The Assassin in the Smoky Shadow

A/N: A third Naruto idea. No idea how it will turn out. Writers should feel free to borrow any of my Naruto ideas if they'd like to use them in their stories.

Setup: Naruto holds the Kyuubi, but no one knows Naruto is still alive. Sandaime believes the boy died in the hectic aftermath of Kyuubi's destruction. Instead, Naruto has grown up in a for-profit orphanage run by a rather despicable man.


A chuunin patrolling the walls of Konoha saw something weird on the ground. He leapt off the wall and walked through a dingy alley. This was a rather poor part of the village, unclean and smelly. But it didn't phase the chuunin.

He walked forward slowly wishing he had more light. Alas, the moon was only at a quarter and the sky was filled with clouds. But he had seen something from the wall, something shimmering.

The seconds ticked away as the chuunin, Chunky to his friends, crept up on…a scene of horror.

A man was dead…and the blood was everywhere. Some moonlight must have struck the blood to attract his attention. Now it all just looked like inky tar. Chunky felt sick, terribly sick, but managed to witness the scene well enough to describe it before departing for a police team. The dead man's clothes suggested he was a civilian, after all.

In his haste to get away, Chunky didn't notice the oddly deformed kanji that coursed on the forehead of the dead man. It pulsed like it was made of smoke…or shadows. And, if one squinted a bit in the darkness, it looks like the kanji said smoke…or perhaps, from a different angle, it said shadow.

It was a puzzle.


The Sandaime Hokage didn't usually visit the murder scenes of civilians within Konoha. After all, that was what the council was for: to deal with trade and civilian safety and other such mundane matters.

Yet, here he was. The symbol discovered at the scene had pried him away from his morning paperwork and brought him running to the scene.

He had only ever heard of the symbol…but he knew what to look for.

The elderly man bent down near the dead man's decapitated head. Sandaime paled as he recognized it…it was exactly as the Nidaime Hokage had described it, exactly as the First Tsuchikage had described it in a letter in the Archive, exactly as the lurid stories from 'true crime' books described it from murder scenes all over the Elemental Countries.

It was the mark of a Legendary Assassin. The oldest assassin…or perhaps one of his disciples…had used this mark, the Smoky Shadow, to denote his kills for a very long time. Indeed, the mark was first used one hundred twelve years ago. The Professor's mind let very little slip by him.

"Who was this man?" the Sandaime asked.

"Hokage-sama, he was a humanitarian. He ran most of the orphanages around Fire Country."

Sandaime frowned and shook his head. "Dig deeper. Someone paid a lot of money to have this man killed. This mark proves that. He did something to anger someone very powerful or very wealthy. We must discover who this man really was."

The police investigator nodded, but he was obviously confused. Why did the military ruler care about this case?

"I will look into it, Hokage-sama…"

"I want a copy of the report when you're finished."


Sarutobi walked slowly back to the tower. There was so much he didn't understand. A humanitarian killed this way…orphans…what could be important enough about orphans to get him killed?

It made no sense. The Smoky Shadow's mark hadn't been seen in Fire Country since before he was Hokage. Why now? Why this target?

Why couldn't the Legendary Assassins have faded into legend?

It was hard enough fighting against conventionally trained shinobi, many of whom possessed unique bloodline talents, but to face enemies who never announced their presence and who never seemed to fail. Sarutobi was too old to be Hokage.

One day very soon he'd have to name a successor. Perhaps Jiraiya would stop writing his smutty books and return to Konoha. Then again…prostitution was illegal here, so Jiraiya would rather be elsewhere.

Sandaime returned to the tower and sought comfort in his private library. He pulled down the scrolls that dealt with the Legendary Assassins.

"Eight of them," he mumbled.

"Six are presumed dead as their marks haven't been seen in a generation. But the Smoky Shadow is still around after a hundred years. Must be teacher and apprentice time after time. Dead Daimyo's; dead samurai and shinobi; they can kill anything…so it says.

"Ah ha. I remember this quotation. 'Ninja attempt to fight to their strengths; the legendary assassins fight to their opponents' weaknesses…' It is a very different school of thought."

Sarutobi took a moment and he could imagine a dozen different ways he might fall to a true assassin. Sandaime Hokage had no shame in admitting to himself what sort of weaknesses he possessed. But he couldn't see many opponents fighting him directly and winning…it would be the indirect attack only that might win. Something like what Orochimaru would do, the bastard.

Could he somehow put out a contract that would interest this Smoky Shadow? Bring him or her out into the open? Sandaime had to protect his people, after all, and an assassin operating right under the noses of a thousand ninja inside Konoha made him nervous.

The Hokage continued to fret until an out-of-breath (and rather portly) policeman was ushered into his office.


"Report on the murder last night. Preliminary conclusions, Hokage-sama."

"Your man discovered something?"

"Missing children from the orphanages and a larger than expected bank balance."

Sandaime took the report and quickly skimmed it. Then he closed his eyes and sighed. Evil could operate even inside Fire Country…even at the cost of enslaved orphans.

"Thank you. I will request a commendation for your whole team for discovering this so quickly."

The policeman left…and Sandaime changed his thinking. This assassin killed an evil man…but why? Apparently no one in Fire Country even thought about the welfare of orphans if this 'humanitarian' had been able to make so many children disappear.

But someone noticed…and someone put out a contract…over orphans. Who? And why would the Smoky Shadow accept it?

There was a mystery here and Sandaime Hokage didn't like it at all.


