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Hiruzen Sarutobi

The Third Hokage, grandfather of Konohamaru, and sensei of the Sannin.

Beware of the Nice Ones: He acts like a friendly grandfather figure, but in war he was feared as a God of Shinobi.
In Spite of a Nail: Because as Shikako points out, people don't survive using a suicide technique.
Old Master: Well past his prime and still indisputably S-class.
A Pupil of Mine Until He Turned to Evil: With Orochimaru.
Red Baron: Was known as a God of Shinobi.

Iruka Umino

An instructor in the Academy and a big brother figure to Naruto.

Big Brother Mentor: Is this to Naruto.
Friend to All Children: This trope is why he is a great teacher.
He Is All Grown Up: Non-romantic example with Naruto. He and Tsubaki are tracking Mizuki, Fujin, and Raijin, only to find that Team 7 (Naruto is a recent chunin) have already apprehended them.
Jack of All Trades: Iruka is competent at most ninja skills, as befits someone in charge of teaching them all, but specializes in nothing particular and is competent but no better.
Kicked Upstairs: Averted. Tsunade assures him that he will still continue teaching in the Academy, despite his promotion.
Rank Up: Promoted to special jounin for his contributions to Shikako and Sasuke's jounin project. Similar to Ebisu, his specialty is teaching.

Sakura Haruno

A friend of Shikako who didn't pass the final Genin test.

Anger Born of Worry: A rather selfish example. When somebody notices her practicing the Super-Strength technique and brings it up to Tsunade, who becomes interested. Sakura becomes terrified thinking the Hokage will be angry about jutsu theft until Shikako and Ino talk her down and remind her that training with Tsunade is a good thing.
Demoted to Extra: Downplayed. She's still not as active as the Leaf 12 since she's spending most of her time studying and working at the hospital, but she is still a recurring character who has important interactions with Shikako and has joined the kunoichi study group and recently began taking supplemental lessons from Tsunade herself.
Fangirl: For Sasuke. But she and Ino did not stop being friends because of it since Shikako presumably talked some sense into them. She still sighs over him and daydreams, but studying to become a field medic has absorbed all of her time and treating people who have been maimed and may die has helped her mature and better prioritize.
Healing Hands: Joins the Medic Corps to study medical ninjutsu.
Genius Ditz: She is smart, and may even be smarter than Shikako, but has less common sense and is more easily distracted by daydreams, etc.
Improvised Weapon: Sakura knocks out an escaped prisoner with a vase.
In Spite of a Nail: Even though she doesn't end up on Team 7, she still ends up become Tsunade's apprentice.
The Medic: Signs up for Medic Corps after failing genin exam, eventually becoming Tsunade's apprentice.
Muggle Best Friend: Downplayed. She's more of a Civilian Best Friend. She is this to Shikako and Ino even before she fails her team's test, having been raised by civilian parents and not getting certain aspects of ninja life.
Offscreen Moment of Awesome: When Tayuya breaks out of prison and goes for revenge, Sakura is the one to knock her out with a couple of glass vases. The girl with no field experience dropped one of Orochimaru's (admittedly weakened) personal guards. We actually get to see her do this in one of the Sunshine Sidestories.
- The events of Kiri Chunin Exams, since we only see her fight two times.
Rank Up: Promoted to chunin after the Kiri Exams.
Screw the Rules, I Have Connections!: Defied. She is best friends with the daughters of Konoha's former Head of Intelligence and current Jounin Commander but she never asks for favors from them nor blames them for her failing the genin test. The only time this is brought up is when Shikako offers to have an aunt sponsor Sakura to the Medic Corps program, and even then it's Sakura who convinces Igaku to sponsor her.
Super-Strength: Works on creating a version of this with Shikako, which gets her noticed by Tsunade. She later learns how to do this from Tsunade herself.

Ami

A classmate of Shikako and the others in the academy.

