Sky Shadow comes to us as an homage to Black Shadow from the Japanese continuation of G1 in the Victory series. The figure uses the body of the Generations line’s Thunderwing with a new re-tooled head.
In the Victory series, (Black)Sky Shadow was that of a gangster/mercenary skilled in robbery, extortion, and murder who would sell his service to whoever could pay his price in energon. Even the Decpticons hated working with him as they couldn't be sure that he would sell out to higher pay mid-job.
In the Trans-Tech fanfic, using the Black Shadow nomenclature, Sky Shadow was hired to assassinate Gutcruncher. Using his stealth technology and an excellent position, Sky Shadow was able to not only assassinate his target, but frame 2 Autobots for the assassination in the process; Jackpot and Hubcap. Unfortunately for Sky Shadow, his ego got the best of him. In true villain fashion, he monologued his entire plan to Hubcap, whose primary function just happens to be communications. As a crowd formed, Hubcap broadcast Sky Shadows bragging to all around. Dirge and Gigation resident, Menasor, who happened to be cohorts of Gutcruncher, overheard everything and made short work of Sky Shadow. Sky Shadow’s head and therefore datatrax about the assassination have yet to be recovered.