Jack Ronald Arlington (or Pepper Jack, as he used to be known in his pirating days) is the captain of the Morning Star, a ship that sails around northern Andamar. Arlington is known for his love of adventure and his sense of humor (which tends to exasperate non-sailors). He is well-liked by his crew and the people on Andamar's eastern coast. He’s sailed for at least fifteen of his fifty years, and knows the seas well, although he knows that there’s plenty out there that he’s never seen. Still, most rookie sailors feel honored to serve with him.

His ship is crewed by men he calls the Heartbreakers (although visually, none of them are): Armand, Arnold, Arthur, Archibald, Barney, Bart, Bernard, Carl, Carter, Edgar, Edward, Garth, Harvey, Lars, Mark, Mario, Omar, Oscar, Richard, and Bob (the carrrpenter).

J.R. as he's now known, sails to Utopia Island often, although he'll charter his ship anywhere if the price is right and the passengers can put up with his sense of humor. He puts the piratical rolled r into every word that has the ar sound, especially his own name, which he pronounces Arrrlington. In fact, he chose his crew members partly on the basis of their names (or their occupation, as is the case with Bob). His favorite meal is quarrrtered arrrtichoke hearrrts in tarrrtarrr sauce.

There are four things he likes more than anything: a good laugh, a good ship, good treasure and a good drink. Those who travel with him are assured of this and more.

J.R. has since traded in the Morning Star for the legendary ship the Pale Moon, which he is now the captain of.

Since his Wish was granted, J.R. is now 45.