The first ever boss that Sly encounters in the entire Sly Cooper series, is none other than Raleigh. Raleigh is the first encountered member of the Fiendish Five, the evil team of villains who stole the Thievius Raccoonus in Sly 1. In fact, it was Raleigh himself who found the Thievius Raccoonus, and allowed for the different members of the Fiendish Five to divide the book amongst themselves.
Raleigh's origin story is unique, and not quite like the other beginnings of the other Fiendish Five members. Raleigh used to live the rich and privileged life, where he was pampered and catered too. Eventually, Raleigh became bored of living a wealthy life of privilege. He then turned to a life of crime, becoming a pirate and used his machine building talents to become a machinist.
Raleigh had a real passion for stealing from others, getting a thrill that he never felt when everything was handed to him on a silver platter. Combining this passion with his creative skills, made Raleigh a very dangerous foe. Raleigh was so skilled, that he built a machine that would hover over the oceans and create storms to wreck passing ships so that he could steal from them. This insatiable desire for stealing made Raleigh a very fitting opening villain for Cooper fans to face as they entered the great Sly Cooper franchise; as he was the first of many unique and interesting characters to cross paths with Sly and the Gang.