A small blonde-haired child moved quickly through Kenshi, a village twenty-eight kilometers outside Konoha. He knew how to move without being noticed…and no one did.

How to hide in the shadows; how to hide in plain sight; how to hide when posted on guard duty.

Naruto had been training for two years, since he was four. A man, now his sensei, had come across the hyperactive little boy in dirty, dingy clothing…and seen something of value.

Since that fateful afternoon, Naruto had learned ancient methods and a code of ethics passed from master to apprentice for more than a hundred years.

Everywhere he went, Naruto carried two small blades he could easily hide on his body. He was small…tiny, really…and no one would ever suspect him of holding the power he did. His sensei knew little of chakra, so Naruto wasn't picked because of the seal on his belly that granted him exceptional power. No, he was picked because of the power of Naruto's will.

His will to be powerful.

His will to be great.

The boy made his way through a maze of side streets and alleys before he arrived at the designated spot. His sensei stepped out of the shadows and smiled at his young apprentice.

"He will not be able to send my friends away. Not ever again," Naruto said.

"It was an…appropriate…selection, my new apprentice. Scum such as that man should not be allowed to live. As for you, Naruto, you have passed your trial. You will begin taking contracts I select for you. But, your next bit of training will be difficult."

"Hai, sensei."

"You were just another thrown-away child. But you have become powerful because it is your nature…and I have helped here and there. Now, you know the foundations of all that I know, all that I was taught. To master all of it will take twenty years, many successful contract completions and many near failures. You must learn those lessons on your own. But, you can be greater than even my sensei was as I believe you can learn more than the blade and the way of stealth. You can learn the way of the ninja, too. Never forget what you know now, never stop practicing it. But integrate my way into the ninja way…you will make it your way, my apprentice."

"Hai, sensei."


"Your next challenge, then. In three weeks, you will travel to Konoha and enter the Ninja Academy. For six boring years, you will endure. You will learn all that the school has available, even the things it doesn't teach students, mining the library, pestering your teachers day and night, that will be your public face. The goof, the hard-working prankster. In private, you will steal one scroll per week every week and remain undetected. Begin by stealing from low risk targets; by the time you are ten, you should be stealing from people at your teacher's rank and higher. You have that week to learn the technique on the scroll. Be sure to copy the scroll somehow to form a permanent library for when you train your apprentice."

Naruto nodded but seemed troubled. "Will you remain my sensei?"

The cloaked man smiled. "For the rest of my life, I will be your teacher. You just became my true apprentice since you passed your test. I will be in touch often, but I have my own duties to attend to, of course.

"I am not throwing you into this training as busy work, Naruto, remember that. Ninja techniques are things I was never able to learn, so I followed the path of the samurai. You, my apprentice, will have every sharpened tool available in your belt. Understand?"



After six fruitful years of skullduggery, Uzumaki Naruto, the dead last of the Konoha Ninja Academy, was finally graduating, after failing his final examination twice.

He delighted in pranking the villagers, mocking the ANBU, and generally acting as a lovable menace everywhere he wandered.

Of course, he had also rifled through every scroll in the academy, stolen dozens from the mostly abandoned Uchiha compound, discovered the secrets of the Hyuuga, Inuzuka, Aburame, and many other clans, and had even learned how to break into the Hokage's private library.

Instead of completing his sensei's requirement that he acquire more than three hundred jutsus during his time in Konoha, Naruto had documented and archived more than fifteen hundred and had learned more than five hundred. He had only a handful at the B- or A-rank, but one could kill with a D-rank jutsu if it was used just right.

The S-, A-, and B-rank jutsus were mostly too flashy, too destructive, and too loud for an assassin to use them with any level of stealth. Still, he would eventually learn them so as to seem a decent, if not feared ninja.

Naruto kept up his true profession – with the sharpest of skills – by executing a contract or two every month. On the weekends, Naruto was famous for leaving the village to go fishing. Every weekend, no matter the weather. It just so happened that among all the fish he caught were a number of syndicate members or corrupt politicians or lower-level samurai who had gone rogue.

He did not sign any of those killings, per the advice of his sensei. Indeed, per the tradition, Naruto's sensei signed only one killing a year with the distinctive Smoky Shadow mark. It was just enough to remind people that the Legendary Assassin was still around, but not enough to tell people where he had been or where he might be going.

Naruto walked quickly from the academy building with his new hita-ite on his forehead and a big dopey smile on his face.

He ran down the street yelling random slogans and then stopped when he noticed a distinctive chalk mark on a particular building. To the world, it said, 'grafitti.' To Naruto, it said, 'meet with your sensei.'


The hyperactive blonde turned and began to run to a particular ramen stand in Konoha. Meets were pre-determined, usually at ramen stands or other purveyors of street food.

"Ramen," he shouted again. It wasn't an uncommon thing to see on the streets of Konoha. The young man could be peacefully minding his own business when all of a sudden he began shouting about junk food.

Unpredictability of this sort was a powerful disguise.

Naruto arrived at the designated ramen stand, which changed every meeting, and began ordering bowl after bowl. Eventually, the satiated Naruto smiled, burped, and seemed to slump over on his table taking a little nap.

Instead, he was waiting for his sensei.

A few minutes later a stumble-down drunk shambled into the stand, bumped into the sleeping Naruto, and then managed to stumble over and order some ramen. He ate it standing up and then promptly left.

Twenty minute later, the stall owner prodded Naruto awake and demanded that the new genin leave so that other customers could sit down.