Alpha Bitch: In so far as a pre-teen can be one.
The Bus Came Back: Briefly in Chapter 81. Ami is in the Genin Corps running a small messenger bird post and reports to Shikako, Naruto, and Sai about the rumors near Kubisaki Pass.
Green-Eyed Monster: She hides it well, but Shikako notices that it is not pleasant for Ami to have failed the second genin test and then find out that Naruto has passed.
Jerk With Aheart Of Gold: Sort of... Ami is a jerk and we don't see her being nice, but she is responsible and dutiful, polite to people she doesn't like when they show up in her mother's shop, and won't let being mean get in the way of doing what she is supposed to do.
Reassigned to Antarctica: Subverted. Shikako realizes that despite how it looks, Ami's post is actually rather prestigious for a twelve-year-old Genin Corps member with only a few months of service under her belt. Being distant also means she is trusted alone and unsupervised, meaning the village acknowledges her as appropriately skilled and responsible.
What Happened to the Mouse?: Averted. After the graduation exam we never hear of her. In canon we kept never hearing her, while in Dreaming of Sunshine Shikako runs across her at a Genin Corps posting.

Asuma Sarutobi

The jounin instructor of Team 10

Armor-Piercing Question: After the Land of Moon mission he knocks his student out of his Heroic Safe Mode with one.
"You're a genius, Shikamaru. I think you could do anything you set your mind to. And that's the problem, isn't it?"
Generation Xerox: Defied, as Asuma is nothing like his father other than also being skilled and loyal.
Official Couple: With Kurenai.
Stealth Mentor: After having unconditionally supported Shikamaru before, he withdraws that support over a difficult subject to shock and provoke Shikamaru into supporting himself, and then returns to offering support once Shikamaru won't be using it as a crutch.

Kurenai Yuuhi

The jounin instructor of Team 8.

Easily Forgiven: It is uncertain how Yakumo feels about what Kurenai did, though they have both been present at the kunoichi study group without any fights breaking out.
Master of Illusion: One of Konoha's greatest genjutsu experts.
My Greatest Failure: Yakumo is hers, as she helped make the call to seal Yakumo's memories and abilities.
Official Couple: With Asuma.

Inoichi Yamanaka

The father of Ino and head of the Yamanaka clan.

10-Minute Retirement: Double-subverted. Inoichi is supposed to have permanently retired as the Head of Intelligence at some point in the past and, according to Anko in Sunshine Sidestories, says as much to people when they occasionally ask him to work a shift or look at a case. But then he will be talked into doing it all the same, because he is a patriot and the work is important.
Hidden Depths: This slightly goofy pretty-boy is not only a doting father, but a trained psychologist, deadly jounin Clan Head, and semi-retired Head of Intelligence, meaning he used to be in charge or the Torture and Interrogation division. Even being his daughter's closest friend, Shikako still feels uncomfortable if she thinks he's paying her too much attention.
Honor Before Reason: A rare positive example. With the discovery that Orochimaru's Curse Seals can be a Soul Jar and his own daughter's mental maiming by one, he has every legal and personal reason to Mind Rape Anko and find out everything he can as quickly as possible, even at risk to hurt her. Instead he tells her the situation, makes clear that she is his trusted comrade, and states that he wants to mind walk her to protect her as well, and would prefer her to agree instead of him having to get a warrant, and asks her to trust him. She does.
Mind Rape: With his family ninjutsu.
Off Screen Moment Of Awesome: He's one of the poeple who capture Hidan.

Konohamaru Sarutobi

The grandson of the Third Hokage.

Bratty Half-Pint: Because he's still in the Academy.
Fearless Fool: Shikako observes that his reaction to something that intimidates him is to reach out and poke it, as shown by his spending time with Naruto's friend Gaara. He still doesn't like Kankuro, though.
Girls Have Cooties: Averted, he is close friends with Moegi and can transform himself into a female form.
Green-Eyed Monster: Is jealous that Ranmaru is friends and was on a mission with Naruto.

Moegi

A friend of Konohamaru.

