The man who stole a truck of rubber bands

This joke is a prime example of humor built on clever wordplay, specifically a pun that perfectly connects two seemingly unrelated concepts. The entire gag hinges on the phrase "a long stretch," which is designed to make you think about the physical properties of the stolen goods. Rubber bands, by their very nature, are meant to extend and stretch a considerable distance, creating a funny mental image of endless elasticity.

However, the real twist, and where the legal category comes into play, is the second meaning of that exact same phrase. In common slang, particularly within discussions of crime and punishment, "doing a stretch" or "getting a long stretch" refers to serving a lengthy prison sentence. So, the joke playfully links the stretchy nature of rubber bands to the prolonged period of incarceration awaiting the unfortunate thief, implying he'll be locked up for a good, long time. It’s a neat linguistic trick that takes us from bouncy bands to serious hard time with just a few words.