Excuse my newbie-ness if this has been asked before, but there was no such thing as the internet when I was nine years old...
I've been a fan of the Pirates line since they first went on sale, but right from the start I wondered why the pirates themselves seemed to have the biggest and most impressive ships while the 'good guys' seemed to use vessels that were, well, smaller. The Pirates II line seems to be an exception to this, but in the 90s at least there were huge ships like the classic Black Seas Barracuda and Skull Eye Schooner (confusingly, they were given different names in the UK, but I digress...) while the Caribbean Clipper, Imperial Flagship and Armada Flagship were single-masted and had much smaller crews. The Renegade Runner and the Cross Bone Clipper are the only pirate ships that I can find that were actually smaller than those of the 'Imperial' side!
I never did understand why. I assumed that the pirates were independent renegades who sailed around looking for treasure and causing mischief while the 'Imperial' fleet were supposed to keep order. Even as a kid I wondered whether the pirates would've preferred smaller ships that were easier to hide, and why the Imperial commanders didn't use bigger ships to make a statement and match the size of the pirates'.
I'm not sure if it's Nostalgia Goggles at work here, but Brickbeard's Bounty and the Imperial Flagship don't seem to have the charm of the old ones. I owned the CC in my childhood, but when I realised my dream many years later to own the BSB to go with it, I thought that the CC still isn't as cool!