Tomboy with a Girly Streak: Played with. Moegi is loud, aggressive when offended, and close friends with two rowdy boys her age. She also boasts about growing up to be Konoha's sexiest kunoichi and is concerned with things like pretty clothes and nails. She also ardently looks up to Temari.
Values Dissonance: Two-fold regarding Moegi's background as the daughter of merchants. First, as a child of civilian parents, there are things about ninja life that she doesn't automatically know. Second, while her parents' status as prosperous merchants would be a social boost in civilian schools, in the Academy it gets her mocked with taunts of having bought her way through her classes.

Gai Maito

The jounin instructor of Team Gai.

Born Winner: Shikako notes that it was easy to label Gai as one of Konoha's rather ilustrious "dead-last" ninja who went on to excel, but the truth is that Gai was also a Child Prodigy. He made genin at seven, chunin at eleven, and has been Kakashi's rival as long as they've known each other.
Bunny-Ears Lawyer: Despite his fashion sense and obsession with "Youth!" Gai is an insanely capable Taijutsu master who can overpower and defeat even Kakashi.
Generation Xerox: Of his father, which he then passed onto Rock Lee.
Summon Magic: Has a Turtle summoning contract.

Ibiki Morino

The head of Konoha's T&I.

The Dreaded: The scarred and intimidating Head of Torture and Interrogation.
Hero with Bad Publicity: Well, he is a professional interrogator and he has a lot of things that he can do to or order done to people, but he mostly makes a point of seeming scarier than he really is. For instance, despite talking about torture implements, etc., he recognizes that it is an unreliable and ineffective practice and prefers to extract information through psychological intimidation and rapport-building between prisoners and interrogators.
Odd Friendship: With Shikako.
Pragmatic Villainy: So pragmatic that he recognizes that doing bad things is not useful or helpful. Despite being ostensibly in charge of torturing prisoners for information, he uses longer-term rapport building methods that don't harm them, and actively discourages other ninja from using torture to gain information, as seen when he questions Shikako about how she got marked as an interrogation specialist in Iwa's bingo book.
Reasonable Authority Figure: When Shikako gets an entry for interrogation in a Bingo book, he calmly asks and let her explain how that happened.
What Does She See in Him?: Non-romantic example with Shikako. All the other Special Jounin and Intelligence Division members are confused/horrified at how well Shikako gets along with Ibiki when they see her willingly seek him out, share tea with him, banter, and laugh at his jokes.

Anko Mitarashi

The former student of Orochimaru before he defected.

Amazon Brigade: Anko ends up as the jounin instructor of a team where all three students are kunoichi: Yakumo, Isaribi, and Sakura.
Ax-Crazy: Anko invokes this for psychological intimidation, but in actuality is relatively normal, if a bit extroverted.
Berserk Button: Orochimaru. The fact that he is still breathing upsets Anko so much that she considers Taking You with Me to be a desirable alternative.
- Subverted in regards to questions about her loyalty. It puts her in a foul temper, and random idiots who bring it up may be in danger, but when professionals like Inoichi raise concerns she acknowledges that it is a legitimate danger and will grit her teeth as she does the necessary tests.
A Day in the Limelight: Two of the Sunshine Sidestories are from her perspective.
Hidden Depths: A surprisingly good and caring teacher, particularly to her genin team.
The Mentor: She's acting as a guard, supervisor, and teacher to Yakumo and Isaribi and she seems to enjoy it. Also, regularly takes part in Kunoichi Club meetings.
- Ends up with her own genin team.
Rank Up: Promoted to full jounin sometime after Kiri Exams.
Reassigned to Antarctica: Downplayed, but after the discovery that Orochimaru's Curse Seal is a Soul Jar she is shuffled out of the Intelligence Division to limit her exposure to sensitive data. She considers her new posting to be a worthwhile commitment.

Jiraiya

One of the Sannin and the Toad Sage.

