I decided to do 3 in 1

Captain Hook
Classic Disney version Captain Hook, one of the most famous Pirates in media. I had to find a Pokemon who had a distinct mustache to represent him and I decided who else but Kricketune

Risky Boots
Another Pirate who is the primary antagonist to a video Game Hero, Risky Boots from the series Shante the Half Genie Hero. Shante and Risky have more of a amiable relationship than other nemeses, sometimes more like rivals and occasionally have worked together. I decided to go with Dusknoir but slightly changed the proportions on her body to give her that feminine figure.

Davy Jones
Probably the most iconic and fan favorite villain of the Pirates of the Caribbean franchize. Since I did Jack and Barbossa it was only seemed natural that I also drew Davy Jones one of the best Pirate Villains of all time. I considered using Octillery or Grapploct but I decided to go with Tentacruel being the more intimidating pokemon with Tentacles and a large claw. "Cruel" definitely describes Davy Jones, plus if he's the Giant Tentacruel or Dynamax's himself, then he can also be his own Kraken!