26 Now as they led Him away, they laid hold of a certain man, Simon a Cyrenian, who was coming from the country, and on him they laid the cross that he might bear it after Jesus.
27 And a great multitude of the people followed Him, and women who also mourned and lamented Him. 28 But Jesus, turning to them, said, “Daughters of Jerusalem, do not weep for Me, but weep for yourselves and for your children. 29 For indeed the days are coming in which they will say, ‘Blessed are the barren, wombs that never bore, and breasts which never nursed!’ 30 Then they will begin ‘to say to the mountains, “Fall on us!” and to the hills, “Cover us!” ’ 31 For if they do these things in the green wood, what will be done in the dry?”
Luke 23:26-31
After the mocking, beating, and scourging, a bloodied and physically broken Jesus makes His way to Calvary for crucifixion. The Romans called upon Simon of Cyrene to aid Christ in carrying the cross. I see Matthew 11:28-30 here, a physical cross likely was not a light burden, but God always provides when we need Him and Jesus certainly needed the Father at this time.
28 Come to Me, all you who labor and are heavy laden, and I will give you rest. 29 Take My yoke upon you and learn from Me, for I am [a]gentle and lowly in heart, and you will find rest for your souls. 30 For My yoke is easy and My burden is light.”
Matthew 11:28-30
It was also a clear representation of what it truly means to bear your cross and follow Christ.
As the crowd followed, a group of women grieved for Him, mourning and lamenting. Here Jesus broke the silence that had persisted until now. I can take His statement two ways, first being a prophetic view of our modern world where in fact women are prided on not bearing children, focusing on career instead of family, and elevated for supporting the murder of offspring.
A mountain falling upon us all would be a mercy for what our society has allowed.
The second way I see it was also prophetic but focused on Israel. Jesus Christ was walking the earth, the Messiah had come to Jerusalem. The kingdom was at hand, the wood was green, times were good – then still the Romans and the Sanhedrin crucified the Messiah in these good times. In the years ahead, the children of that generation would suffer greatly, so much so they might consider those women who never bore children to see them suffer – blessed.
A mountain falling upon them would have been a mercy.
So He said “do not weep” for Him, weep for those subject to the darkness that would be coming for Israel in the years ahead, when the wood is dry. I also wonder if “the wood” here was a literal reference to the wood of the cross he bore.