"Alright, alright. I'm going. But I'm not coming back for a long time. Rude!"

Naruto quickly made his way home and set up a privacy jutsu. Then he took off his cloak and dug into the special concealed pocket where his disguised sensei had put the message.

"New contract: Mizuki, instructor at Konoha Ninja Academy. Suspected spy implanted in Konoha. Received orders to leave Hidden Leaf within three days. Neutralize target outside the confines of Konoha. Client requests the death to appear an animal attack. Highest stealth required.

Next meeting: Badi Udon."

Naruto allowed a fire in his hand to consume the note. Mizuki. Naruto had never cared for the man…but he hadn't suspected him of being a possible spy.

Interesting. People could be endlessly surprising.

Naruto wondered about how to deal with the man. It was rather a long window of time….

That was when Naruto saw many people running around outside. "The Scroll has been stolen," some idiot of a shinobi shouted.

It was enough for Naruto. A spy might very well drop all his masks as he prepared to depart. This 'scroll' people were screaming about could very well be a sign of Mizuki's departure.

With a brief smile, Naruto evaporated into wind and was gone. He had killed many skilled people before, but never someone trained in the ninja arts. With any luck it would be fun.


Naruto was a superb estimator. He could look at five likely outcomes and estimate which one would come true. Already, Naruto was more skilled in this assassin discipline than his sensei was.

In this case, Naruto was sure that Mizuki would be fleeing north through the deepest part of the forest surrounding Konoha.

Such a path would make it hard for people following Mizuki to track him…but it was an obvious choice to anyone who studied the way spies and traitors thought.

Ninja were so predictable.

Mizuki crashed through the forest sounding like a dozen rampaging pigs. Naruto stepped from the shadows perhaps twenty steps from Mizuki and got within a foot before the man looked up from his attempt at catching his breath.

"Who are –," was all he got out before Naruto used the device he'd cobbled together. It was designed to match precisely the marks made by the massive bears that roamed the woods.

Mizuki lost his right hand.

"What… Naruto, is that you? What are you doing?" The whining and screeching was beyond bearable right now.

Naruto didn't have time for talking. The ANBU chasing Mizuki would be here within moments.

The second slash with the massive, five-bladed weapon ripped through Mizuki's chest.

A third attack, from the left this time, tore out Mizuki's throat.

A few more swipes shredded the man's clothing. Naruto made sure to spread out whatever the man had on him…as if a bear had rooted through looking for anything interesting.

In that vein, Naruto did find one thing of interest, a massive scroll in the dead man's bag. Naruto pulled it out, slashed it a few times and let some of the paper remain on the ground. He took the massive scroll and tucked it away with his five knived weapon.

Naruto walked carefully away. He surveyed the scene and had only one thing out of place: footprints. A gust of wind, an E-class jutsu, cascaded through the area, erasing the footprints Naruto had made.

The whole attack had taken forty seconds.

Naruto sunk back into the shadows barely thirty seconds before the ANBU stumbled onto the grisly scene.

He had a massive scroll to study, didn't he? If it was worth a spy stealing it then it was probably pretty damned interesting.


Naruto looked over at Tazuna the Bridge Builder and wondered how such a slight man could drink so much sake. He looked like a hobo, how could he even afford a single bottle?

Naruto tamped down a strangled sigh. Life as a shinobi was dead boring.

This was the first time he'd even left Konoha as a shinobi and it was all to protect the lush…protect from what? The man wouldn't say. It set off all Naruto's warning bells, but apparently not the Hokage's or his jounin-sensei's.

This was the reason a non-chakra-using assassin could kill ninjas. They were smart, most of them, but they had under-developed common sense facilities.

Item, if a story sounds suspicious, it is. Investigate.

Item, if a lush drinks a lot, seems nervous on the road, and refuses to talk about what sort of idiot 'bandits' would try to attack someone who looks broke, probe at his story and break it apart.

Item, if you have a three-person team to lead, teach them something. People don't always learn best on their own. Jeez, the man supposedly knew a thousand techniques. Teach!

Naruto sighed again. Maybe it would have been better to do like his sensei had and join up with the samurai. Naruto's mind wandered for a while until they passed through a small village…and Naruto saw some familiar graffiti.

"Hey, Kakashi, can we stop for ramen?"

"They won't have a ramen stand."

"Okay, some udon then. Something. I'm hungry."

"Fine," the older ninja said, just to get his charge to shut up.

Five minutes later, Naruto proved that the town had a small ramen stand. And before the team left, Naruto had the details of his next contract.

Unfortunately he wouldn't be able to read the details until much later, after pretending to be a drooling idiot in the face of the Demon Brothers and doing a bit of damage to the self proclaimed expert of silent killing. Bah.

Zabuza was too flashy and showy to kill anyone silently. If the man had really wanted to kill the Mizukage all those years ago, then he could have. Typical ninja: idiotic.

It was later that night that Naruto had time to himself and dug out the small scroll.

"New contract: Gato of Gato Corporation. Billionaire; smuggling; shipping monopoly; extortion of most of Wave Country. Water Daimyo put out the contract to ensure Gato doesn't try these same moves back in Water Country. Mark this one with the Smoky Shadow; it's a worthy contract. Present location unknown. Contract payment is quite generous."

Naruto shrugged, a bit surprised by how his shinobi task and his other work so neatly coincided. His sensei had probably discovered the assignment and thought it perfect as Naruto was already on his way, legitimately, to Wave

Naruto wondered about dealing with the man's subordinates, like Zabuza.

