I have been chewing on Psalms 16:5 for a season now, and quite frankly I've been puzzled by this verse. I went to the Blue Letter Bible online to find out what each word really means in the original Hebrew. http://www.blueletterbible.org/Bible.cfm?b=Psa&c=16&v=1&t=KJV#top
Here is the verse 5 with the Strong's numbers attached to each of the words with definitions.
The LORD 3068 [is] the portion 4490 of mine inheritance 2506 and of my cup 3563: thou maintainest 8551 my lot 1486.
So after many days of looking at this verse and all the verses surrounding it for contextual meaning, I was still a bit puzzled about why it says that the Lord is like my parcel of land and linked to a cup. I originally thought the word lot at the end of this verse meant like a parcel of land but rather it means the winnings in casting of lots.
So this verse says:
The LORD is my assigned parcel of land or reward AND my cup: The LORD maintains or holds in place my winnings from playing a game of chance.
It was common in bible times to cast lots to make a difficult decision (Matthew 27:35; John 19:24; Acts 26:10) It was the fair way assign a ministry position when choosing a person from a group when everyone is an equally qualified. They did this to choose someone to replace Judas after he hanged himself. There were many good candidates and they cast lots to pick from the group.
I really wanted to understand the full meaning of this passage of Scripture so I went to prayer about it. While praying in the Spirit, I kept hearing the Lord say, "You can't lose!" and I also heard in my spirit. "You hit the jackpot 100% of the time when you are in Me."
So the Lord convinced me it is safe and proper conclusion that verse 5 is saying that the Lord is the one who holds in place how the coin toss or lots fall. Does this really say, we can't lose with God as our reward as we are guaranteed success? That is some pretty incredible FAVOR from God.
When we KNOW or he has SHOWN us who He is (or yada-- a very intimate form of knowing Psalms 16:11) then it is like hitting the jackpot! I'm a winner! The game is rigged so I end up with all the loot or spoils in this life. The spoils do not have to be monetary. The spoils can be the salvation of our loved ones or a loss of relationship that we so dearly want restored. The spoils can be a lost opportunity in ministry.
I know the devil has ravaged so many of God's people but maybe we let the devil get away with our good stuff because we didn't know that we are guaranteed to win. God has maintained or held in place the outcome of our life.
Read verse 11 in Psalms 16.
You reveal the path of life to me;
in Your presence is abundant joy;
in Your right hand are eternal pleasures.
in Your presence is abundant joy;
in Your right hand are eternal pleasures.
So if you have been dealt a bad hand in this game of life you can just trade those cards in and get some better ones. If it is true that the LORD is your assigned portion and cup and he rigs the game in your favor then why wouldn't we just trade in the cards that we were first dealt?
Is this too good to be true? Is the writer of this Psalms laying it on a bit thick about how amazing our relationship with the LORD truly is to us as believers? This Psalm is written by someone who experienced God from the Old Covenant. David experienced God from the standpoint of being under the Law.
We are told in Hebrews 7:22 that we have a better covenant with God.
"Because of this oath, Jesus has become the guarantee of a better covenant."
Jesus paid the whole price for our eternal security in Christ. WE CANNOT LOSE!!!!