Beware the Silly Ones: Has an introductory poem and dance to proclaim himself a Super Pervert. Has been an S-class ninja longer than most serving ninja have been alive. Yeah.
Bunny-Ears Lawyer: Purposefully played up. Shikako notes that he is too loud and leering to be entirely serious in his perversions, despite there having to also be some truth to the rumors.
The Dreaded: His mere arrival scared off Kisame and Itachi. He leaks a little not-quite-murderous intent at Shikako when she annoys him as a reminder that his body count is higher than the number of days she's lived through.
Flash Step: In a Silver Queen approved one-shot, after Shikako is hit by Tsukuyomi, Jiraiya hears her screams and is immediately on the scene. Then he grabs the kids and dumps one-third of his chakra into a body flicker that gets them all back to Konoha, which was several days' walk away.
Geometric Magic: Potentially the greatest at it in the world. Jiraiya is the pre-eminent seal master, bar none, and Shikako has realized that he doesn't favor using Konoha's standard sealing style, but that it became Konoha's standard because he used it.
If It's You, It's Okay: A non-romantic example. Jiraiya swore to never take on any more students, and is only teaching Naruto due to his responsibilities, but Shikako's sealing notes and projects show so much raw potential that he begins feeding her tidbits of lore and advice despite his past losses.
My Greatest Failure: Thus far he believes himself to have outlived every one of his many students and swore to not take on anymore.
My Greatest Second Chance: Sees teaching Naruto as this. He may act as The Mentor to Shikako because of this as well.
Number Two: When he's in the village he is this for Tsunade. Jiraiya is the one is charge of finding who let the surviving Sound 4 out of prison, etc.
Summon Magic: With toads, as the Toad Sage. We see several toads that weren't used in canon, such as toads for prisoner transport or body-guarding.

Tsunade

One of the Sannin and the Fifth Hokage.

Berserk Button: A low-key one, but she doesn't like people interfering with her hospital.
A Day in the Limelight: Multiple chapters of Sunshine Sidestories are from her perspective.
Healing Hands: The best in the world. She has specifically saved Shikako's life at least twice, once reviving her despite Shikako's 100% depleted chakra, lack of pulse, lack of breathing, and uncertain neural activity.
I Need a Freaking Drink: Tsunade likely qualifies as a functioning or former alcoholic. This is also her reaction to Kakashi's blaming Zabuza for Shikako's monologue, and Zabuza's counter-bantering. She describes the world as tilting 45 degrees to the side and actually checks her (zero-proof) drink to ensure that she is not, in fact, drunk.
The Mentor: To Sakura.
My God, What Have I Done?: We see her thoughts when Naruto brings back Ibiki partway through the Sound Retrieval Mission. For the few minutes she spends believing they are the only survivors, she hates herself exactly as much as you would expect given her belief that she just sent 6 twelve-year-old children to their deaths, and knows that she couldn't have safely made a different decision, either.
Politeness Judo: Perfectly capable of doing this as shown during various Chunin Exams.
Properly Paranoid:
- She knows that something is rotten in Konoha and doesn't know who it is that is subverting her orders and passing along information to their enemies. She needs a lot of safeguards and plans and safety-measures to figure it out.
- She forbids Shikako and Sasuke from ever talking about what really happened in Land of Hot Springs, since people would either blame Konoha or try to repeat it.
Reasonable Authority Figure: She has extended a shockingly large amount of trust, leeway, and forgiveness to Shikako for her unconventional actions, partly due to her friendship with Naruto and partly due to Shikako's shocking success rate. For instance, she allows a supervised Shikako to access Orochimaru's old jutsu notes.
Super-Strength: Yes. Despite her usual portrayal, in dreaming she yells a bit but has not been shown to vent her temper through violence. She is teaching this to Sakura in their spare time.
- Finally shown in action when fighting Isobu - despite standing on water, she manages to drag him back and throw him a considerable distance away.
Summon Magic: Signed the Slug contract.

Chiyako Aburame

Shino's little sister.

