@Ninjabrownie:
I'll give you something more plausible than Kuma being a revolutionary. He's a pirate. And a smart one. So he's in a position of power.
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He gained respect for Luffy because of how they protected him, especially Zoro. Kuma once had (was part of) a crew himself, being a pirate and all. So far, apart from the scum Kuro, bonds between crewmembers are a serious aspect of respect between strong, revered pirates.
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His life does not revolve around analyzing Luffy and Hancock. He does the Shichibukai thing. Balance of power between them, the Yonkou and the WG, remember? Now, the WG is luring the strongest Yonkou in and wants to have the Shichibukai do war with them. 2 down, 1 up. The WG will stand stronger, relatively, if the war went along these lines. The Shichibukai and the Yonkou considerably weaker. This is a stretch, but perhaps Kuma protected the SH's from being captured because he sees potential in them. Future Yonkou material.
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Just to point out he's concerned about power matters, after he told Moria that Crocodile had been replaced by Blackbeard, he says something to the effect of the balance of power crumbling.
So where this goes is up to Oda. But for a smart pirate, it 'appears it would be wise' to turn against the WG at this point.
And whether Dragon shows up or not, part of his forces are already fighting for Ace. I hope he joins as well. Sink the entire Marine fleet with a tornado. Man, with all those overpowered fighters, how the hell are they going to keep their ships intact?!
I like the idea of Kuma being another of those resurrected ancient weapons. They probably synthed the tech for having objects eat devil fruits and making pacifistas from him after they found out that he wasn't a machine that obeyed orders without question. It would make sense if he was a revolutionary then as after being around when the WG first took over during the void time he would want to stop them. I dont think they ever actually gave info on what kind of pirate kuma was before did they? ( I could be wrong here ) still its an interesting theory.