In the back of his mind, as he turned to sleep for a few hours, Naruto guessed at his sensei's response.

"Only kill them if it amuses you. We're paid for Gato. Don't put yourself at risk to kill someone unimportant."


Naruto waited until the next evening before using a strong sleeping genjutsu on everyone in Tazuna's home. Even the annoying grandson Inari went right to sleep.

As he left the home, Naruto thanked Kami once again that Shino wasn't on his team. Indeed, as useless as Uchiha and Haruno were, they had no special talents for seeing what Naruto really was or what he really did with his spare time. A Hyuuga or an Aburame would be difficult teammates to have; even an Inuzuka.

But Shino would be the worst. Naruto could make a genjutsu work on a dog, but he had no idea if it would work on a hive of insects.

He didn't particularly wish to find out.

Naruto stuck to the shadows as he made his way to the nearest Gato Corporation building, three villages over. From there it took a few minutes of listening to discern that Gato was nearby visiting some 'minions.'

He snuck into the building and eventually found a map on the main thug's desk. It was a wonder such a stupid man had made himself a billionaire. Did the competition just flop over and surrender?

It took Naruto forty minutes to make it to a run-down cabin. There were two samurai outside, two inside plus Gato, in addition to Zabuza and that fake hunter nin.

Naruto spied for a few minutes. Gato threatened, Zabuza and the hunter nin threatened back. No one had noticed Naruto…not that anyone ever did.

Gato stormed out of the building a few minutes later. Naruto was down on the field of battle seconds later. One slice: Gato down, contract fulfilled. Second and third slices: two more permanently unemployed samurai. Fourth and fifth slices: all his bodyguards were dead.

Naruto bent down and began the process of affixing the smoky shadow symbol. It required a brush and a bottle of special chemicals. Naruto could probably reproduce the effect with a chakra-based jutsu, but this was the way his sensei had taught him.

Unfortunately signing his work took longer than performing the task. The fake hunter nin came out to investigate.

"You," the voice shouted.

Naruto turned and frowned. He hadn't planned to tangle with these two tonight. Too bad his plans for a peaceful contract were now blown.

A flurry of senbon erupted from the hunter nin. Naruto brought up an earth wall. Moments later, the hunter nin trapped Naruto in a kind of icy prison. It took Naruto a few tries before he cracked it: fire didn't work, direct force seemed to do nothing, lightening-style attacks did nothing…so Naruto tried a sound-based attack, a D-rank.

Seconds after launching it, the ice cracked everywhich way. The hunter nin seemed stunned that Naruto had been able to deal with this ultimate weapon so quickly.

Naruto took advantage of the hunter nin's disorientation and went on the offense. He pulled out his twin short blades and used the back of the blades to knock out the major nerve clusters that allowed the hunter nin to have conscious control over his body.

Three hits and the hunter nin stopped moving, but continued to breathe. The effect should last a goodly while. Naruto went inside the cabin to deal with Zabuza.

"You weren't part of the contract. I'd have probably left you alone, but your partner interrupted me. Goodbye, Demon of the Bloody Mist."

Zabuza had tried to shield his face, but the blades went through flesh and bone as easily as they went through a ripe pumpkin.

Naruto took a few minutes to root through the cabin. He found a few scrolls and a massive sword. He took everything. Then he returned to interrogate the hunter nin. The mask came off first. The boy had a very pretty face, but it still looked boyish. A search of the hunter nin's clothing revealed a senbon pouch and three more scrolls.

Then Naruto finished the task of marking Gato's face. He returned to the hunter nin and fashioned up some chakra threads strong enough to keep even a Kage tied up.

Naruto then tapped on the nerve clusters again and the hunter nin awoke once more.

"What's your name?"

"What have you done?" the boy asked with a hoarse catch in his voice. He knew, or guessed, that Zabuza was dead.

"I had a contract for Gato…but you involved yourself and your former partner. Now…your name?"

"I will kill you."

"I will call you Snotty then."

"Haku. My name is Haku."

"Why were you able to even get a spell to affect me? I'm faster than stupid ninjas."

"Maybe I am, too."

Naruto paused in his questioning to process that statement. "You were trained by an assassin then?"

Haku went pale at that comment.

Naruto took this as confirmation. "You can't mean to tell me that Zabuza was one of the Legendary Assassins? He's famous for his failed attempt at killing the Mizukage."

"I have nothing to say."

Naruto noticed a necklace on the other boy's throat. He pulled it out and saw a symbol.

"My sensei trained me in recognizing the symbols of the other Legendary Assassins. You were trained by the one who used the Swirling Water kanji to mark his work. He wasn't that tough to kill."

"Not when he was recovering," Haku shouted.

Naruto just nodded, glad for the confirmation.

"You should have minded your own business, Haku. I am sorry for this." Naruto then removed the boy's head.

It took a few more minutes to remove any trace that he'd ever been there. Another seventy minutes later and Naruto was back in Tazuna's house. The sleeping genjutsu would fail at sun up.

Naruto was untroubled by dreams as he slept. Digging through Haku's scrolls a day later was another story: how to perform one handed seals, how to learn to manipulate ice, like that weird mirror prison, and many other useful skills.

A treasure trove from a somewhat worthwhile opponent.

He'd remember the name Haku.


After the rest of a pointless mission to guard Tazuna (as his opposition was already dead), Naruto and company returned to Konoha and began to prepare for the Chuunin Selection Examination.

