What does Genesis 25:26 mean?

The first twin emerged both red and hairy. His name, Esau, somehow describes his hairiness. The second twin is neither red nor hairy, compared to his twin, but he is also named for his first impression on his parents. He comes into the world grabbing his brother's heel. The Hebrew word for heel is 'aqeb, and so this child is named Ya'aqob, or Jacob, literally meaning "he clutches the heel." Interestingly, though, and also important, Jacob can mean "may God protect or reward," or—unfortunately for Esau—it can also mean "usurper."

Interestingly, in English at least, the phrase "pulling my leg" means "joking with me," or "lying to me." Jacob's future will be heavily influenced by acts of deception (Genesis 25:29–34; 27:30–35). Some of those will be at his own expense (Genesis 29). While there's no direct connection between his Hebrew name and the English idiom, Hebrew verbs similar to Jacob's name refer to those who "watch from behind" or "trip up" others, a reference to trickery. In practical terms, Jacob's life is loaded with incidents of usurping—both in his favor, and to his disadvantage.

We're now told that Isaac was 60 years old when the twins were born. These babies, as troubled as their relationship might be, were a direct answer to Isaac's prayer that his wife would become pregnant. After 20 years of childlessness, the couple were finally parents, twice over, and Abraham—now 160 years old—can finally glimpse the next generation of the covenant entering the scene.