This is a painting by Jack Horner of the famous Deep Reaver.
In 1877 The Deep Reaver came back to town with a strange whale. It had rows of black eyes, and it's flippers were more like tentacles. The fortunes made from sell the parts of this whale went to help found Brindlewood Bay.
Most modern scholars believe that it is an old wives' tale or the Deep Reaver had managed to pull in a Sperm whale that was attempting to eat a giant squid. There is a small amount of tourism based around "Biggie".
The Deep Reaver was eventually lost at sea several years later.