In Psalm 23:5 the sheep says, “You have anointed my head with oil.”
It was the custom at the end of the shepherd’s day that he would find a little alcove somewhere, in an outcropping of rocks or trees, a sheepfold, and he would position himself at the gate as a sentry. And one by one as the sheep would come in, as they would pass under the rod to be “counted,” the shepherd would inspect them and look at their head for any scratches, or cuts, or bites. He would then take a homemade oil concoction, perhaps of olive oil and cedar tar and smear it on those booboos. There was an antiseptic quality in that, there was a soothing, balming quality in that. It was a beautiful intimacy as the shepherd is inspecting and caring for every aspect of that sheep.
But there’s a higher level to that oil. We see in the Old Testament that the idea of the oil is the presence of God’s Spirit upon any given individual. For the High Priest it was a special oil made of the most precise and precious ingredients (Exodus 30:23-25). When the prophets, and the priests, and the kings, and the commanders were chosen for an assignment, they would be anointed with oil; that was an affirmation that God’s Spirit was with them on their journey, in their task.
We see the beautiful vision of that in the Messiah, the Anointed of God, the Christ, the one who is anointed for a very special mission. I believe what’s being communicated in Psalm 23:5 is the beautiful intimacy of God’s Holy Spirit with those who are counted among the flock of God.
To be covered then, to be anointed is to enjoy the surrounding favor and presence of the Lord, around, upon and within the Sheep of His pasture.
“You have anointed my head with oil. My cup overflows.” David is simply communicating, “I understand the true depth of relationship I have with you – and it is beautiful.” The sheep appreciates the full measure of blessings that he is reaping because the Lord is his Shepherd.