Cool Big Bro: Chiyako sees Shino as this.
Giver of Lame Names: Averted. Mr. Cranberry is a perfectly respectable and creative name for a red-kneed tarantula.
Kids Are Cruel: Chiyako was invited to a slumber party, but then the other girls revoked the invitation, called her names, potentially assaulted her (it isn't mentioned how she got her twisted ankle), and smooshed her pet spider (he survived, though).

Hanabi Hyuuga

Hinata's little sister.

Bratty Half-Pint: Subverted. Hanabi is disconcerting to some people because she speaks with authority and has been raised to command, but she was also raised in a house with strict adherence to etiquette and does not speak improperly to people above in in society.
What Is This Thing You Call "Love"?: In Hanabi's case, it's more What Is This Thing You Call Friendship? Her growing connection with Chiyako and Moegi has aspects of this, having never particularly had peers or teammates she was close to in the past.

Tsume Inuzuka

Kiba's mother and head both the Sensory Squad and Tracking Team.

Action Mom: Single mother of two children. Also an active duty ninja, a clan head, and leader of both the Tracking Team and the Sensory Squad. She also runs the Inuzuka Clinic.
Amazingly Embarrassing Parents: She apparently spends way too much time talking up her children to potential spouses—even though Kiba is just thirteen.
Giver of Lame Names: Kiba's older sister wants people to think that her name uses the "flower" kanji, but actually Tsume was on the good drugs at the time and used the "nose" kanji instead.
Mother Bear: To Kiba and Hana.
Parents as People: Inverted? Defied? Whatever it is, Tsume manages to be a doting and well-loved single mother to two children despite all the responsibilities listed under her badass entry. Shikako can't imagine how she finds the time.
Reasonable Authority Figure: She makes Shikako explain herself about rushing into a fight without waiting for orders before deciding whether to keep yelling at her for it. Earlier she took the time to test Rock Lee's sensory perception at his request despite having no super-sensory skill, and complemented him on having solid chunin-level perceptiveness.
Shipper on Deck: Hints to Shikako that she wouldn't mind seeing her and Kiba together, since their kids might actually inherit some brains. May also be her being a Troll who wanted to spark Shikako's reaction for kicks. Or both.
Sitcom Arch-Nemesis: Has this relationship with the head of research and Development, as seen when she drags Tsunade in to arbitrate which of their divisions can recruit Shikako.

Yakumo Kurama

The last member of the Kurama clan.

Art Initiates Life: Subverted. She paints things to activate her powers, but instead of summoning monsters she paints natural disasters that materialize, and they are only illusions.
Birds of a Feather: She admires Rock Lee because, like her, he can only use one ninja art and is dedicated to becoming a great shinobi with a limited toolkit. In turn, Lee admires Yakumo’s dedication just as much.
Blue Screen Of Death: Enters this after her alter-ego breaks loose during a spar with Shikako and she remembers killing her own parents. Anko mercifully knocks her unconscious before she can break worse or hurt someone else.
Broken Bird: Snapped under the stress of her clan's expectations, repressed the memories of murdering her parents and became paranoid that they were assassinated by the Hokage, had her powers sealed, and was placed under house-arrest with 24/7 guards and no peer contact for several years.
Elemental Powers: Subverted. Yakumo mostly manifests attacks as fires or strikes of lightning but these are both just manifestations of her illusions.
Master of Illusion: Her skill specialty. Due to ill health, it is just about her only ninja skill. She's powerful enough to cast one over the village that can temporarily fool even the skilled join.
Master of One Magic: Of the three main ninja arts, she can only do genjutsu, but she's exceptional at it.
Self-Made Orphan: Due to her alter-ego setting a fire that killed her parents.
Superpowered Evil Side: Her bloodline is prone to these due to their Reality Warping abilities
Word of God: Yakumo and Lee have agreed that they will form a team with a person who can only use ninjutsu if they ever meet one.

Genma Shiranui

A special jounin of the Hidden Leaf Village.

