Norbert Wiley is a career criminal, pick-pocket and con-artist who turns up on the island after hitting an underwater reef off shore. Not much is known about his life, but given his reputation for fabrication and exaggeration, much of his claims must be taken with a grain of salt. Wiley claims to have been so poor that he couldn't live in the slums as those were for "rich people." He was close to his father who had no job, and he always got stuck playing the cop in "cops and robbers" - never the good guy. He made his life robbing and stealing from others before turning to kidnapping. In 1962, he abducted Melissa Vandermere for $50,000. Wiley claims he left civilization to stop himself from breaking the law, but once on the Island, he kidnapped Mrs. Howell for $10,000, Mary Ann for $20,000 and Ginger for $30,000. The Skipper eventually captures Wiley and put him in a bamboo cage, but once jailed, he starts using flattery and compliments on everyone to get himself freed. Once out, he lifts everyone's valuables during a party celebrating his "going straight" and steals his repaired boat back. Meanwhile, the Castaways believe he has repented although the Professor has his reservations. When they hear Wiley starting up the boat and abandoning them, the Professor gets proven right as absconds with the cash and valuables. In his absence, Wiley leaves behind a message claiming going straight was too much for him and leaving the Castaways stranded once more.
- Norbert Wiley was played by comedian Don Rickles.
- Other shady characters on the island include Jackson Farrell, The Indigo Mob, The Ghost, Spy Gilligan and the Diamond Bandits.