The Skipper served in the Navy and fought in WWII in the South Pacific, earning the rank of Captain. He led the navy band for 5 years aboard his ship, and was the best poker player in all of the 7th fleet.

The Skipper met Gilligan in the navy, where Gilligan saved his life by pushing him out of the way of a depth charge that had broken loose and was rolling down the deck of their destroyer.

After retiring, the Skipper used his commission to buy the S.S. Minnow and began offering 3 hour tours from Honolulu harbor. Gilligan was his first mate.

The Skipper has the heartiest appetite. He played the line on the high school football team, and now weighs in at 220 pounds in his mid-forties. He says if they ever get rescued, "I'll go straight to an Italian restaurant and have 8 or 10 pizzas, 6 dozen meatballs, and 2 miles of spaghetti, and then I'll have dinner." His favorite steak sandwich? A filet between two top sirloins!

He is also superstitious. The Skipper has witnessed a number of peculiar happenings with some tribal natives. He's always worried about voodoo curses and is constantly warning Gilligan to be on guard. Typically he then falls prey to them himself.

The Skipper is the castaway's good-natured leader. He is brave and sure, and is always looking out for them - particularly Gilligan. He continually encourages the castaways to work together toward what he knows will be their eventual rescue.