Shikamaru's inherent nature is lazy, trouble-averse, and change-resistant.
He yearns for a peaceful life where he can watch clouds and do absolutely nothing.
Coupled with the influence of his father and his sensei Asuma, Shikamaru is a firm guardian of the status quo.
He believes in the system, even if he finds it annoying.
In the original timeline, during the Shikamaru Hiden novel, the antagonist questioned why ninjas should obey corrupt daimyos and wealthy merchants.
Why should powerful shinobi be dogs for weak civilians?
This is exactly the same question Makoto posed to Kurotsuchi.
The difference lies in the antagonist being a "frog at the bottom of a well."
He was unaware of the sheer power of Naruto and Sasuke, and he didn't understand the geopolitics of the Five Nations.
Plus, although his core question was valid, he used brainwashing genjutsu to enforce his will.
Shikamaru pointed out these flaws and defeated him.
This approach could convince most people, but it couldn't withstand careful scrutiny.
Because this wasn't a clash of ideologies at all—it was basically an internet argument.
When you can't win the debate on merit, you start digging through the other person's profile history.
You find something cringe, label them a "Genjutsu User" or a "Terrorist," and declare victory.
Since the antagonist used Genjutsu, and since he had personal ambitions, Shikamaru decided everything about him was wrong.
Using this black-and-white logic, his entire ideology was dismissed.
Take Nagato's original plan.
He didn't know about Kaguya.
He didn't know he was a pawn.
You could say his actions were extreme, but you couldn't prove his ideology (that pain brings peace) was logically incorrect.
It's as absurd as someone posting a screenshot on Reddit saying "The sun rises in the east." Then someone replies, "Lol, imagine believing a Reddit screenshot," and considers the argument won.
With Shikamaru's intelligence, he naturally understands the logical fallacies here.
But as mentioned before, he is a guardian of traditional rules.
He doesn't need to consider whether the enemy has a point. He just needs to maintain his own beliefs and protect Konoha.
This is why Makoto originally didn't approve of Shikamaru. He's smart, but his intelligence is conservative.
It differs from the revolutionary minds of Nagato, Mei, or Kurotsuchi.
'However..' Makoto decided to conduct an experiment.
Although he didn't know if it would work, he planned to try it on the lazy genius.
After all, Shikamaru came to him voluntarily. And this experiment wouldn't be bad for Shikamaru—it might actually fulfill his dream.
"You want to be an ordinary ninja," Makoto said, leaning back. "But you don't need to deliberately make yourself ordinary. If other ninjas are sufficiently excellent, you'll naturally blend in."
"Given your role as a strategist and your friendship with Naruto, I imagine you'd work hard to support him in becoming Hokage, right?"
"But that would run counter to your dream. Being the Hokage's right hand man is exhausting."
"However," Makoto leaned closer, "if Konoha learns a thing or two from the practices of Iwa and Kiri... you could achieve both goals."
"Decentralize power. Delegate. As long as there are enough outstanding individuals assisting the Hokage, your workload becomes infinitely lighter. You can go home at 5 PM."
Makoto's words were logical yet carried an absurdity that left Shikamaru perplexed.
Indeed, even if Konoha didn't overthrow the Daimyo, just decentralizing the Hokage's paperwork would be a massive reform.
And if other ninjas were capable enough... Shikamaru wouldn't have to carry the team.
There was another layer to Makoto's meaning: He wanted to take Hanabi to make her stronger.
This was a clear effort to enhance the abilities of "other ninjas."
In other words, if Shikamaru wanted to realize his dream of being lazy... the best approach was to let Makoto take Hanabi?
'What a drag,' Shikamaru thought. 'His logic is annoying because it makes sense.'
What puzzled Shikamaru the most was how Makoto, without a hint of sarcasm, straightforwardly believed that Naruto—the dead-last—could become Hokage.
Even among their friends, they thought Naruto's dream was a long shot.
"What else?" Shikamaru asked after a moment of thought.
"Whether you want a boy or a girl first—I can't help with that," Makoto shrugged. "Maybe seek out Orochimaru later. He's good with genetics."
"As for your desire to 'marry an ordinary woman' who is neither beautiful nor ugly... I can provide a case study."
"Oh?" Shikamaru's eyes lit up. "Please enlighten me."
This was a good thing.