Born Unlucky: Wonders if he's this because of how often he has to patrol with Sasuke and all the stuff that happens then. The truth is that at least one of his special jounin friends has been rigging the straw drawing that decides who watches Sasuke.
Stating the Obvious: Points out that everyone knows who Hayate is dating and that she's an Anbu captain.
Weirdness Magnet: Hates working with Sasuke because he is this. In Sunshine Sidestories he claims some of their patrols' happenings have given him nightmares.

Aoba Yamashiro

A special jounin of the Hidden Leaf Village.

Cool and Unusual Punishment: He did none of Shikako's paperwork while she was gone in revenge for siccing Gai on them, but she didn't care.
Cruel and Unusual Death: Is ritually sacrificed to Jashin in an effort to summon the kami.
Killed Off for Real: He was the penultimate sacrifice of the Cult of Jashin.
Troll: Tries to do this and just leaves himself open to Shikako's more devious trolling.
Unfazed Everyman: Thought he could be this, but Team Seven's luck was just too much. Now he's beginning to become jaded.

Shiho

An member of the Intelligence Division who specializes in decoding.

Action Girl: Defied. Despite being a kunoichi, Shiho considers herself very much a desk-worker, does not ever expect to enter the field, does not want to, and wishes she could skip her 4 hours of Operational Readiness each week.
Cool and Unusual Punishment: Treats her required four hours of physical work-out time each week as this, although not training alone makes it more enjoyable.
Ditzy Genius: Very high IQ and coding/deciphering skills, but rather empty-headed about many other things.
Friendless Background: Recruited directly out of the Academy according to canon, and she doesn't know much of anyone other then her co-workers, especially not of her age group.

ANBU

In General

The ANBU are Elite Mooks who are directly chosen by the Hokage. They report directly to the Hokage and are tasked with high-level missions.

Cool Mask: All members wear one when on active duty to hide their identity.
Undying Loyalty: To the Hokage.

Kisuke Maboroshi

A member of the ANBU who serves even as a ghost.

Posthumous Character: We meet him months or years after his death, as a ghost.
Soul Jar: The seal that his soul is tied to. In a twist, this seal is also what killed him first, as it yanked his soul out of his body against his will.
Undying Loyalty: Even though he is dead, he still wants to serve the village instead of continuing to the afterlife.

Tenzou

A member of the ANBU and a friend of Kakashi.

Break His Heart to Save Him: In this case, it's more Get Him Fired To Save Him. Tenzou got Kakashi invalidated out of ANBU for his own good, and Kakashi was bitterly angry.
Early-Bird Cameo: Shikako meets Tenzou about two years early when Kakashi recruits him to help with her sensory training.
Easily Forgiven: Double Subverted. Kakashi was furious at the perceived betrayal of Tenzou getting him kicked out of the Black Ops, but Kakashi's life has since turned around enough to have almost entirely forgiven Tenzou.
Green Thumb: Per canon, with his mokuton.
Outside-Context Problem: Kakashi has Tenzou unknowingly invoke this on Shikako. She's training her senses and reflexes by trying to sense Kakashi sneaking up on her, and after he's almost finished with the lesson Kakashi predicts that she's gotten into the bad habit of only scanning for his chakra and has Tenzou sneak up on her instead.
Spell My Name With An S: In his introductory chapter in Dreaming, Shikako's dialogue and narration spells his name Tenzo, but in his point-of-view chapter in Sunshine Sidestories he spells his name Tenzou.
Stealth Hi/Bye: Shikako meets Tenzou when he sneaks up on her unnoticed in broad daylight in the middle of a room full of other ninja.
Supernatural Sensitivity: Apparently is rather skilled chakra sensor, even being able to sense natural energy.
What the Hell, Hero?: Gives a low-key one to Kakashi for not telling him that his Sharingan chakra exhaustion was cured.

ROOT

In General

A secret division of the ANBU who are more loyal to Danzo.

Cool Mask: Members of ROOT wear masks that have the kanji for "root" on it.
Undying Loyalty: To Danzo instead of the Hokage.

Danzo Shimura

A friend of the Third Hokage and one of the village elders.

