At Wit's End

Summary: Shikamaru is valued for his intelligence. But what if he no longer had that? While on a mission, Shikamaru is rendered a silly, playful moron. With the mission and everyone in danger, can his friends find a way to get him to do what he does best?

Disclaimer: I do not own Naruto, Boruto or its characters. This is a fan fiction written by me for fun. No profit is being made. Naruto, Boruto and its characters belong to Masashi Kishimoto and Mikio Ikemoto.

Chapter 1:

"You want me to what?" Shikamaru asked, suppressing a yawn.

He had been called before the Hokage before the sun had even risen. He had been up late last night assisting the older shinobi with projects in the village and played shogi against himself to wind down. None of the projects they had him work on were very difficult but they were tedious. He had been hoping to sleep in today.

Kakashi looked at him from across his desk. "We got a new mission and your name was the first one I thought of."

"Lucky me," Shikamaru mumbled sarcastically.

"This mission is perfect for you. And not just because they specifically requested you."

Intrigued, Shikamaru raised his brow. "A specific request?"

"Well, it's not like they know you by name, but the description is all you." Kakashi seemed amused when he said this, leading Shikamaru to wonder if this was an elaborate joke at his expense or something embarrassing. He was afraid to ask for the mission details.

The last time Kakashi had this look on his half-hidden face, it was because he had canceled a mission to go on a date with Temari. The look of utter delight in Kakashi's eyes still filled him with embarrassment.

Kakashi held up the paper. "A village requested us to send our most intelligent shinobi for this mission. Your name was the first one I thought of."

"As flattering as that may be, I doubt I'm the most intelligent," Shikamaru said matter-of-factly. "A village this size? And something that's so ambiguously measured? Are we talking experience? Book smarts? Come on, Kakashi…"

Kakashi wasn't the least bit dejected. "I won't bore you with the details, but the description of what they were looking for seems right up your alley." Kakashi glanced at the paper in his hand. "They want someone who's clever, good with puzzles, problem-solving and strategy skills. Now you tell me that doesn't sound like you."

Shikamaru had no retort, though he did have a question. "Why do they want someone like that specifically?"

Putting the paper on his desk, Kakashi said, "It seems this village is under threat financially. A more lucrative town lent them a hand, along with other small villages. They're all affiliated with each other. My understanding of this deal is that the town helps take care of the villages, sending them supplies, tools and other types of assistance in exchange for taxes."

"Because they're affiliated with the town and they're just a village."

"Recently, the town increased their taxes and they can no longer afford to pay them."

"Hench the financial problem."

Kakashi nodded his head. "They opted out of their agreement, but the town wants them to pay back all the aid they had been given over the years which is even more than the taxes. They can't afford it and, without the town's help, they don't have access to certain things anymore. They only became stable with the town's help. If they have to return everything they had been given or pay this exorbitant amount of money for their assistance, they'll be bankrupt and the villagers will have to leave their homes."

"Pretty impossible position they put the villagers in," said Shikamaru. "Either they return all the equipment that helped them reach stability or they pay to keep all that they had been given, both of which they can't afford to do."

"Which brings us to the mission," Kakashi continued. "The town's leader offered them a deal. If they can pass his test, he will forgive the debt and leave them in peace. He said they had to appoint one person to take the test publicly, but it could be anyone they wanted. Even someone outside their village."

Shikamaru raised his brow again. "Meaning they could call on aid from a shinobi village and have one of us take the test for them."

"The only condition was that they could not ask the town's leader to take the test because he knows the answers. Otherwise, anyone can take the test. Apparently, it has nothing to do with local knowledge or anything personal about anyone. The town's leader said it was to see how clever they were."

Lowering his head in thought, Shikamaru's mind began to make connections. "I see. So, it's possible that this is more of a riddle than an actual test."

"No one knows what will be asked, but it's a fair assumption," said Kakashi. "Since you're good with puzzles and an excellent strategist, I can't think of anyone better for this mission."

"Maybe, but you also see the issue, right?" Shikamaru asked Kakashi, certain he hadn't overlooked the obvious. "They made a point of saying that they could pick anyone, even someone outside the village to take the test. Meaning the possibility of them calling for shinobi assistance did cross their mind. They're probably prepared for that."

"And what does that tell you?" Kakashi asked, thinking along the same lines as Shikamaru.

"That either they're cocky, it's a trap, or they know there's no way anyone can pass."

"Or all three."

Shikamaru nodded. "Allowing them to call for aid could go either way. The test could be rigged, so they know it won't matter. They could also have something up their sleeve to take out the person they appoint as test-taker."

"Faced with a situation like this, I would assume it's a trap. Which is why you won't be going alone. However…" Kakashi leaned forward in his chair. "I'm thinking you should elect who joins you for the mission."

"You want me to decide who goes?"

Kakashi shrugged his shoulders. "I think it's only fair. It's not like you haven't picked your own team before. And for a mission like this, I think it's imperative. You know what you need for this mission."

Kakashi was right. If someone else chose the members of his team, it might not work, depending on what the town's leader had in store. Shikamaru was already coming up with ideas for how this mission could go.

Shikamaru stood where he was and thought.

Assuming this was a trap, he had to be prepared for the possibility of the town having gathered their own group of people to make sure this deal went off without a hitch. This meant they could have hired highly trained individuals or shinobi from another village. Facing people with a high level of skill meant he had to stack the odds in his favor by putting versatile people on his team. He had to maintain balance, though. If one piece on the board had too much power, he couldn't risk losing it to an enemy.

A three-man squad would be perfect for this. He didn't want to crowd the board, or make things obvious to the enemy. Too big of a group would be easily spotted. More people meant more of a threat. If the enemy felt intimidated, they would either run or get reinforcements.

