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Both pre-Flashpoint versions.

Which Rogue captain wins?

C'moooooon!

I'm almost 100% sure that the reason why you haven't gotten any replies yet is because Captain Cold WRECKS Captain Boomerang.

I'm going with Captain Cold especially after Bentley told me some of the "cool" stuff he can do.

Wreck? I'm not so sure, especially not after Digger got his Brightest Day upgrade.