(also by @/luuuna-rambles tumblr's gif search is a nightmare)
Ed, the greatest pirate captain of all time:
And then of course we have Stede who wanted to be captain so bad he paid his way in
And Izzy who wanted to be captain so bad that the only way to placate him was to promise he could be captain and who had a tantrum when Ed didn't kill Stede in order to retire and leave Izzy the captaincy like he said he was going to, a tantrum which lasted 4 episodes and almost got stede killed twice and everyone involved killed once: