On the battlefield, Third ninja war.

Jiraiya sighed and fiddled with the bandages on his arm, trying in vain to get rid of the itch around his wound. He looked up at the sky trying to ignore the dead bodies of his comrades and fellow ninjas strewn over the field. He hadn't seen Tsunade or Orochimaru in a while. But he wasn't too worried about them. They could handle themselves.

He turned around as he heard the sound of tiny uneven footfalls. His eyes widened as he saw a young boy barely four, walking on the battlefield and looking at the corpses in a mixture of curiosity, horror and disgust.

"Oi gaki, what are you doing here?" Jiraya asked in concern as he landed in front of the boy. He frowned in confusion as he noticed the trademark Uchiha looks, defined facial features and sharp black eyes. Why was he here? The boy looked up at him, eyes filled with raw emotion that shook Jiraiya to his core. He held out his hand and said "Come on! Let's get you away from here…"

The boy hesitated and furrowed his eyebrows in confusion but he dutifully reached out to the man's hand. Jiraiya smiled a little and then lifted the boy off his feet causing the little boy to gasp in surprise. It would be faster to get the boy out of there that way. Jiraiya pushed the boy's head down as tiny fingers dug in to his jacket desperately. He shouldn't see any more of this.

"Now to find your mother and give her a piece of my mind!" Jiraiya mumbled as he tightened his hold on the trembling boy and ran towards one of the tents at the campsite.

Konoha gates, After the Kyuubi's defeat.

Jiraiya wiped an eye as he looked out of the village gates. They had their victory but the price had been too high. He patted the scroll on his back gently, the one he had hoped to pass on to his student in due time. He headed down and turned his back to the Hokage mountain intent on leaving. He finally understood Tsunade's need to be away from the village that had claimed someone precious.

He had barely raised his foot when a soft voice, hardly a whisper, invaded his buzzing thoughts. "Where are you going?"

Jiraiya's white hair whipped wildly as he turned around in surprise to find a young child looking up at him. Even without looking for the clan insignia, he knew he was talking to an Uchiha. And more specifically he was talking to the kid he had taken away from the battlefield hardly a year ago. Black eyes watched him solemnly.

He sighed softly and bent down. "Aren't you supposed to be with your mother? I thought I told her to take better care of you."

"She's busy," the boy said calmly. "My little brother was making a fuss."

Jiraiya tried to remember when the newest Uchiha had been born but found that he didn't really care about it one way or the other. "Well then shouldn't you be making sure that he's alright? That is your job as an older brother, you know."

"My… job?" The boy asked, head tilted to the side as he looked up at the man.

"Yeah, to protect him while he grows up," Jiraiya said softly as he tried to ignore the image of his student and wife naming him godfather of their unborn child.

"Why?" The boy asked simply.

Jiraiya paused. Why? Why was it important to watch over some snot nosed kid anyway? His eyes caught a glimpse of the stone face of the fourth on the Hokage mountain. His student. He smiled bitterly, "Because he'll grow up to protect this village... our home."

The boy looked up at him, confusion etched over his face, but he was unwilling to ask the older man anything. Instead he reached into his pocket and then held his hand out to the older man.

"For when you get hungry on your trip." The boy stated simply as he held his hand open to the older man. Jiraiya looked at the pocky stick in the boy's hand but took it dutifully. Before he could say anything the boy had already turned away.

Somewhere near a hot springs, Konoha, Few years after Kyuubi's defeat

Jiraiya let out a perverted giggle as he spied on the women in the hot springs. His muscles tensed as he felt someone in the near vicinity. But he shrugged it off and continued spying on the women in front if him. Finally letting out an irritated huff he ground out, "What is it then?"

When no reply came he turned around and found himself staring at a curiously familiar face. Aristocratic features with long black hair framing fathomless black eyes. The boy cocked his head to the side as he stared at the white haired man.

"You shouldn't do that!" The boy said after a long silence.

Jiraiya smiled in amusement at the boy's expression. His face was carefully masked for someone his age, but his eyes betrayed him. Disapproval along with a hint of recognition shone through the carefully crafted mask. Jiraiya leaned back, mid-squat, and said, "What's it to you, kid?"

The boy remained silent before he took out some kunai and threw them. Jiraiya vanished in a poof of smoke leaving behind an old wooden log.

"Not bad." Jiraiya's voice came through.

Itachi turned around and came face to face with the man.

Jiraiya leaned forward and patted the boy's head. "You still need to work on your speed. But for your age, that's pretty impressive."

The boy ducked his head in embarrassment. "Otou- sama says it's nothing impressive." He glanced back up to see the white haired man frowning.

"Follow me kid."

Itachi stumbled at the tone but followed the man out of the hot springs and to one of the training grounds. He recognized the stone cenotaph for the fallen and idly wondered if any Uchiha were carved onto the stone. Grass crunched under his sandals as he followed the man to the logs on the other side of the clearing.

"Let me tell you something, kid." the white haired man said as he looked at the stone with a somber expression, "Being the best does not make you a good ninja. It makes you an overconfident idiot"

Itachi looked at the man, intent on catching every word.

Jiraiya stared at the stone and said, "It's what you fight for, that makes you a good ninja."

"Don't train to get praised by people, don't learn to be acknowledged, do it to protect something important to you."

"Important? Like the village?" Itachi asked in confusion.

Jiraiya turned to him. "It depends on you. Everyone has different things that are important to them. What's important to you?"

Seeing the confused look on the Uchiha's face he smiled gently, "You still have time to figure it out for yourself. Don't worry, sometimes it takes ages to understand what is truly important to you as a ninja. And when you do it'll make you stronger."

Then he sighed softly, "I don't want to see your name on this stone or any other stone for as long as I live, you hear?"

