Naruto charges Tsunade, Rasengen in hand, but his attempt to hit her is futile. She easily redirects his force to the ground. But she recognizes the technique that only Jiraiya and the Fourth have mastered. His isn't as powerful, but he assures her that he'll master it in three days. She then bets him - if he can master the technique in one week, she'll not only acknowledge that he can become Hokage, but will even give him her precious necklace. Shi*une thinks Tsunade has lost her mind! She's never offered that necklace in a bet before.
That night, Shi*une visits Naruto to explain the curse of Tsunade's necklace. There was one time when Tsunade was an upstanding medical nin in Konoha, but she lost all hope when her lover and brother were killed. That necklace symbolizes the two she lost. And Shi*une believes that if anyone other than Tsunade wears it, they'll die.
Meanwhile, Tsunade sits alone, holding her crystal, as memories of her brother flood her mind. On Nawaki's 12th birthday, she gave the necklace to him as a present. He happily accepted the necklace that their grandfather once possessed and vows that he will protect Konoha. One day, he will be Hokage. She removes his forehead protector and kisses his forehead. The next day he was killed in a raid.
In Konoha, Tsunade pursued her ambition to require a medical ninja on all four-person teams. She strongly believed this would drastically increase survival rates. But the counsel declined her request on the basis that Konoha was currently at war, and what she asks for would require great time and knowledge they don't have. And their enemy wouldn't wait. Only one nin stood up for her, a man named Dan, whose sister died that night in the raid. He asks to walk her home.
Tsunade then remembers the last day she saw her lover alive. He has felt so alone since his little sister died, but now his main goal is to protect the village. To become Hokage. Tsunade then gave him her necklace, but not long after, he died in battle. She arrived late and tried everything she could to save him, but he died in front of her.
Naruto is unimpressed with Shi*une's story and decides to train.
Meanwhile, Jiraiya and Tsunade drink together. He is amazed that Naruto got to her so badly that she bet him her necklace. She must know there's no way Naruto could master that technique in a week. And he inquires about Orochimaru's offer with a stern warning - if she dares to betray Konoha, he'll kill her. He knows she wasn't always like this. Once, she was concerned for the villagers as well. And Naruto must remind her of her brother - they're both the same age and recklace.
The next day, Jiraiya awakens to find Naruto still training, while Tsunade contemplates both offers she received.