Isaiah 53 Suffering Servant Questions

He was despised and rejected—a man of sorrows, acquainted with bitterest grief. We turned our backs on him and looked the other way when he went by. He was despised, and we did not care.
Yet it was our weaknesses he carried; it was our sorrows* that weighed him down. And we thought his troubles were a punishment from God for his own sins!
Holy Bible : New Living Translation. 1997 . Tyndale House: Wheaton, Ill.

Was Jesus acquainted with bitterest grief and sorrows before He took up our weaknesses?

It occurs to me that this passage may imply that Christ knew sorrow prior to taking our infirmities upon him.

What might Jesus’ sorrows have been, i.e. His sorrows which were his alone and apart from mankind?

I have always thought that Jesus only knew grief, vicariously through mankind.
But, what if He knew grief in His own right; what if He experienced personally a grief that was unique to Him and His own life, would that make a difference on how I perceive my Lord?
It seems to make a difference to me.
Does it make a difference to you?

It is a curiosity.

God bless,
DSM