The story starts off with a view of St. Canard and Darkwing narrating about
the audience seeing something completely different. He explains that
three hundred years ago there was another masked mallard that fought for
justice: Darkwing Doubloon.
The scene quickly changes to the high seas, where Seaman Drake
a.k.a. Darkwing Doubloon, is serving King Herb, Queen Binkie, and the
two princes Honker and Tank aboard their royal vessel (I'm sure he loves
that job).
One day, the royal vessel is spotted by the pirate Negaduck and
his fearsome crew, consisting of none other than Megavolt, Bushroot,
Liquidator and Quackerjack, who are now in pirate attire (except
for Quackerjack who has the same outfit for whatever reason). They
quickly take all the jewels from the ship and leave to divide up the goods.
Once the bad guys are gone, Drake tricks the Muddlefoots into abandoning
ship and changes into Darkwing Doubloon.
After a brief meeting with his crew, (Gosalyn, Launchpad,
Fenton/Gizmoduck and Stegmutt), he confronts Negaduck on his pirate
vessel before running back to the comandeered royal ship. Doubloon
then gathers his crew to fight Negaduck and the other pirates to get the
King's jewels back. Once on board Negaduck's ship, Gosalyn gives the
jewels to the others to take back to their ship, but is accidently locked
into a chest by Stegmutt. Doubloon and the others are defeated, but they
make off with the treasure, unaware that Gosalyn is still stuck on
Negaduck's ship.
It doesn't take Doubloon and the others long to realize that Gosalyn isn't
with them. In an attempt to get her off of Negaduck's ship, they give him
the jewels back. Not surprisingly, Negaduck refuses to hand her over after
the jewels are returned to him. Furious, Doubloon plots to let Negaduck
think that he's sinking their ship, so that he can slip on to their pirate vessel
and get Gosalyn back.The plan is unhinged when Quackerjack and Bushroot
tie Gosalyn to the mast and attempt to ram their enemy's "sinking" ship.
Stegmutt cannonballs Doubloon onto Negaduck's ship and he
rescues Gosalyn from the mast. Unfortunately, Negaduck's ships rams
through the center of Doubloon's vessel and sinks it, leaving all the
heroes stranded in the water.Depressed and angry at being bested, Doubloon
is pleasantly surprised when Gosalyn reveals that she stole a map
from Negaduck's cabin that will lead them straight to the pirate's hideout.
They sail Stegmutt to the island, where the crew captures the four pirates
and Doubloon beats Negaduck. Afterwards, the five pirates are tied up
and left in a compartment aboard the Muddlefoot's new ship.
Seaman Drake returns the jewels to King Herb, who grants him one
piece of gold to keep for himself. The episode ends with Drake sailing
the new royal vessel into the sunset.