Ishidate

Ishidate is missing-nin that was hired by Shabadaba to kill Michiru Tsuki and his son Hikaru Tsuki. Ishidate was hired by Moon Country minister Shabadaba to help in overthrowing the current king Kakeru Tsuki. He used a unique gauntlet to assassinate Kakeru Tsuki. He was first seen as he witnessed Konoha's ninja arrival of the fortress, and escaped with ninja techniques. Ishidate made a presumption that his team was stronger than Naruto Uzumaki's. He then comes again to stop Michiru and the team to go get help from other lands. There he battles Kakashi Hatake and, with the assistance of his performance dulling gas, easily outmaneuvered Kakashi and ultimately petrifies Kakashi's arm. He even petrified Korega and sliced him into many pieces. After Naruto used the power of the Nine-Tailed Fox, Ishidate decides it better to retreat as his team had already captured Michiru.

Later when Naruto's team, along with the circus people and Land of Moon soldiers infiltrated the palace, Ishidate and him men were ordered to stop them. He petrifies a soldier and tries to kill Hikaru. Naruto manages to stop him from doing so, and uses the Nine-Tailed Fox power once again. Naruto then uses the Multiple Shadow Clone Technique to overwhelm Ishidate was stomped on the clones of Naruto many times. He was implied dead, but was still alive and he petrifies Naruto's leg. Ishidate then plans to kill Naruto and Hikaru, but Shabadaba tells him to kill Michiru. Getting annoyed, he unwitting petrifies Shabadaba. Seeing bigger problems ahead of him, he picks up stones, and turns into multiple sharp rocks and fires at Michiru. After scoring some hits, Ishidate seems to prepare more of a final jutsu, but was immediately stopped by Kiki (monkey) and Chamu (saber-tooth tiger). Ishidate then tries to get them off, and he does. However they buy enough time for Michiru, whose carrying Naruto on his shoulders and helped along by his son Hikaru, to gain momentum and charge toward him. By the time Ishidate has gotten the animals off him, he hit point blank by Naruto's Crescent Moon Rasengan, blasting the section he on into smithereens and taking him out for good. His fate afterward is unknown, though he is presumably dead or incarcerated.

Personality
Immediately upon his introduction, Ishidate showed himself as an arrogant and egotistical man. He has a tremendous amount of confidence in his abilities; so much so that even when knowing he was up against one of Konoha's best ninja, Kakashi, he already believed himself to be the superior. Despite his arrogant nature, he has shown himself to be an intelligent man. While Kakashi was launching a powerful assault on the main gate, Ishidate deduced that it was a diversion tactic and had his men find Kakashi's teammates. Ishidate's arrogance seems to come from a superiority-complex as seen during his second battle against Naruto. When Naruto managed to defeat him (albeit with several clones and demon fox-enhanced might) Ishidate completely lost his composure and became deranged, completed obsessed with killing Naruto to reaffirm his belief in his abilities despite being giving orders to kill Michiru first.

Abilities
Like the rest of his team, Ishidate's primary battle tactic is close-range taijutsu while utilizing a powerful and odorless performance dulling gas to weaken his opponent's senses and reaction time, thus making it easier to fight. In addition, he possesses a unique gauntlet which allowed him to control stone and petrify any living material he touched.

Trivia

 * Like the rest of his team, Ishidate's appearance seems to be like Jiraiya based off kabuki actors.
 * Ishidate is seen wearing a wig, like Karenbana does, and Kongou too.