The Corrupter: Shikako has noted that Orochimaru, Kabuto, and Itachi all took turns for the worse in different ways after their entry into Root.
The Dreaded: Among people who know much of anything about him. Shikako is secretly an exaggerated example because she knows so much that she is all-but paralyzed by terror when confronted with his presence.
Geometric Magic: Danzo may or may not have designed it himself, but when Shikako looks briefly at Sai's silencing seal she identifies it as being very complicated and possibly using multiple concepts expressed and overlapping at once.
Nice Job Fixing It, Villain:
- By assigning Sai to spy on Naruto and Shikako, he gives her an opportunity to the boy into The Mole.
- By forcing Shikako, Shikamaru, and Naruto to immediately report and arranging for Tsunade to not be present despite her prior orders and the usual code of conduct for returning ninja with injuries, when Shikako collapses and almost dies from her wounds during the debrief Tsunade has the right to charge the elder council with negligence in their duties and sharply curtail their influence.
- When he reports to Tsunade that Shikako disappeared from hospital and blames Kumo for this. Since Shikako just finished her own report, Tsunade knows it's not true and goes to investigate everything personally.
Straw Misogynist: Downplayed, but in Sunshine Sidestories he tells Sai that kunoichi always have soft hearts and rarely make good ninja. He also refers to Tsunade as "that woman".
Throw the Dog a Bone: Subverted. Danzo praises Sai for making bonds with Naruto and Shikako, which is a rare and fleeting event. However, Sai mentally adds that praise is often the only reward offered for a mission completed beyond expectations, and wishes he hadn't been praised at all.
Villain with Good Publicity: Even once Jiraiya has shown Tsunade evidence that Root is active despite being disbanded and may be committing further treason, her reaction is to think it unlikely that Danzo was responsible. Justified, because Danzo is a respected war hero and trusted comrade of the Third Hokage.
Tsunade: I never liked him, but ... treason? That's not Danzo. Always, his focus has been on making Konoha stronger. (mentally) 'It might not be Danzo though, just the continuation of his secret Black Ops group.'
- If this seems like an Idiot Ball from Tsunade, there's Fridge Horror in the thought that Danzo might have already used his undetectable mind-control genjutsu on her.

Sai

A member of Root who occasionally spies on Shikako on Danzo's orders.

Big Damn Heroes: Smuggles Shikako out of hospital and to Tsunade before Danzo can kidnap her following the Hot Springs Arc.
Character Development: Originally Sai is exactly as serious, emotionally repressed, and mentally inflexible as one would expect. After a few missions of exposure to Naruto and Shikako he informs them of his secondary set of orders and shows them his seal. In the Land of Moon, he subverts Shikako's direct orders out of concern for her well-being and then implicitly promises to keep her secrets out of his report to Danzo.
Do Well, But Not Perfect: Averted and Lampshaded. Shikako notices his shinobi ID looks brand new despite supposedly being several years old, hinting it's a fake.
Early-Bird Cameo: Originally a Shippuden character, Naruto and Shikako go on several missions with him prior to Naruto's training journey.
Literal Genie: Becomes this when Naruto and Shikako have gotten through to him a bit. He follows Danzo’s orders—and the mission leader’s—to the letter. For example, Danzo told him to report everything he saw with his own eyes, and Shikako (while in command) told him to remain behind while she attacked an enemy. So, therefore, he sends an Ink Clone to watch Shikako during her one-ninja assault (just in case), and later neglects to report some of the things she tells him (which, technically, wasn't something he "saw") to Danzo.
The Mole: Danzo has him assigned to Naruto's team for several missions to spy on Naruto. Shikako is in the process of turning his loyalties more toward herself and her friends.
Real Men Wear Pink: Besides his canon love of painting, he has tentatively begun transcribing Shikako's retelling of Sailor Moon into manga format. Shikako finds the idea of forcing Danzo to read about school-girl soldiers of Love and Justice when he reviews Sai's records hilarious.

Characters / Dreaming Of Sunshine Hidden Leaf

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