Be happy with sports - Chapter 24 The First Christmas After Return 1

Some say reincarnation is a blessing, but for me, it's a dreadful curse. Cursed with endless reincarnation, I've been reborn as a villain 137 times. And all 137 times, I've been toyed with and killed by heroes who are far more cruel than the said villains... If I can't win no matter what I do, then I'll crush those so-called heroes at their very roots. - Quality Fan Translations, Made by Fans for the Fans - Villain Takes Over The Academy

The first time they met they had battled fiercely, just for a mere bunch of herbs. She needed it to save people, and he wanted to use it to save his own life.

After Reincarnating into Naruto World at the Warring State Era as an Uzumaki, Masahiko thought that he got a useless System. He lived for 48 years as a normal, below average Uzumaki Shinobi.

That changed when he finally knew how the system works the day of his 49th Birthday!

- Description from Novelupdates

Nagasawa crossed to Naruto Universe and was bound to Konohagakure.If Konoha is severely damaged and destroyed, Nagasawa’s lifespan will be reduced.He panicked at the thought of the upcoming Nine-Tailed Demon Fox's attack , and the thought of Konoha getting destroyed left him in despair.Fortunately, while bound to Konoha, he can obtain templates of powerful characters.At the beginning, He got the Whitebeard template! Since it's the Whitebeard from the Summit War of Marineford, he can use Tremor-Tremor Fruit's ability and Haki.Facing the Tailed Beast Ball, which terrorized Konoha Shinobi, Nagasawa leaped and shattered the Tailed Beast Ball with one punch!