Wrongway Feldman was a World War I pilot, who had a reputation for going the wrong way, even bombing his own airfield, thus his nickname; he was considered the most incompetent airman there ever was, or at least pretending to be that incompetent. His first name is unrevealed, but he was often accompanied by his wing-man, Bucky Lorenzo, who was almost as incompetent as Wrongway, if not worse. He flew an old Bristol Scout biplane in the United States Army Air Corp during the war, and afterward, he acquired a second biplane known as The Spirit of the Bronx.
According to Thurston Howell, Wrongway got his nickname much later while flying for Howell Aviation by setting a record for flying from Chicago to New Orleans when he was supposed to fly to Minneapolis from Chicago. After the war, Wrongway disappeared during a flight from around the world from New York, but he actually got lost and retired to a remote island in the South Pacific in 1934. Roughly a month after Gilligan and the Castaways became stranded on the island, they discover Wrongway still clad in his pilot's leather helmet, scarf and leather coat living on the island. They restored the Spirit of the Bronx to get it working again, but a mysterious figure started vandalizing the craft. After the men started guarding it, Wrongway mysteriously vanished, apparently abducted by someone, but Gilligan discovered it had all been faked. Terrified to get into the air again, Wrongway confessed he had been vandalizing his own plane to keep from flying, but when Gilligan offered to fly it, he started taking flying lessons from him in secret. However, at the last minute, Wrongway realized Gilligan couldn't make the trip and replaced him, leaving the island for the first time in thirty years.
Back on the main land, Wrongway finds himself an instant celebrity, but his efforts to rescue the others are complicated by the fact no one can decipher his notes. On the other hand, Wrongway finds civilization much different and more progressed than he left it. People are more rude, cities are louder and more commercialized and he can't get a steak the way he likes it. Retrieving The Spirit of the Bronx out of a museum where it ended up, he flies off looking for peace and quiet and somehow ends up back on the island again. His stories of being back home only make them more desperate to be rescued. He upsets both Mr. Howell, whose New York rents are the lowest during a money-making bonanza, and Ginger, whose old roommate, Debbie Dorson, is now a Broadway star. They try to get Wrongway to fly back for help, but he considers the island a paradise and doesn't want to leave the island. After a series of faked medical emergencies fail, the Castaways try to ruin paradise by over-working Wrongway, refusing him food and over-crowding him. When he feels he has finally had enough, he flies off to Hawaii get away from them, but instead, he gets lost and ends up on a another island unaware the island he lands on is Hawaii, where he's finally treated in a manner he's accustomed.
Despite his disappearance, Wrongway still stays in the minds of the Castaways. Years later, after leaving the island and returning to it, Mr. Howell makes a reference to him after discovering relics of the United States Air Corp on the island.
Gilligan tells Wrongway that he missed World War II, who in turn reveals he wondered what the noise was. However, later episodes and the second movie reveals the island was once used as a landing strip during World War Two, which makes one wonder how Wrongway eluded discovery during those years.
Among his provisions was 64 bottles of scotch.
Unlike most later visitors to the Island, Wrongway actually alerts the world of being on an Island with the castaways without naming their names; unfortunately, his directions are so mixed up that the Island is located anywhere from the Bay of Naples to the Arctic Circle.