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Missed Opportunity ~ Abraham's Greatest Regret
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After Abraham separated from Lot, Yahveh appeared to him and promised:
 
"Lift up your eyes and see, from the place where you are, northwards and southwards and eastwards and westwards. For all the land that you see, to you I shall give it, and to your descendants, forever. And I shall make your descendants like the dust of the earth, that if a person can count the dust of the earth, so shall he number your descendants. Arise and walk about in the land, its length and breadth, for I shall give it to you."  Genesis 13:14-17
  
This promise applied not only to the land of Canaan, but to the great expanse from the river of Egypt up to the river Euphrates. We usually think of these verses as a promise for the future, but it is not so. Yahveh's intention was for the present. Indeed, immediately after this promise was given, the kings from the other side of the river Euphrates invaded the eastern side of the Jordan River and attacked all the Kingdoms there.
 
Along came Abraham and defeated them. In banishing them and the remains of their forces to the other side of the river Euphrates, all the land up to the Euphrates fell into his hands. Thus Yahveh fulfilled His promise to Abraham, to give the entire land into his hands.

But Abraham withdrew...
 
He returned to his tent and relinquished his rulership over this vast area that Yahveh gave him. He obviously had his reasons: ruling over the land meant assuming responsibility for its inhabitants and educating them in the ways of Yahveh. Abraham saw the men of Sodom in all their wickedness, and concluded that he was not up to the task. Thus he failed in the challenge that Yahveh placed before him. 
 
Abraham's regrets over his decision are easily detected in his prayer to save the people of Sodom some twenty-four years later, and Yahveh’s comforting response to him:
 
"After these things Yahveh's Word came to Abram in a vision, saying: Do not fear Abram; I am your Shield, and your reward is very great."  Genesis 15:1
  
What did Abraham fear? He feared that he lost his reward as well as Yahveh's promise, since he himself decided to forego it. Therefore Yahveh once again promised him the land, and Abraham, this time, requested a covenant rather than just a promise:
"By what shall I know that I will inherit it?"