Itachi looked up into the grey eyes framed by white bangs and nodded.

Jiraiya watched in amusement as the boy's face went through several subtle emotions. "What is it kid?"

"You never told me you were the Toad Sennin!" Itachi said indignantly even as he tried to mask his emotions.

"Oh? Must have slipped my mind." With a mischievous grin he said, "Let me introduce myself properly then. A brat shouldn't miss out on this."

Itachi watched in confusion as a large amount of smoke filled the space in front of him. His eyes widened as he caught sight of the respected ninja in a ridiculous pose with one foot propped on a large toad. "Mount Myoboku-Gama's Holy Master Sennin…"

Itachi blinked and turned away saying, "I'm going to train!" ignoring the background sputtering of indignation from the Toad Sennin.

Konoha, Pre-Uchiha massacre

Jiriaya sighed in relief as the wind ruffled his long white hair as he sat on the Yondaime's head with his feet dangling off the edge. Jiraiya waited patiently for the boy to show himself and wasn't disappointed when he heard the carefully muffled footfalls of someone walking towards him. No words were passed, but Jiraiya tilted his head taking in the ANBU armor. He was glad that the mask wasn't on.

"Congrats!" Jiraiya said indicating the armor with a slight flick of his eyes.

"My father is proud of me." The recently recruited ANBU member stated unnecessarily.

Jiraiya half-turned with a frown. "Isn't he always?"

The boy's gazed straight ahead, shoulders slightly bent as he sat near the white haired man. "Sasuke has mastered the Gokakyu no jutsu."

Jiraiya waited patiently for the boy to sort through his thoughts. Minutes rolled by and the slight howl of the wind was the only sound around the two.

"He's grown up. I …" the boy started but paused uncertainly. That made Jiraiya tense uncertainly. What could have made the Uchiha so out of his element?

"If you had to make a choice between the people you loved and the village, what would you choose?" The boy finally asked in a soft and hesitant voice.

Jiraiya frowned, once again wondering what was really bothering the Uchiha. He glanced at the rooftops of the village and took a deep breath. "The old man would have probably said some tripe about the village being your family and all that, so you couldn't possible love anything more than that… but," an image of a blonde with a wide smile threatened to make him choke in emotion. "But if I had a choice, I think I'd choose the people I loved."

He heard the boy beside him turn his head to him but he kept his own gaze steady to the village rooftops. "It may be selfish, but I'd choose the people I loved."

Letting out a deep sigh he continued, "But I'd also make sure that in someway that the people I chose to protect would protect the village for me. I may not love the village as much as the Third, but it is my home and I'll always feel the need to protect it somehow"

Jiriaya turned to meet the black eyes, "Do you understand?"

Itachi blinked but nodded his head slowly. "I have to go, my brother is probably kicking up a fuss with my mother since I should have been home hours ago."

Jiraiya looked up at the boy and said, "Take care, brat!"

Itachi looked back at the man, his eyes seemingly young and softer. But the emotion vanished as he put on his ANBU mask and turned away. Jiraiya watched him leave and turned back to the village. "Why do you always make us choose?"

Random motel, Outside of Konoha, After the sound/sand invasion.

Jiraiya shifted the dead weight of the woman on his shoulder and looked on the partially hidden face of the rouge Uchiha. Striking a ridiculous pose, Jiraiya exclaimed loudly, "Hah! You should know that such a cheap gengetsu would never work on me. I don't need women to be tricked into seeing my good qualities."

Sharingan eyes glanced at him and Jiraiya saw a flicker of something pass them before the face turned away. His eyes softened for a moment as an image from the past overlapped the present.

"Ero-sennin!" Naruto groaned out.

"Brat, don't call me that." Jiraiya paused as he heard a snicker from the long haired Uchiha. That's not possible, he's not the same boy I met in the fields that day. But even as he denied it he couldn't bring himself to attack the Uchiha. He kept his eyes firmly away from the red Sharingan. I just have to stay away from his eyes.

Jiraiya groaned in irritation as the younger Uchiha, that Sasuke kid, stood up and practically growled out that he was going to fight his brother. He felt a little vindictive pleasure when he saw Itachi kick the boy back to the end of the hallway. Serves the brat right for thinking about fighting someone stronger than him.

But his irritation gave way to anger as he watched Itachi beat Sasuke ruthlessly. Was he such a bad judge of character, first with Orochimaru and then with Itachi. Had he been so blind to the darkness growing in them that he never noticed them change until they had already left him and the village behind as missing nins.

A flicker of light across his vision made him look up at the boy he had known so little about. Inevitably his eyes met deadly red orbs.

He was mildly surprised when the world around him froze, except for the black haired teen in front of him. "Uchiha Madara." The boy stated.

Jiraiya frowned in confusion. "What?" He had expected torture and pain from the gengetsu. Definitely more pain.

He started to counter the gengetsu placed on him. "Uchiha Madara…kyuubi" were the only words he managed to catch as he threw off the odd passive genjutsu that had been placed on him.

Before he could give the words any thought, he caught sight of the two Akatsuki members running away. He flashed through a sequence of seals and summoned a toad's esophagus intent and confident on catching the Uchiha and his partner. His eyes widened as he felt the ground tremble with an explosion and ran to the end of the hallway.

Jiraiya sighed in annoyance at the gaping hole at the side where a few dangerous black flames flickered seductively in the sunlight. Madara, Jiraiya frowned, just what had that insufferable Uchiha brat, missing-nin Jiraiya corrected himself belatedly, been muttering about.

A/N: Just something I thought up after reading the recent chapters. They must have met each other sometimes and I think Jiraiya, while he may not have understood Itachi a whole lot, I think he would have had a part in shaping Itachi's thoughts. So I tried to capture that, snippets of possible times they could have met.