The political stuff was heavy, but this? This was practical life advice.
Before coming here, Shikamaru had observed Makoto.
The guy was popular.
The Kage respected him. Women (scary ones) seemed to like him.
Makoto was qualified to teach this subject.
"Take your next match for example," Makoto said. "If.... If your opponent is Temari, the eldest princess of Sunagakure. She's three years older than you. She's strong. She's beautiful in a terrifying way."
"So, Shikamaru... what should you do to ensure she doesn't fall in love with you?"
"..."
Shikamaru was utterly bewildered.
What kind of strange question is this?
What did he mean by "ensure she doesn't fall in love"? Shikamaru wasn't Sasuke.
He wasn't some ultimate heartthrob.
He was just a lazy guy with a pineapple head.
'Hiss. Wait.'
Makoto had asked about "ensuring it doesn't happen"—meaning achieving a 100% guarantee.
Even the slightest possibility had to be eliminated.
'This is a probability problem,' Shikamaru realized.
He stroked his chin and lowered his head in deep thought.
In the end, he gave up.
His experience was too limited.
His father was henpecked and useless in this department.
"I really can't figure it out," Shikamaru admitted. "You tell me."
"Actually, I don't know either," Makoto said nonchalantly.
"?"
"What's the problem with that? Humans are complex creatures. Women are even more complicated. Whether you forfeit immediately, fight and lose, or defeat her instantly... any of these could attract attention. Reverse psychology is tricky."
"But..."
Makoto reached behind his back and pulled out a paperback book.
He shoved it into Shikamaru's arms.
"What's this?"
"This is the latest work by your village's own Kakashi Hatake. I got an advance copy through my connections. It seems to contain the answers you're looking for."
Makoto patted Shikamaru on the shoulder.
"Kakashi-sensei work?"
Title: "The Art of Seduction: How to Win Hearts (Or Avoid Them)." Author: Hatake Kakashi.
"You have less than twenty minutes left before your match," Makoto warned. "This is your final chance. Good luck—find the method in there. Master it quickly. It's time to test your intelligence."
After saying this, Makoto stood up and walked away.
Shikamaru wore a determined expression.
This was a mission!
He sat down, placed the book on his lap, opened to the first page, and began reading intently, his brain processing the text at high speed.
After reading for a while, Shikamaru suddenly scratched his head.
"Did I forget something?"
He looked around. "Oh right. Hinata's request... and Ino..."
"Forget it. Let the Hyuga clan worry about themselves. What a hassle."
He went back to reading.
...
Meanwhile, behind the seats, Ino was still unconscious, slumped against the concrete like a ragdoll.
'?: Hello? Anyone?'
...
Restroom Area.
Makoto walked into the restroom.
After coming out, he washed his hands and looked at his reflection in the mirror.
He fixed his hair.
"Oh," he muttered to himself. "I almost forgot."
Release.
...
In the Spectator Stand.
THUD.
Ino finally woke up as she jerked forward in her seat, gasping for air.
As soon as she came to, Ino stared at her hands in despair. Her face flushed a deep, burning crimson.
The Mind Body Switch Technique has a drawback: damage is reflected back on the user.
But it's not just pain.
It's sensation.
Touch.
Pressure.
Temperature.
She felt everything the host felt.
What had she just touched?!
She vividly remembered the sensation of washing hands in the restroom... and what happened before the washing.
"Damn you, Shikamaru!" she shrieked internally.
She looked over.
Shikamaru was sitting right there, absorbed in a book, completely ignoring her.
He hadn't even checked if she was alive!
Ino's anger boiled over. She had risked her life to help him, and this was the thanks she got?
Clenching her fists, Ino walked over, step by step, radiating killing intent.
"What book are you reading so intently?" she hissed. "Weren't you always sleeping during class?"
Curious before taking action, Ino glanced at the page Shikamaru was reading.
It was a page of jokes/anecdotes.
...
The Ino-Shika-Chō trio shared a dorm room.
They agreed to take turns turning off the lights.
One night, everyone was in bed, but the lights were still on.
Ino asked: "Whose turn is it? Why hasn't anyone done it?"
Chōji replied: "It's Shika's turn today."
"..."
Ino immediately recalled the sensation from the restroom a moment ago.
Her face turned from red to purple.
"DIE, SHIKAMARU!"
BAM!
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