Why did they give Jesus vinegar at the cross?

At the crucifixion, Jesus was offered something to drink more than once, and it is helpful to note what the liquids were each time. The KJV calls the basic ingredient “vinegar”; other translations speak of “sour wine” (NKJV), “wine vinegar” (NIV), or simply “wine” (ESV). At least once, the vinegar was mixed with another substance.

The drink in question was posca, a low-quality, acidic beverage that was the common drink of Roman soldiers and the peasantry. Posca was made of diluted vinegar—which undergoes a fermentation process similar to that of wine—and probably some type of herbal flavoring.

The first offer of vinegar to Jesus.
Matthew 27:33–35 says, “And when they were come unto a place called Golgotha, that is to say, a place of a skull, They gave him vinegar to drink mingled with gall: and when he had tasted thereof, he would not drink. And they crucified him” (KJV).

In Mark 15:23, the same drink is called “wine mingled with myrrh” (KJV). The gall or myrrh was a drug that acted to dull the sense of pain. There was “a jar of wine vinegar” at the ready (John 19:29), and it seems that this particular mixture of vinegar and gall was often given to those about to be crucified as an act of mercy to ease the pain of their death. Jesus refused this gall-laced potion after He tasted it and realized what it was. The Son of Man, in dying on our behalf, rejected anything that would numb the suffering our salvation required. To accept the stupefying vinegar-and-gall mix would lessen sin’s punishment. Jesus courageously refused to take the easy way out (see Isaiah 53:10).

The second offer of vinegar to Jesus.
After Jesus had been nailed to the cross, He was offered vinegar again. This time, it was part of the scorn and derision Jesus endured as He hanged suspended between heaven and earth. Luke records how the bystanders were mocking Christ, and “the soldiers also mocked him, coming to him, and offering him vinegar, And saying, If thou be the king of the Jews, save thyself” (Luke 23:36–37). It could be that the soldiers were only pretending to offer Jesus a drink to ease His thirst, cruelly taunting Him with relief.

The third offer of vinegar to Jesus.
After the three hours of darkness, and just before Jesus’ death, they offered Jesus vinegar again. This time, He drinks some: “Jesus knowing that all things were now accomplished, that the scripture might be fulfilled, saith, I thirst. Now there was set a vessel full of vinegar: and they filled a sponge with vinegar, and put it upon hyssop, and put it to his mouth. When Jesus therefore had received the vinegar, he said, It is finished: and he bowed his head, and gave up the ghost” (John 19:28–30, KJV; cf. Matthew 27:45–49; Mark 15:33–36).

Someone near the cross heard Jesus’ statement, “I thirst,” and decided to give Him a drink. He extended a sponge full of wine vinegar to Jesus’ parched lips on a hyssop reed. Jesus took enough of the liquid to wet His vocal apparatus and made a final pronouncement: “It is finished!” A moment later, He was dead.

The offer of vinegar to Jesus prophesied.
Psalm 22:15 prophesies Jesus’ extreme thirst on the cross. Then, in Psalm 69, David laments the mistreatment he suffers at the hands of his enemies. In the middle of the psalm are these startling words:

So, Psalm 69:21 specifically mentions vinegar and gall, and the prophecy finds its fulfillment in Jesus’ death on the cross. In this way, David’s Greater Son experienced what David himself experienced—but to an infinitely greater degree.