The translators of the Septuagint saw a taf at the end of “lamo,” making it “lamavet” – to death. “He was led to death”.
3. NJPSV (New Jewish Publication Society Version) understood “nega‘ lamo” as
   “For the transgression of my people to whom the stroke was due”. The servant receives a stroke for those for whom he is suffering.

So then, we can see that the Messiah can fit perfectly with verse 8 in Isaiah chapter 53.

“Bemotayv” (בְּמֹתָיו) in Isaiah 53 verse 9

The second time rabbi Asur “noticed” a plural description is in verse 9, where he believes the character is dying multiple deaths, not a single one, and therefore, cannot be the Messiah. He writes (from Hebrew): “Any Hebrew speaker will be amazed. Why does it says “Bemotayv” and not “Bemoto”? How come the word “Moto” in singular does not appear here, yet  the word in plural, “Bemotayv”, does? Meaning the servant in Isaiah 53 experienced several deaths, not just one. Didn’t Jesus died only one famous death?…It is clear that the term “Bemotayv” in the bible speaks of plural not singular”.  
However, both in biblical Hebrew and in modern Hebrew, a word written in plural form doesn’t always mean more than one referent, but may also indicate collectively (intensive plural). For example: פניו (Panayv) רחמים (Rahamim) אדוניו (Adonayv) are all in plural form, yet have a singular meaning to them.
Jewish scholar of Semitic languages, Dr. Michael Brown, agrees: “Such usage of intensive plurals is extremely common in Hebrew, as recognized by even beginner students of the language.”
There are only two occasions in the Hebrew Scriptures where “death” in plural exists: (1) Isaiah 53:9. (2) Ezekiel 28:10 (מוֹתֵי עֲרֵלִים תָּמוּת). Ezekiel 28:10 clearly states that Ezekiel is using plural deaths (מוֹתֵי) in order to describe a singular death (תָּמוּת).
Now, let us see how bible translators in modern and ancient times understood this verse:

1. As found at the Dead Sea Scrolls, this verse was written (before Jesus existed) in the singular: “בומתו”.
2. The Jewish sages translating the Septuagint, also understood this verse as talking about the singular, translating it:  ἀντὶ τοῦ θανάτου αὐτοῦ = בְּמוֹתוֹ (death in singular).
3. The NJPSV (New Jewish Publication Society Version) translated: “And with the rich his tomb”. Modern Jewish version, although they took out “death”, they still choose to translate verse 9 as in the singular, not plural.
4. The Targum (Jonathan ben Uzziel) a Jewish translation into Aramaic translated “Bemotayv” into the singular (בְמוֹתָא) and not into the plural (בְמוֹתָיא).

If prophet Isaiah meant the death to be in the plural, he probably would have used “בְמוֹתָ֖ם” such as appears in 2nd Samuel 1:23 (see also Ezekiel 28:10)
Is Asur about to accuse the Prophet Ezekiel as well as the interpretations by Jewish sages of ancient times as being “failures”? Or perhaps Asur would like to blame The Jewish Publication Society as trying to force their Jewish translation to fit Jesus?
Isaiah chapter 53 continues to shout the name of Jesus-Yeshua through the sufferings and death of the Messiah for our sins as a testimony of God’s love for us!

[1] Maimonides (1135-1204), one of the most famous rabbis of all time, in a letter to Jacob Alfajumi, stated: “What is to be the manner of Messiah’s advent, and where will be the place of His first appearance? . . . And Isaiah speaks similarly of the time when he will appear…He came up as a sucker before him, and as a root out of dry earth, . . . in the words of Isaiah, when describing the manner in which the kings will hearken to him, at him the kings will shut their mouth; for that which had not been told them they have seen, and that which they had not heard they have perceived.” In this quote, Maimonides applied Isaiah 52:15 and Isaiah 53:2 to the Messiah.
The Fifty-Third Chapter of Isaiah According to the Jewish Interpreters, Translation: S.R. Driver and A.D. Neubauer, (KTAV publishing House, New York, 1969) pp. 374-375
[2] Michael L. Brown, Answering Jewish Objections to Jesus, Volume Three – Messianic Prophecy Objections (Grand Rapids: BakerBooks, 2003), pp. 49-57.