Dressing as a traveler wouldn't help maintain their cover. Whether or not the enemy knew he was a shinobi didn't matter. The town's leader probably had spies in the village to keep an eye out for any newcomers. They would target the ones they didn't recognize, whether they wore a headband or not. Allowing the village to appoint someone from outside the village indicated that they had a pretty good idea of who was in the village and expected them to look beyond their boarders. Shikamaru couldn't transform into someone he hadn't seen before, so it was impossible to pretend to be a regular villager. Same thing went for his teammates.

They would not know what the test was until the town leader administered it. This was a problem for a number of reasons. The most obvious was that the town leader could change it at any time. This meant that he probably did have spies in the village to evaluate the most promising for the test and change the test accordingly. Not knowing what would be asked meant they couldn't prepare. Not that it mattered if the test was rigged.

Only one could take the test. That was important.

If Shikamaru showed up with a team, they would automatically be targeted. They would assume any stranger would be there for the solitary purpose of taking the test. It wouldn't matter how many people he brought with him if they would all be targeted. Switching places with a villager would make things trickier but without knowing who in the village was a spy, it was a risk. Besides, a villager wouldn't be able to transform themselves to look like the shinobi who took their place.

If they would all be targeted, it wouldn't make sense to have other highly intelligent shinobi in the group as back-ups.

Attacking the shinobi would be risky, even for other shinobi. Their enemy probably knew this and would try to be sneaky about it.

Would they attack all three of them just to cover their bases or would they hone in on one individual? If the latter, how would they know which was which? Their mannerisms might give them away. If they acted or spoke differently, it might camouflage them. Their position would help give them away. If Shikamaru stood flanked by the others, the enemy would presume him to be their target.

The other question was how would the enemy dispose of them? Killing them over something like this would be a little much. Most likely they would find a way to incapacitate them. Depending on when the test was held, it seemed risky for the enemy to simply kidnap the one they believed would take the test. All that time ran the risk of their hostage getting away or their teammates fighting back. Keeping them busy with a fight was too direct and flawed. Knocking them out would be the easiest and best way to do it. If asleep, they would not be harmed but unable to take the test. They would wake up after the test was already over.

"Have you decided?" Kakashi asked, seeing how long Shikamaru was taking to form a team.

Shino's insects could break down different poisons and certain drugs, but that would only spare him. Shino could take the test but, as intelligent as Shino was, Shikamaru wasn't confident he could solve riddles as well as he could. The test might be time-sensitive, too, and Shino might not be able to answer them quickly enough, even if he could solve it.

Sakura was smart and skilled, but she was book-smart. He had no idea if she was good at riddles. She would be able to neutralize whatever drug was given to one of them, in theory.

Actually, it might be best to neutralize the threat instead of treating themselves after they struck in this case. Which meant…

"Still thinking?" Kakashi prompted him.

Shikamaru looked up and gave an affirmative nod of his head. "Ok, I think I know who I want to accompany me."

He had already come up with numerous possibilities of attack from the enemy, but to best succeed, he needed to eliminate as many variables as possible.

"I want Ino to join me on this mission."

Kakashi nodded. "I see. Her skills would be useful on this mission, plus you work well together."

"Her medical ninjutsu would certainly come in handy for this mission as well as her jutsu skills. If we were to use tech to communicate, we risk the enemy hearing us or seeing us speak to someone with an ear piece. Using her jutsu, we can relay information to each other without the need of verbal communication. It's more efficient and safer."

"I suppose you'll want Choji to come along as well?"

"This isn't a social thing," Shikamaru said, half annoyed. "As well as we work together as a team, I'm afraid I can't utilize Choji's skills on this one. He understands that it isn't personal, picking Ino and not him. For the sake of the mission, we have to use the best tools for the job. Besides, he's probably happier staying here eating. They just opened up a new place down the road and he's been dying to check it out."

Kakashi chuckled. "I figured as much. So, who's your third teammate?"

Shikamaru was half-reluctant to say, knowing how both parties would react. "Naruto."

Kakashi's brows disappeared under his unkempt bangs. "Really?"

"Don't give me that sound," Shikamaru complained. He knew Kakashi would react this way. "He's got the skills I need for this mission. He can use his clones to help us stay ahead of the danger and they'll last longer than any we can make. And having him being him might actually offer us some cover."

"Meaning it'll be obvious to the enemy that he isn't the one they're after?"

"Don't tell him that part," said Shikamaru. "Then he'll try to sound smart on the mission."

"It's not like it won't still work in your favor. Him trying to sound smart will only make it more obvious that he isn't their target."

"He is smart, just not this kind of smart."

"Well, fine. Fine. Bring him. I'm sure he's itching for something to do."

Shikamaru was lost in thought again, dwelling on something he said just a moment ago.

"I'll round them up, I said," Kakashi said a little louder to get Shikamaru's attention.

"Huh? Oh, sorry. I was just thinking about something."

Kakashi smirked. "I'm sure you were. Shame Temari had to go back to the Sand. I'm sure she would have loved to accompany you."

Shikamaru's face turned bright red and he looked at the wall. "I wasn't thinking about her. And it's not like she would come along anyway. She's under no obligation. This is a mission."

"Yeah, but having a pretty girl around makes it hard for a man to think straight. It'll be easier for you to maintain your cover."

"Just call Ino and Naruto and tell them to meet me at the gate. I gotta go pack." Shikamaru hastily opened the door and left the office, wanting to escape Kakashi's teasing as soon as possible.

"You just want to get away from me," Kakashi called through the closing door.

"You're a genius," Shikamaru called from the hall.