Jolene

Jolene is a woman who acts and dresses like a pirate in The Legend of Zelda: Phantom Hourglass. She has a strong hatred of Linebeck due to an incident from when they were young, and travels the sea trying to hunt him down. She has a sister named Joanne who likes to dress as a mermaid; a line of dialog from Joanne indicates Jolene also has a mermaid costume, but never wears it. She uses a scimitar in battle, and her appearance and battle tactics are extremely similar to the Gerudo Thieves in The Legend of Zelda: Ocarina of Time, likely inspired by their pirate counterparts in The Legend of Zelda: Majora's Mask.

Jolene first appears on the sea after Link has beaten the Temple of Courage. Linebeck rushes through an explanation of who she is and warns that her ship fires torpedoes. These torpedoes quickly move along the surface of the water, tracking the SS Linebeck's position, and can only be avoided by jumping at the right time. The torpedoes will not only damage the ship, but slow it down, allowing her to get closer. With good jumping, she can be outrun as her ship otherwise moves slower than Linebeck's, or he can use a cyclone to warp, travel to another sea, or land on an island. Her pursuit will pause if Link uses the Salvage Arm, fishing pole, or boards another ship, but will resume once that is over.

If she successfully boards the ship, Linebeck will hide in a crate in the engine room while Link must battle her. To attack, she swings her sword rapidly, and can also do a forward slashing charge attack with it. She will also parry Link's own blows and leap backwards away from him. To hit her, Link must attack her back after one of her charging attacks. After three enough hits, the two will lock blades and the player must rapidly rub the stylus back and forth across the screen, eventually pushing the sword from her hands. Once disarmed, she admits defeat, though makes it clear she is not giving up yet and is now angry at Link as well. She then leaves, allowing the two to continue on.

Following the first time she is met, Link receives a letter from her through the Postman, though the letter is actually intended for Joanne. Link can deliver it to Joanne for a reward. For most of the rest of the game, Jolene can be seen on the map patrolling a specific route around whichever sea she is in, trying to find Linebeck. Usually, she arrives at the specific sea around the same time as Beedle. Since she is so persistent, the battle against her can be done as often or as little as the player wishes. Upon giving the three pure metals to Zauz, they receive another, threatening letter from Jolene, acknowledging her defeat by Link (whom she refers to as "boy in green") and demanding a rematch as revenge. While Linebeck tries to persuade Link to not listen to her "ranting and raving," Link decides to face her in battle again to give Zauz some time, and Linebeck reluctantly agrees, admitting it might make the seas safer.

When Link next meets Jolene, she tells him she knows all about his quest to defeat Bellum using the Phantom Sword. She also addresses the "wooden box" where Linebeck is hiding, telling both that Link's attempts to defeat it will only result in his own death. She adds that if Link really has no regard for his own safety, he should face her, as she has finally "perfected the art of pirate fencing." A battle ensues again, but this time once disarmed, she picks up her sword again, saying the battle is not over. One more successful hit against her causes her to drop her sword again. She runs to the stairway, telling Link he is still strong, but that she still believes he is crazy for what he is attempting. However, she also says she finds his stubbornness intriguing, saying that the look she sees in his eyes is the same as "the one who captivated [her] long ago," unsubtly referring to Linebeck himself. She then tells him to tell "the man in the crate" to take some notes, as he may learn something from Link. She turns around, angrily calls Linebeck a fool, and leaves one last time.

Ciela then asks Linebeck about his history with her, and he tells them he met her when he once slammed his ship into a monster at sea while trying to escape from it, having lost control of the boat. They then traveled together for a while, though their differences in personality caused them to drift apart, as she was much tougher than him, who did not consider himself up for the "rough and tumble" pirate life. He reveals he has always preferred to sneak away with treasure, which he finds more laid-back, and due to him and Jolene seeing each other increasingly less often, decided to end their relationship by doing just that to her. After Ciela scolds him, Linebeck also notes in an amused tone that the treasure itself he took was not particularly great, and that he did not realize it would anger her to the point of getting her to spend years trying to hunt him down.

In the manga adaptation, her role is essentially the same, though her and Linebeck's backstory is expanded upon, revealing the treasure Linebeck stole from her was an octopus.