Naruto was instructed to get into the finals of the chuunin exam, but to behave in such a way he wouldn't be promoted. Specifically he was given a contract…to kill, publicly, the Kazekage's son, Gaara. It should be done in a way that would cause diplomatic difficulties for Hidden Leaf but leave Naruto mostly blameless. It was the trickiest assignment he'd ever received.

Of course, Naruto hadn't counted on running into the S-ranked Orochimaru inside the Forest of Death. Naruto had almost had to reveal some of his true skills but he was able to cut the Sannin's Achilles' Heel in a seeming accident when the long-necked freak was attacking (or kissing) Sasuke's shoulder.

Nothing is more devastating to a warrior than a destroyed Achilles' Heel, save for the loss of a whole leg or arm.

The Sannin escaped…and Naruto began plotting to do a free contract in the near future. He hadn't liked being swallowed whole by a giant snake summons.

Now he was in the finals, as required by a contract. He'd disabled the whirling dervish of a Hyuuga by using an earth jutsu to dump sand and rocks on top of him when he was spinning. Instead of being a deadly combatant, he acted more like a stone tumbler, with rocks and dirt getting trapped inside with him, the stones pummeling his body while Naruto did nothing but hide from Neji's attack. When the pain became too great, Neji crumpled to the ground looking like a pile of hamburger, broken bones and all.

The audience was shocked. No one had ever thought this Hyuuga finishing move could be countered so easily…but no one had had a month to dissect the technique and create a simple counter for it, either. Instead, ninjas just fell to it time after time. After this public demonstration, that technique would be useless. An A-rank technique foiled by a D-rank Earth jutsu. Ha!

The second round, Naruto versus Gaara, was more interesting. Naruto had seen Gaara fight three times now: once in the forest, once in the preliminaries, and once with his first round opponent.

Dealing with Gaara was, fortunately, easier than dealing with Hyuuga Neji. The Hyuuga prodigy was actually skilled as a ninja, limited in scope, of course, but skilled.

The Skukaku container, Gaara, had no skill. His demon gave him all of his power. Naruto had known for some time about the Kyuubi sealed into him, but he'd never been tempted by its demands or offers.

All of Gaara's skills as a ninja came from what the sand could do. Disable the sand…and you've disabled Gaara.

Naruto began his attack as he listened to what Gaara said, his crazed mumblings. Step one, a D-ranked water jutsu to wet the sand. Step two, a C-ranked genjutsu to reverse the directions Gaara saw in his mind. Left became right and such. Step three, a mere kunai thrown at Gaara, and designed to miss, obvious to everyone in the stands. That is, until a few inches of still-dry sand rose up to protect Gaara by diverting the kunai…right into Gaara's neck.

The demon container's head was nearly cut off his body.

Naruto looked properly shocked, of course, but he was glad that his contract had been fulfilled so easily.

It would have been hard, if not impossible, to engage Gaara directly. Weapons against sand; fire or lightening against sand; not much would have worked. But water weighed the sand down…and Gaara was such a weak shinobi he couldn't even detect a minor genjutsu. In effect, Gaara's sand had killed him.

Perfectly lovely.

Naruto felt relieved…until he saw the impossible. Orochimaru in the top stand attacking Sandaime. Most everyone in the stands asleep…as the result of another genjutsu.

And a massive invasion underway.



The invasion had gone badly for Konoha. Thankfully, the Suna portion of the attackers had fled after Gaara's death. Unfortunately, the devastation caused by Sound was more than sufficient. The Third Hokage was dead. The walls were destroyed in major sections. Ten percent of the Hidden Leaf shinobi were dead; another third were injured to some extent.

Now this creepy man with extremely long hair was insisting that Naruto accompany him on a mission. Kakashi didn't have anything to say against it, so Naruto left.

Also, in another oddity, Naruto had received his first two "complete-when-possible" contracts. Massive money had been placed on the life of Orochimaru and a substantial amount had been placed on Kabuto by the family he betrayed back in Hidden Leaf.

Anything that got him out of the village and closer to these two targets was worth the aggravation of a self-absorbed pervert like Jiraiya.

Apparently, he and the old geezer needed to find another geezer, a lady who was bad with the cards.

Naruto could put two-and-two together. One of these two geezers was to be the new Hokage…and these were the people who knew Orochimaru best. A good place to be to execute on his contract.

It was a few days later when Naruto and his pervy 'friend' finally arrived at the village where Tsunade was digging herself deeper into debt.

After much huffing and puffing, Jiraiya and Naruto more or less convinced Tsunade to think about returning to Konoha, if for nothing more than to help heal survivors of the attempted invasion.

In the time before Tsunade had set to make up her mind, Naruto managed to worm his way into Tsunade's apprentice's good graces. Shizune had told Naruto much about the medic ninja life…and much that could help Naruto against someone like Kabuto.

Naruto learned a good deal about chakra scalpels and how useful and nasty they were, particularly in a combat situation.

He had time, a day or a week or a month, to figure out how to beat Kabuto and then Orochimaru.

Naruto continued chatting with Shizune…and continued plotting.


Kabuto's death had been anti-climactic. When he and Orochimaru had come to force Tsunade to heal the Snake Sannin's severed arms, Naruto had lured Kabuto into the forest away from the main battle.

When Kabuto opened up with his chakra scalpel attacks, Naruto had only smiled. He figured Kabuto wouldn't succumb to a simple genjutsu like he's used on Gaara, but his ability to self-heal was his strength and his vulnerability. How to trap him as Gaara had been?

The answer was simple. Naruto and a dozen clones had formed up a rough circle a good distance from Kabuto and begun using Air Whips to attack him. The nearly worthless D-ranked air technique was used nowadays only to help those with an air affinity gain better control over their element. It was considered too weak for ninja combat…but not to Naruto.

Two of the clones had kept their whips on Kabuto's arms to keep him from using seals while everyone else forced minor cuts all over Kabuto's body.

As expected, Kabuto's ultimate defense kicked in: he stitched himself up right before Naruto's very eyes.

"You can't harm me…."

Naruto just smiled and the air whip strikes intensified. More Naruto shadow clones appeared; more whips.

Even Kabuto figured out what was happening. Kabuto couldn't be easily killed by a blow, even one that would be fatal to another person. But, he could kill himself trying to heal up all these cuts. Death by a thousand cuts…turned into death by healing a thousand cuts.

Kabuto seemed not to be able to turn off his seal-healing ability. It seemed he'd trained it too well, it was on automatic now, no matter how much he struggled.

He had his chakra scalpels out and was trying to sever the air whips holding onto him…save for the fact that chakra had only been used to form up the whip, not to keep it going. (It was an exercise in molding the elements after all.)

Kabuto could cut the air whip as many times as he wanted. The air sealed up behind the chakra scalpel, like water filling behind the wake of a boat.

It took only five minutes. There was easily a liter of blood on the ground and forty Naruto's whipping away, long, great gashes over Kabuto's torso, legs, and arms. He was screaming in pain, screaming with each new lash as more and more of his waning chakra went to heal non-lethal wounds.

That was when Naruto, the real one, dispelled his air whip and began to use the Sword of Swirling Air (one of the most useful B-rank techniques he knew). Naruto began aiming deeper and deeper wounds at Kabuto's neck. He was so weakened he was barely able to stand any longer.

These wounds didn't heal as fast. Soon, Naruto was hacking through the esophagus, through veins and arteries, and then into the spinal column itself. Ten minutes after the battle started, Kabuto's head lay next to his body. There would be no healing that, would there?

He took a minute to hack the rest of the body to pieces, making it look something like the victim of a partially formed Rasengan, the flashy technique Jiraiya was attempted to teach him.

Why use something flashy when something simple is guaranteed to work? Drain someone's chakra so they get sluggish and then kill them. Duh. Assassins played to their victims' weaknesses, after all.

It was the only way that always worked.


After returning with the Godaime Hokage – who was still upset she hadn't managed to kill Orochimaru – Naruto got a chalk message that he hadn't seen often before.

His sensei wanted to meet…and talk.

It had been years since he'd received anything other than a simple scroll from his sensei. Naruto wondered what this conversation would be about.

A few days later, on a Sunday, Naruto went to Kenshi, the place he'd lived when he'd met his sensei. It had been a few years, but the village looked much the same. Too bad his friends from the orphanage had all scattered to the winds.

It wasn't easy to keep friends as a shinobi and assassin.

Naruto went to the main park and sat on the bank of the stream that passed through town. It was a beautiful spot. Naruto took out a bento he'd packed before he left Konoha and began to eat.

A few minutes later, someone dressed as an old woman sat down close to him. 'She' began to eat as well.

"It's a wonderful springtime," Naruto said.

"I fear for the flood once it begins to rain."

"Even the dryness of Fire can be overcome by the tenacity of the Leaf, right?"

"Indeed, Naruto. How have you been?" In a world where henge was taught to every shinobi ten and older, it was a good idea to have a few codes set up.

"I am well. It is good to see…well, speak to you."

"I apologize for the disguise. It is easier for a man to completely change his appearance by adopting the guise of a woman than of another man…."

"Kabuto is dead."

"Excellent. Was it a challenge?"

"Only in that he picked the time to attack. You and I both prefer to set the timetable. Surprise is a most potent advantage after all."

Naruto's sensei nodded as 'she' began to eat pickled daikon.

"I think you have exceeded my every expectation, Naruto. You have heard the expression, one can't turn a sow's ear into a silk purse? That's what you've done with your particular form of ninja training. Learned every sort of simple technique, armed yourself with the smallest sort of weapons, the things most people forget or throw away…and you, with simple techniques, can take down demons, or snakes, or someday Kages.

"Now, it is time. You are a full three years younger than when my sensei had this conversation with me. It is time for your master work."

"Really, sensei? What must I do?"

"You must choose an appropriate target and plan the entire thing yourself. You must also mark your victory with the Smoky Shadow."

Naruto nodded as he continued to eat, dipping his bare feet into the stream from time to time.

"There is one man…appropriate…for such a master work," Naruto said. "Orochimaru, the one who nearly killed me with a snake summons in the Forest of Death."

"That's ambitious. I myself am not ashamed to admit I would fail in an attempt on his life."

"Only because he uses chakra based traps you cannot sense."

"That is likely true. How do you propose to do this?"

"I will attack him in his place of power, where he feels safest. And once he's dead, I will drag his body out and level everything else."

"This is a master work, Naruto, not a treatise to the world about your hatred of the man."

"A master work should speak of its author, sensei. This will be impossible for anyone to deny: that the Smoky Shadow remains the strongest, and perhaps only, assassin left in the world."

"And how will you follow this up in a few years for your legendary work? Mine took me five years of planning before I decided how to do it. Killing a Daimyo in front of all his samurai…it was not a simple thing to do."

