Shay Cormac and the Morrigan vs. Edward Kenway and the Jackdaw vs. Connor Kenway and whatever his ship is called

Probably Shay.

Edward.

Poll = bulleted list, lol.

I haven't played AC: Rogue yet, but I think I'd say Connor or Edward anyway. Edward is by far the better sailor, but Connor has tech advantage. The Aquilla has mortars and stuff right off the bat, even if all the ships are fully upgraded, Connor has the ship with the most potential...

That is if I'm remembering this correctly. The Aquilla has mortars, right? If yes, I think Connor barely takes it. If not, I think Edward takes this easily.

Edward is the more skilled captain

I've played all 3 and I believe Shay would win. Has a higher technical advantage than Connor and a better fighter than Edward. I say this because I was able to beat 4 legendary battles without fully upgrading my ship, these battles included numerous brings, frigates, and a couple of man o' wars. He also has more experience with Templar and assassin fighting techniques than Edward. Edward's just a pirate who just so happen to stumble upon the world of assassins and Templars.

A fully upgraded Jackdaw can destroy Morrigan and Aquila.