The fastest sailboat is kind of the offset rig:

The fastest sailboat is kind of the offset rig:

I bet it's even faster if you reduce the weight by combining it with the deckhand obliterator!
Could the keel rig work in principle?
Since sailing requires you to push against something (the water) if that same something is the thing blowing in your sails it will just push you without really giving you much control. Instead if the currenents are a lot stronger deeper down it might work but then there's nothing keeping the sail downright(?) meaning without a comparatively heavy (because water is heavy) weight at the bottom of your sail you will likely capsize or more likely just be at an angle where you're not accelerating much.
Overall it seems at the very least impractical.
I think the only similar thing that would work is shooting a sea anchor in the direction you want to go from a deck gun, then pulling it back in.
I think you just invented the paddle!
Yes but it's an American paddle. With guns.
We could call it a Yank!
I can't quite identify the point at which this turns from real to parody
Schooner is the last real one I think.
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