Littledog began his Puzzle Pirates career in January of 2004 as Octupa of the Midnight Ocean. Octupa a few months later joined the crew Savage Squids under the leadership of Drjekyll. The Savage Squids soon founded the flag Booty Grabbers. Octupa stuck with the Booty Grabbers until May 2005, and participated in their victorious blockade at Guava Island.
The pirate Littledog was first introduced in June 2005 when Octupa moved over to the newly formed Cobalt Ocean for good. Littledog joined the crew Black Horizon soon after Drjekyll moved over to Cobalt under the pirate Bnavver and founded the crew. Littledog soon became a senior officer and later received the title of lord under the flag Hurricane. Littledog participated and helped prepare for the first blockade of Terra Island in August 2005. Despite the loss, Hurricane continued to set their sights on Terra, and eventually won the island a month later. During the fall of 2005 Littledog was put in a tough predicament when friends Charisma and Foilistc left Black Horizon and created the crew Imperial Pillagers. Littledog chose to stick with his long-time friend Bnavver despite the massive amount of friends moving to Foilistc's newly formed crew. Black Horizon was never the same for Littledog. After Hurricane lost Terra Island to Imperial Margarine in early 2006, Littledog left the game for an extended period of time. Littledog would sneak on every once awhile and participate in pillages and blockades, but did not begin to actively play until 3 years after his retirement from Puzzle Pirates. With news of Bnavver's return, Littledog decided to try the game out once again starting in early 2009. He once again became part of Black Horizon and spent around 6 months making poe and having a great time with old friends. But, due to certain additions to the game itself, Littledog was not enjoying the experience to the same degree as before. With news of a new ocean appearing with the absence of poker, Littledog decided it was time for a new chapter in his pirate career.
Crimson became Littledog's main ocean early July 2009. Littledog almost immediately found old friends Charisma and Foilistc, and soon joined their newly formed crew Imperial Pillagers. Littledog currently owns an ironworking stall on Lima Island, and runs pillages when he has the time.
As of fall 2010, Littledog has retired from Puzzle Pirates indefinitely. Due to the limitations of Crimson and its decline, Littledog does not feel as though the game has anymore to offer him. If you're interested in contacting Littledog simply PM him on the Puzzle Pirates forums, which he still checks on occasion. Littledog is also always looking for more people to play with on Xbox Live, so don't hesitate to PM him your gamertag as well.