Gethsemane means ‘the oil press’. David could say, ‘I am like a green olive tree in the house of God’ (Psa. 52:8). Israel in her long history could say the same. But the suffering Saviour could say it best of all, for there in Gethsemane – the oil press – he was crushed and bruised without mercy. But how and why? How is the sudden and dramatic change of atmosphere between the upper room and Gethsemane to be explained, even in a measure? Christ knew all along the death that awaited him. He had grappled with Satan and his legions more than once. He had repeatedly spoken of his death to his disciples, telling them what that death would accomplish. He had prayed with the utmost confidence in his high priestly prayer (John 17). Why, then, is there this sudden plunge into such awful agony, why this shuddering horror? Why is this fruit of the olive tree so severely crushed? Why does the divine record say that in Gethsemane our Lord BEGAN to be sorrowful, sorrowful in a new and terrible way? Was it not because God began forsaking him then? How else is this sorrow unto death to be understood?
‘Jesus wept’, but never like this. No previous sorrow of his could match this. At the time of his arrest he declared, ‘Shall I not drink the cup which the Father has given me?’ (John 18:11). That cup was constantly in view as he prayed in Gethsemane. What cup? ‘THIS CUP’ – not some future cup. The cup that was symbolized in the feast (Matt. 26:27, 28) was now actual: God was placing it in the Saviour’s hands and it carried the stench of hell.
The Cross He Bore: Meditations on the Sufferings of the Redeemer by Frederick S. Leahy, p. 4-5 (2007)