Gilligan practices golfing instead of working. Gilligan and Skipper are building a watch tower. The Skipper had a dream that a boat passed by the island. This is the third night in a row that he's had the same dream. Gilligan accidently hits Skipper with the golf club on his backswing.
Thurston is playing golf. Gilligan walks by carrying some supplies for the watch tower. He putts the ball at Thurston's insistence with the ball going in the hole. Gilligan does it again and the ball goes in even while Thurston is talking. Thurston decides to bet money that Gilligan can't do it again but Gilligan only has a quarter to his name. He does it again and again and again, each time Thurston bets double or nothing. It's night and they're still there. Skipper comes by very angry because Gilligan hasn't been working. He tries to talk Gilligan out of gambling but is shocked when Gilligan mentions that he's already won three million dollars.
The other castaways can't believe Gilligan's luck. Everyone starts being nice to him. Skipper gives him some advice. Skipper goes to track down Thurston to make sure that he pays his debt. Once Skipper is gone Thurston comes in. He makes Gilligan fill out an income tax form. Thurston decides to give Gilligan an oil company in exchange for his three million dollars. The oil company is a worthless white elephant. The other castaways can't believe Thurston's trickery toward Gilligan. But when Thurston turns on the radio only to hear that the oil company that Gilligan now owns has struck oil.
Gilligan writes a list of presents that he wants to give to the other castaways. Skipper orders Gilligan not the let anyone in the hut because he thinks that they are going to try and take advantage of him. Ginger tries to romance him. While Thurston tries to enter but Skipper catches him.
Gilligan and Skipper go to dinner at the Howells. Thurston tries to win back his money offering the Skipper all sort of games. Skipper mentions that he only bets on pool. Thurston unveils a pool table. Thurston is quite a hustler as Skipper doesn't even get a chance to play. They've played all night. Skipper owes Thurston $12 million. They give Thurston back his oil company.
While listening to the radio everyone finds out that the oil strike was from a buried oil truck. The land is still worthless. Thurston faints upon hearing the news.