As the U.S. tariff act of June 6, 1872, was being drafted, planners intended to exempt “Fruit plants, tropical and semi-tropical for the purpose of propagation or cultivation.”

Unfortunately, as the language was being copied, a comma was inadvertently moved one word to the left, producing the phrase “Fruit, plants tropical and semi-tropical for the purpose of propagation or cultivation.”

Importers pounced, claiming that the new phrase exempted all tropical and semi-tropical fruit, not just the plants on which it grew.

The Treasury eventually had to agree that this was indeed what the language now said, opening a loophole for fruit importers that deprived the U.S. government of an estimated $1 million in revenue. Subsequent tariffs restored the comma to its intended position.