Cigars and insurance, what does this English joke mean?

A buddy in North Carolina, USA, bought an expensive box of cigars and then insured the cigars, including fire insurance. Later, it really happened. Although I didn't start paying the insurance premium, I finished smoking cigars within one month. He thought of a way to claim compensation from the insurance company, claiming that his cigar was completely lost in "a series of small fires". The court held that the insurance company's terms were not clear about what kind of "fire" could be exempted, and ruled that the insurance company should compensate the buddy 15000 USD for the cigar damaged by "small fire".

The insurance company was in a hurry and counterclaimed that the buddy deliberately set fire to the insured cigar for 24 times on the grounds of claim. The court sentenced the man to two years in prison and fined him $24,000.

This joke tells us that cleverness is mistaken by cleverness.