As I go through Isaiah 53, I will highlight various words that appear elsewhere in the OT:
(53:4a) Surely he has borne our griefs and carried our sorrows
(11c) he shall bear their iniquities
(12c) yet he bore the sin of manySt Matthew (8:16-17) directly quotes verse 4a and applies it to Jesus healing the sick and casting out demons; it has nothing to do with Penal Substitution. The term "bore" (H5375) here also appears in verse 12c, and the term "carried" (H5445) also appears in verse 11c. What the parallel usage in 4a (and Mat 8:16f) shows is that the notion of 'bearing' need not be literal nor so called "imputation", but rather a way of simply saying 'takes away'.
(4b) yet we esteemed him stricken, smitten by God, and afflicted.
(7a) He was oppressed, and he was afflicted
Job 2:5 But stretch out your hand and touch his [Job's] bone and his flesh, and he will curse you to your face.Many Protestants read 4b as saying people thought ("esteemed" H2803) Jesus was being punished for His own sins rather than ours, but that's a serious distortion and quite unwarranted. In fact, it ties back to 53:2-3, where it says the Jews "esteemed" (same word) Jesus as a nobody, and at the Cross thought was under God's displeasure because God didn't come to His rescue (cf. Mat 27:40-43) - though these folks were obviously jumping to erroneous conclusions. The term "esteemed" in Hebrew is very frequently used in reference to people "reckoning" evil thoughts or plans against others, or even down right mistaken (Gen 38:15; 1 Sam 1:13). The term for "stricken" (H5060) is also applied to Job (where the Devil challenges God to touch/strike down Job), as is the term for "smitten" (H5221, where Job states he was 'smitten by God'), and finally, the term "afflicted" (H6031, where Job states he was afflicted/humbled by God). Keep in mind that though the English words might be slightly different at times (depending on Bible translation), the color-coded Hebrew words are the same, and the context clearly is using the words the same way as well.
Job 19: 21 Have mercy on me, have mercy on me, O you my friends,
for the hand of God has touched me!
Job 30:11 God has loosed my cord and humbled me
(5) But he was wounded for our transgressions; he was crushed for our iniquities; upon him was the chastisement that brought us peace, and with his stripes we are healed.
(10) Yet it was the will of the LORD to crush him
Job 6:9 that it would please God to crush meJob 5:17 blessed is the one whom God reproves; therefore despise not the discipline of the Almighty
As with the previous verse, a similar theme emerges: The Hebrew terms "crushed" (H1792) and "chastisement" (H4148) are applied to Job. One important note here, some translations render the term "chastise" as "punishment," but this is inaccurate since the term refers to fatherly correction and not a judicial punishment (note how frequently the book of Proverbs uses the term!). With that in mind, while the term "stripes" (H2250) doesn't appear in Job, the reference to Proverbs above shows it can fit the 'chastise' concept as well.Prov 20:30 Blows that wound cleanse away evil; strokes make clean the innermost parts.
The term "laid" (H6293) in Hebrew means to "encounter, meet, make intercession," and this is how it's used in verse 53:12c. Taking into account the parallel in 12c, the notion that should be drawn from 6b is that the Servant took upon Himself the burden to correct the sins, and interceded (not substituted) to make atonement. Examples of intercession (again, not substitution) appear all over the OT, for example: Jer 15:1; 18:20; Num 25:10-13; Deut 9:16-20.(6b) the LORD has laid on him the iniquity of us all
(12c) he bore the sin of many, and makes intercession for the transgressors
Conclusion: The purpose of this brief exercise is to show that just because someone - in this case the Suffering Servant - is having pain inflicted upon them, even by God's decree, that this automatically entails God's Wrath must be upon the individual, for that is a serious logical fallacy. The prime example of this false assumption being soundly disproved is that Job is explicitly described as being "stricken," "smitten," "afflicted," etc, by God - yet the very lesson of the Book of Job is that God caused all this suffering to fall upon Job yet God's Wrath was never upon him. Why can it not be the same for the Only Begotten Son of God, Jesus Christ? This is not to put Jesus and Job on the same plane, God forbid, for their status and merits are without comparison. Rather, Job would be a foreshadowing of a more excellent Person, Jesus Himself, which is something the Early Church Fathers saw very clearly.
For more information on how Isaiah 53 is incompatible with Penal Substitution, see Section 3a of this Essay.