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The father of the three Kagestu children and owner of the land of the Kagestu estate. He fakes his death to trick his family.
Tobei Kagestu is a wealthy land owner who has profitted massively from the herbs that grow on and around his property on the mountains in Motoyoshi Village. The herbs are a valuable medicine and have helped turn Tobei and his family from a poor family unit to a rich estate that could honestly be set for life. However, he dies a while after the estate becomes rich and plans to leave it all to his eldest son Futa onthe condition that during his funeral procession, he does not laugh. If he does, then the estate is divided up amongst his relatives and Futa gets nothing.
In truth, Tobei is not dead and alive and well. What happened was that he and his youngest daughter Mai, who he lived alone with, faked his death and the funeral in order to get his family together and laugh again. Through a flashback, we see the Kagestu family of Futa, Tsukiko, mai, and Tobei sitting around a table laughing and having a good time despite being poor and that all changed when they found that the heras could be sold for high profits. The plan was that he would disguise himself as an old woman who Naruto and Shino meet and put the laughter clause in his will. If no one would laugh, then Mai would spike everyones drinks with a Laughing Poison that Tobei tested on Shino first.
After all of the events of the episode, the Kagestu family is back together smiling and Tobei gives Shino a sample of the poison to take back to the Hidden Leaf Village.