WORD STUDY –  CUP
Psalms 16:5 “The Lord is the portion of my inheritance and my cup, thou maintains my lot.” Psalms 23: 5b “Thou anoints my head with oil, my cup runneth over.”
Cup – Hebrew: kavas – cup, pelican or stork
The word “cup” in Hebrew is “kavas,” which has a double meaning, a cup and a pelican or stork. To us in the Western World, a pelican is a strange looking bird with a long beak connected to a pouch who is always eating fish.  We see nothing special.  Yet to the ancient world a pelican and stork were considered the same bird and both were noted for the tender care of their young.  They would even care for the young that was not their own.  Hence, you have the legend of a stork delivering a baby.  There was also the belief that when food was not available for its young, the pelican would feed its young on its own blood.  There was also the ancient belief that if one of its young died, the mother pelican would resurrect it with her own blood.   If David was making a play on words here, the use of “kavas” would show a strong Messianic prophecy.
“Kavas” or cup is spelled:  kap – empty mind filled with God’s thoughts,   vav – redemption, and samek – abundance, mysteries of God, protection.   In Psalm 16 when David says the Lord is his Cup he is say that God’s thoughts fill his mind and that God is his redemption and protection.   In Psalms 23 when he says that his cup overflows he is saying that he is overflowing with thoughts of God, His redemption and overflowing with an abundance of protection and knowing the mysteries of God.
The numerical value of cup (kavas) is 96 – kap =20, vav = 6, and samek = 60.   What other Hebrew words have 96?   One word is “damamim” which is blood or bleeding. In Aramaic this word means submitting to the will of God.  In Mark 4:39 Jesus told commanded the sea: “Peace be still.”  In the Syriac Bible which is the language Jesus spoke it uses the Aramaic word damam.  Jesus really commanded the sea to submit to the will of God.  Another word with a numerical value of 96 is  “vayoda’”  which is knowing in an intimate way.  David’s cup is an intimacy with God and in Psalms 23 he is overflowing in this intimacy.  The word “ezuuwz” also has a value of 96 and means “strength.”  The Lord is my  strength and in Psalms 23, we are overflowing with his strength.
His cup overflows with oil.  The word for cup is prefixed in the Hebrew with a “beth, pathah” and would be rendered, thou anoints my head in the oil.  The word for oil is “bashemen.”  Oddly  this is not “yitshar” which is an anointing oil.  Bashemen comes from the root word “shaman” which means to be fat, or rich.  It is also used to express an oil used for medicinal purposes.   The word anoint is “dishaneth” which is in a piel form and has the idea of making something fat.  You could render, “you anoint my head with oil” as “You make fat my fat,” or in a piel form “You make my head so fat it is obese.”   Actually, this creates the idea of abundance in success.
When David says “thou prepares a table for me in the presence of my enemies” he is referring an ancient oriental custom where you invite an enemy over for dinner if you wish to make peace and/or reconcile with him.  Thus David is saying you make reconciliation with my enemies and as a result I am prosperous and an overwhelming success.
Thus, when David said his “cup runs over”  he is saying that God has made him an overwhelming success, prosperous, healthy and at peace with those around him. And if we throw in the pelican we realize that this is all accomplished through the blood of Jesus Christ and his redemption.
May your cup overflow.