Okay I wrote this under two assumptions.
1. Considering his personality I'm assuming that Kaito doesn't read serious news often. Mostly just the stuff that talks about his heists. So he might know Shinichi's name but not necessarily his face.
2. I only consider what is written in the Manga as canon. In other words Kaitou kid does not know about Conan/Shinichi connection. (He did mention during the miracle air walk case that people who snoop into other people's business were the truly rude ones. If he kept to that then he doesn't know.)
Anyways this is my first Fan-Fic be nice please. (I do not own Detective Conan) I'll try to keep the characters in well... character? Just to warn you this was ment to be a one shot.
Chapter 1 - Second Introduction
His lungs burned as soon as he inhaled the wintry air from the rooftop. He closed the door behind him and walked calmly across the surface. This last job had been entirely too easy. Nakamori-keibu was starting to slack apparently. Maybe it was time to add alittle fuel to the fire.
Filling his office with confetti had potential. It would take forever to clean up from every nook and cranny. He wouldn't forget something like that anytime soon. But that wouldn't really make the other task-force members motivated. Maybe if he sewed re-inflating whoop cushions into the existing cushions of the task-force's chairs? It would make office life for them entertaining for a couple of days at the very least.
Just thinking of the endless possibilities made Kaito's face split into his world famous grin. It was for his and Nakamori's own good after all. The old man needed the extra exercises. Wouldn't do to let him go the same direction as Meguire-keibu now would it? His health and detective abilities impart reflected how good a thief Kid was after all. Besides lack of motivation on his part would make Kaito's part boring. Silently going threw the list of things he would need for some of the tricks, Kaito chuckles to himself.
"Something funny Thief-san?" A voice piped up from the shadow of the wall infront of him. Kaito paused briefly at the words and the sound of the voice. Both were oddly familar to him. His face became completely calm almost like putting on a mask. The voice sounded almost like his own which was disturbing enough but what gave him chills was the simple sentence that was uttered. He had heard those words before.
"Just thinking of some 'greeting cards' I'm planning on preparing once I leave this place." Kid said as the owner of the voice slowly stepped out of the shadows into the moonlight and Kaito once again felt slightly disturbed. This person was almost a mirror image of his unmasked self. "I didn't think anyone would be up here this evening. What a pleasant surprise. I assume your a detective?"
"Humm... you could say that." His mirror image smirked slightly. It was unnerving to Kaito. It was almost like he knew something that he Kaito didn't. Was this how others felt when he grinned at them? "The recipients of those greeting cards have my sympathy by the way." The detective said.
Kaito chuckled slightly. "Could I ask how you managed to figure out I was headed here and not towards downtown?" He did actually want to know. Kid thought he released the dummy perfectly without anyone being the wiser. Reason he was still on the loose was simply because he kept track of his mistakes and learned from them. Just as his father had done before him.
The detective actually grinned. "Almost all the businesses downtown are closed this time of night and there are only a few people still there. Can't hide in a crowd when there is no crowd now can you? Besides it only takes a cheap set of binoculars to see the propeller on the dummy's hand-glider."
Rather pleased at the explanation Kid's grin becomes alittle more genuine. This Detective was merely a prepared one. Of coarse that meant he was at least a decently intelligent one. "We haven't been introduced Tantai-san. I like to keep track of the hounds on my trail. Could I have your name please?"
"I'm hurt Kid-san" the doppelganger gives him a sharp look with a smirk, "I know this is the first time we've met 'eye to eye' but to not even recognize your own Big brother."
Kaito's calm face cracks for a moment as he looks at the detective. Shock was very evident in his expression for that brief second. "Woah woah... wait a minute... Okay there is a way that's possible but dad was not that type of guy ... at least I don't think he was. This guy could also be saying that because I look like him but how the hell would he know I look like him??" Kaito takes a hardly noticeable breath. "Maybe he's fishing for information... playing mind games... okay have it his way. I'll bite."
Kid flashes his grin and says casually. "Hate to mention this tantei-san but I have no siblings."
Both of the detective's eyebrows rise and he looks closely at the thief. It seemed he was trying to detect a lie. A look of dawning understanding passes over his face. "You're not the original Kid are you?"
Kid's entire body jerks slightly. He was no longer even trying to keep up his grinning mask. "Did I miss something... wait a minute. Big brother... that's a term to sometimes describe over zealous governments or ... organizations. Was this guy part of the organization?" Kid's mouth flattens into a abnormally serious line and as quick as his nimble hands could, pulls out his card gun and aims it at the 'detective'. "It all makes sense. The organization's people are the only ones other then myself and Jii-san that know about Kid being Dad and his death. The Big brother thing was a test apparently and I failed." thought Kid in sudden realization.
Shinichi's eyes widen slightly as he stares down the barrel of Kid's card gun. Whatever happened to 'no-one gets hurt'? Kaitou narrows his eyes and says in a uncharacteristically frightening voice. "I have a few questions for you Tantei-san."
Shinichi opens his mouth to ask what they heck he was thinking when voices broke out below. "...one of the spotters saw him on the roof quickly men!!"
Officers bust threw the doors and Kaitou hisses in anger. Tossing something towards the ground the entire rooftop is instantly covered with thick smoke. "We WILL meet again Tantei-san."