Spy Gilligan was a Russian espionage agent known only as Agent 222 who has had plastic surgery to look like Gilligan. He carries a gold pocketknife with over 200 functions of which only a few are known, such as a tape recorder, radio transmitter, laser and the knife blade. (It's possible the "death ray" is the laser at a higher setting.) He has a certain amount on contempt for his superior, who he calls "commodant" and often response to with a "raspberry" or Bronx cheer. He sometimes regrets working in Russian intelligence and reconsiders becoming a doctor as per his mother's advice.
Following the cosmonauts landing on the island, Russian intelligence hires Agent 222 to land on the island and try to get intelligence on the Castaways's purpose on the island. Given plastic surgery to look like Gilligan and dressed like the First Mate, he studies Gilligan in covert footage and decides the easiest way to imitate Gilligan is by saying the first dumb things that come to mind. His mission as assigned by his commandant has four phases: Phase One - Arrival, Phase Two - Observe, Phase Three - Infiltrate and Phase Four - Reconnaissance. Stealing a pie and even taking the real Gilligan prisoner, his tactics only frustrate the others, annoying the Skipper and confusing Ginger by coming on to her. He stays in contact with his commander through his solid gold pocket knife with a two-way radio on it, getting pulled off the island when his cover is blown and nearly missing his boat on the way.
- The Spy was played by Bob Denver using split screen and a double in some scenes.
- It's possible Spy Gilligan appears on the island following information by The Ghost in the previous season.