"But you did it right. That swordsman, Kisame, is still wanted for killing a Daimyo. Many have killed Kages, such as Orochimaru or that Sasori fellow, but all have been immediately exposed for their crimes. You, master, are the only Daimyo killer to have ever escaped detection…."

"And, when it is time, Naruto, you shall design an even greater Legendary Work. For now, concentrate on your masterwork. I will return to speak with you in three months on your plans for Orochimaru. I want you to convince me it will work…and then tell me the ten ways it could fail. You must think this through and plan. He will be your hardest target yet…by far."

"Hai, sensei."

"This scroll will tell you the details of how to access the various underground contracting groups, the ones that put out the jobs you and I have been working on. Be sure to understand all of it, as you'll be responsible for finding your own contracts once you become a master. Good, see you later, Naruto."

With that, the old 'woman' got up from where 'she' had eaten lunch and left. Naruto stayed for another hour, pondering.


Naruto was still a genin, after all he had killed a Kazekage's child. He had demonstrated the requirements to be a chuunin, but the politics kept him from being promoted. Perfect. Naruto didn't need to advance in rank very quickly. He needed to be as invisible and thought as harmless as possible.

His master work, however, had consumed seven months of his life. Now he was in the final stages. He had purposely allowed himself to be hurt while training with Team 7. Or rather he'd used a genjutsu to suggest he'd been horribly maimed by one of Kakashi's stupid training exercises. Make the stupid, incompetent teacher feel a bit of guilt, if he had a conscience.

After all, his prize students continually moaned about how he needed more power so he could kill his brother. Blah blah blah.

Now, step two, he was on his way outside of town while a shadow clone remained in the hospital.

Step three, which was easier than Naruto had planned, was to use the information he'd purchased from a disaffected person inside the Sound hierarchy (done through a few levels of intermediaries). He had a good idea of where Orochimaru would be and how he would be protected: four bodyguards or perhaps five.

But the reality was much simpler. Orochimaru was mostly alone in a darkened room inside a concrete complex when Naruto arrived. His bodyguards were off elsewhere. Indeed, Naruto had only needed to deal with a handful of medic-nins who seemed to be hovering over Orochimaru's pitiful body.

Naruto knew better than to attempt to directly attack the Snake Sannin. Even in his pitiful state, he could probably still attack and harm Naruto.

However, he henged into the guise of one of the dead medic nins who usually hovered over Orochimaru. Since the man was in an oxygen tent, Naruto didn't have to worry about concealing his smell, either.

Naruto went into the room and poked around for a while before he realized his biggest opportunities lay with that oxygen tent. If Orochimaru's failing body needed that much oxygen in order to survive, then Naruto could either let the body fail…and it would without a new host body to move into…or he could help things along.

As he left the room, Naruto quickly discovered a horrible room, 'Experiment Room 17,' wherein he found a carbon monoxide pump. Kami only knew what sort of experiments Orochimaru performed on living subjects with carbon monoxide…but Naruto had use of the machine.

Five minutes later, his blood thoroughly saturated in carbon monoxide, Orochimaru was dead. Still, Naruto sliced the body into an even dozen pieces just to be sure. Who knew if Orochimaru could do some of that same self-healing that his servant Kabuto had been able to perform?

It took ten minutes to lay Orochimaru remains on the ground outside the concrete bunker, paint them with the Smoky Shadow, and return to the complex and line it with powerful explosive notes, all interlinked.

Naruto sent a burst of chakra through a chakra string and watched as hundreds of small explosions weakened the structure…and then gravity did the work of imploding the structure in upon itself. This base of Orochimaru's was no more. He was no more.

Naruto thought that his masterwork was complete.

However, the trip back provided for quite a bit more excitement.

He had a variety of Orochimaru's bodyguards to kill…along with Uchiha Sasuke who had just surrendered himself over to the Snake Sannin's mercies. Naruto took great pleasure in letting all six of them run through a series of rainy puddles…before he threw down a powerful but almost invisible lightning jutsu. All the strong people collapsed unconscious not even aware they were under attack.

Why couldn't ninja be more subtle…more aware of the traps that nature herself leaves everywhere? Well, it was a good thing, otherwise the world wouldn't need true assassins.

Twenty minutes later and the unconscious all became the dead. Decapitation, Naruto's favored method, works in nearly every case. The bone-like man had been hard to kill, even unconscious, but the rest were no problem.

Naruto took the time to mark every one of the dead with the Smoky Shadow before resuming his rapid pace back toward Konoha.

He'd make a miraculous recovery tomorrow from the hospital and no one would be the wiser. He'd be all better in time for Uchiha Sasuke's funeral.

His master work was a complete success.

He and his sensei would celebrate this triumph privately a few weeks later by enjoying a lunch together near a small village in Wave Country.

No one knew the extent of Naruto's accomplishment, save for his sensei, but that was all that mattered.


Eight years passed. Naruto was, to the shinobi world, a rather mediocre chuunin with a prankster's way about him. Naruto was not expected to ever make jounin. It was a good disguise and Naruto didn't want to ruin it.

To the underworld, he was the man who took a difficult or impossible contract every month.

But his sensei was dying and had been unable to fulfill any contracts for more than a year. Naruto felt more than a bit of surprise when he saw a mark on a wall near to his small home. His sensei wanted to meet.

Eight days later, in a small village just over the Fire-Tea Country border, Naruto sat for a meal in a restaurant with an elderly man. Both Naruto and his sensei were disguised. They spoke in pleasant platitudes, but the code revealed much.

