Toldot: Yaakov's Deceptive Words to Yitzhak

We look at the episode of Yaakov impersonating Esav, and focus on the issue of Yaakov lying.  How could Yaakov lie to his father? We grapple with the problematic nature of a type of comment by Rashi.

Rashi comments that Yaakov’s words were technically possibly not lying, though he still misled his father. This type of comment is troubling, though. Yaakov is still deceiving his father – and still essentially lying. One could argue that lying is justified in this context, but is the idea of formulating words in a clever manner really better? The problem of lying is about communication with deception.