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Okay, this is one of the best theories I've heard so far, but there's a problem. Remember what Leon said in KH? The Keyblade chooses its master so I doubt Terra could do it for Riku.
Do you know the linger sentiment he was talking to sora and said something along these lines "your not the one i chosen" and we know that riku was a chosen wielder so Terra chose riku to be a wielder.
terra watches young sora and riku playing swords in the playground island.
Also it doesnt mean that Terra was on destiny island the same time Aqua and Ven where there.