Captain Bentley is the captain of the Lady Zay. Players help him remove the jinx from his ship during Lunar Diplomacy. He likes the "non-judgemental" attitude of the Moonclan people, stating their willingness to trade with them despite his crew killing and plundering. However, he is oblivious of the Moonclan having made the Cabin boy place a jinx on his ship, albeit unintentionally, making the crew sail in circles.
He can be found on the top deck of the Lady Zay and will be the player's point of contact if they wish to sail away from Lunar Isle to Pirates' Cove. He and his crew is not in any way affiliated with the Pirates in Mos Le'Harmless.
During Lunar Diplomacy, the player learns that he originally wanted to sail to Lunar Isle to plunder and kill off the inhabitants living there. But the threat of the Suqahs and the mind-reading powers of the Moonclan people deterred him from doing so. Bentley also reveals he was captain of a previous ship, but it was shipwrecked and only him and a few men survived. Those that couldn't escape the ship before it crashed and survived ended building the Pirates' Hideout. He wasn't directly involved in Monkey Madness, or The Grand Tree, however he did steal one of the warships from there, and transformed it into the Lady Zay.
- When the player asks the Captain Bentley about his ship named the Lady Zay, the player mentions that they used to own a ship named the Lady Lumbridge, which is a reference to the Dragon Slayer quest.
- Captain Bentley also tells the player that he stole his ship from the Karamjan shipyards, and that he doesn't know who they were building that kind of warships for, but whoever it was seemed to be a little on the short side. This is a reference to the quest The Grand Tree in which the Karamjan warships were built for gnomes.
- "Oh captain, my captain," is said by the player on the third time speaking to Captain Bentley. This is a reference to the poem O Captain! My Captain! by Walt Whitman.
- While talking to Captain Bentley, at one part his parrot says, "I want guns, lots of guns!", which is a quote from the movie, The Matrix.