Pirates of the Plain centers around a nine-year-old boy with an overactive imagination. Whether it's shoot-outs with the James Gang or laser battles with alien robots, little Bobby's playmates seem real to him. It frightens his mother , while Bobby's grandpa thinks it's just Bobby's way of coping with not having many friends and a father that left him two years prior. At the same time that Bobby's story unfolds, a pirate captain in 1732 called Jezebel Jack has run afoul of his crew of cutthroats. Jezebel Jack has a map to a king's ransom worth of treasure but he wants it all for himself. After killing a man who knew the captain wasn't willing to share, Jack is thrown overboard by the rest of the pirates, and ends up in the wheat fields of Nebraska near Bobby's family's farm! As the two unlikely friends go on a treasure hunt for a strong'-box of silver bars hidden by wild west outlaws, the disgruntled crew of Jack's ship, Delilah, also ends up "sailing the amber waves of grain."