Sky Pilot is a member of the O.S.I. agents' group who once went rogue and joined the newly revived agency of SPHINX. It is revealed in the Season Four finale "Operation P.R.O.M.", that he was actually a mole implanted in SPHINX by the OSI. Following these events, he officially rejoins the OSI under the command of the new General, Hunter Gathers.
Sky Pilot, formerly known as Mile High was agent for the OSI until he was forced to leave, after a "don't ask, don't tell" beef incident. He later went rogue and took on the name Sky Pilot and along with his "partner" Shore Leave (formerly Holy Diver) and began non-violence youth ministry in southern California. It later turns out that this was merely a cover as the two were later revealed to have join the newly revived agency of SPHINX under the command Hunter Gathers.
He first appears in the "The Family That Slays Together, Stays Together (Part I)" where he along with Shore Leave are asked by the visiting Brock Samson who is on the run from assassins and needs to get the Venture family to Spider Skull Island where they would be safe. Unfortunately, the duo refuse to use violence but protect the Ventures as Brock is attacked by the assassin Go-Fish.
At the end of the episode "Blood of the Father, Heart of Steel" he appears along with Hunter Gathers at the headquarters of the newly revived agency of SPHINX.
In "Operation P.R.O.M.", he is shown mostly with Gathers as they guard Monstroso later and are captured by the OSI. Near the end of the episode, it is revealed that Sky Pilot is actually a mole implanted in SPHINX by General Triester. It is also revealed that the "Monstroso" they were guarding was actually a fake which contained SPHINX agents who along with Sky Pilot take Doe and Cardholder into custody when it is stated they are Guild mole agents who tried to cover their tracks.
Sky Pilot with the rest of the SPHINX agents soon return to work for the OSI once Gathers is given control over the agency by Triester.