The gist: it was time for Naruto to prepare his Legendary Work, hopefully while his sensei was still alive.

The sensei had a suggestion, an assignment for the ages: the Tea Daimyo offered a princely sum for the Raikage to be killed. No shinobi had ever killed a Kage without their identity being immediately spread through the world. Only his sensei, a trained samurai, had ever killed a Daimyo without being caught. It was a legendary task, plus Naruto harbored no warm feelings for Hidden Cloud or its military leader.

Orochimaru made himself an enemy of even more countries when he killed the Third Hokage. Sasori of the Red Sands was a pariah for his actions. Kisame, that blue skinned freak of a swordsman, would never have the same kind of life again for his treachery.

How to do this, Naruto wondered. It would be suicide to follow any of the models of the past: direct attacks, flashy explosions, public proclamations, blah, blah, blah. How to do this the assassin's way? Naruto's way?

When the lunch was over, Naruto's sensei smiled and returned to his public position as the aging captain of the Fire Daimyo's personal guard. And Naruto went back to his life as a chuunin…but he had the fire implanted in his mind.


Three months later, the Raikage hosted a private dinner for all the Daimyos and Kages who had come to attend the Chuunin Selection Exams held in Hidden Cloud.

There were fifty invited guests in the room…and more than one hundred guards. High security; very tense; precisely the sort of mood that made the Raikage smile. He loved showing off his power.

He made a great show of greeting everyone who had come into his mansion. He mingled for an hour before the twenty-one course meal began featuring delicacies from all over the Elemental Nations.

He drank the finest sake made in Rice Country and ate the finest fish and shrimp caught in Water and Wave.

When the gong finally rang, the Raikage went to the Head Table, stood before the largest, most ostentatious chair (even though his guests would be sitting, traditionally, on the floor), and proposed a toast. He knew he was behaving like a bragging child…but one only did get to host the Chuunin Exams every four or five years.

He babbled on for a good long while before knocking back his sake. Then he smiled and sat in his magnificient throne. A few moments later the smell of burning flesh filled the air and the Raikage slumped forward, dead.

Chaos of every sort broke out then. A Kage had died in a room filled with the strongest shinobi in the world. How? Who? Were more attempts in the offing?

War almost broke out over this. Cloud claimed that one of the other Kages had done this. Hidden Sand and Hidden Grass, in particular, resented the implication and claimed that the Kage had been killed by his own shinobi for the man's gluttonous ways and disastrous leadership…but it had been planned to throw the blame elsewhere.

Eventually, after the rhetoric died down, it seemed that the culprit was the chair, the magnificent throne the Raikage had had built specially for this feast.

There was a seal buried underneath all the fabric and padding. It was simple with only two functions. Anyone who sat in the chair had the alcohol in his blood turned to acid. Likewise, anyone who sat in the chair had an odd kanji burned into his flesh.

The chair, literally, would have killed anyone who sat in it had they possessed even the slightest touch of alcohol. But it took someone who knew the Raikage's habits to realize he would have killed anyone else who sat in it (the movers, his wife, his top shinobi, it didn't matter)…and that he would be fairly drunk when he first used it in front of all the other Kages.

Someone had turned the Raikage's less than stellar personality against himself. If it hadn't been so dire it might have been funny.

With that, the Legend of the Smoky Shadow grew. This mythical assassin could even reach out and kill a Kage in a totally secure compound. No one felt safe for a long time after that.


Naruto was now thirty years old, a confirmed lifelong chuunin. He was happy with his lot in life, although his current assassin's task left him stumped.

He had been working on this, err, project for nearly five years now, since just before his sensei had finally passed on. "It will be the hardest thing you've ever done. Done right, it will be greatest, too."

"What must I do, sensei?"

"Enough with the honorifics, Naruto, you passed my standard long ago. Your final and enduring legacy will be to select and train an apprentice."

At this, Naruto went pale. He…a teacher? Naruto was a goofy chuunin and also a cold-blooded assassin. But working with a young child? Teaching?

"Are you sure I shouldn't kill another Kage?" Naruto asked, only half in jest.

"I failed twice before I found you, Naruto. This will be a challenge and the tests may kill your pupils. But you must persevere and must train up a Legendary Assassin to succeed you."

"I understand," Naruto said. "I suppose this is why you made me compile a library of scrolls, then, to train the next generation?"

"It will help."

Naruto knew how to plan an assassination. He knew where to start; how to probe for weaknesses; how to make the thing come off flawlessly. But to train a child? Naruto had been four when he began learning. How would he even meet four-year-old orphans to evaluate them?

"I will take up this challenge, then."

He had, too. He had selected one young child two years ago, but she had failed in her first assignment and had died.

Naruto had picked badly and his charge had suffered the ultimate penalty. How to do better?

Naruto, of course, already knew the answer. He couldn't just meet a single child and decide if he or she was right. He had to meet a lot of children…to weigh them all against each other and against a more absolute standard.

Naruto hated the idea…but knew it was necessary. Starting tomorrow, he would begin teaching at the Konoha Ninja Academy. He would see the youngsters. He would travel, from time to time, to the villages in Fire Country to scout for other likely candidates.

All the while he was searching for a true apprentice, someone who could succeed him and surpass him as an assassin.

Naruto closed his eyes and went to sleep. He would have a dire challenge starting tomorrow. Children.

The future.

Finding and molding the next generation's Legendary Assassin. It was as hard a task as Naruto's sensei had said. Blast that man.

Naruto wouldn't, couldn't, fail this final test.