Wingman was the alter ego of Jeff Winger. He existed in a G.I. JOE™ themed reality imagined by Jeff when he fell into a coma. Wingman lead a squad of troops which became known as the "G.I. JOE™ Mutineers" and piloted the Wingjet jetpack. Jeff was torn between losing himself in this cartoon fantasy or returning to reality and accepting a truth he was trying to forget. Wingman's first appearance was in the Season Five episode "G.I. Jeff".
A peaceful day in the country of India was disturbed when the forces of the terrorist organization known as COBRA™ converged on the Taj Mahal. Ground troops commanded by the villainous Destro marched towards the target while he approached from the sky leading a squadron of Rattler's. Destro ordered his soldiers to attack and launched a missile at the palace. It was unexpectedly intercepted by a rocket fired by the just arrived G.I. JOE™ Team. Assigned to this mission was Wingman and his squad Tight Ship, Buzzkill and Three Kids. As he provided air support using the Wingjet™ pack, his team was on the ground engaging the enemy troops. He flew down to reprimand them for disrespecting the CO Flint and not being focused on the battle.
Buzzkill challenged Wingman to show them how it was done and he did so by taking out Destro's Rattler. Flint complimented his shooting but pointed out that Destro safely ejected and was escaping. Wingman then shot holes in his parachute which caused Destro to plummet to the ground and die. The other Joes were shocked by what happened ignoring Wingman as he celebrated by shouting "Yo Joe!". In the aftermath, Wingman and his squad was charged with violence, mature language and conduct unbecoming of a G.I. JOE™. When they returned to base they were all brought before a tribunal to answer those charges. Wingman defended himself by saying if they couldn't kill the enemy they might as well start killing themselves.
The tribunal was not persuaded and locked Wingman and his squad in the brig. They found themselves with other G.I. JOE™ rejects including a Joe code named "Fourth Wall". On a recent mission to a COBRA™ excavation site, Fourth Wall's perception of reality changed. He now believed they all inhabited a children's syndicated cartoon which was connected to a higher plane of existence. Wingman mocked his idea but somehow recognized the enemy code name for the site Fourth Wall infiltrated which was "Greendale". Wingman felt a panic attack occur at its mention and also when Fourth Wall showed him an artifact he brought back; an action figure of Duke. That toy, along with hearing the word "Greendale" once more, caused Wingman to collapse.
In his unconscious state he imagined himself in a children's toy commercial for G.I. JOE™. He also saw a brief glimpse of another reality where he was in a hospital room surrounded by analogues of his squad. Upon awakening, Fourth Wall suggested Wingman's reaction to his theory meant he had some connection to the higher reality. Wingman refused to believe it even after he heard his squad call him "Jeff" and speaking as though they were the people he saw in the other reality. As he tried to process this, the G.I. JOE™ base came under attack. The forces of COBRA™, this time led by Cobra Commander, were retaliating in response to Destro's death. The wall of the brig was destroyed by a stray missile freeing Wingman and his squad.
Once they acquired weapons, Wingman hoped that by defending the base they would redeem themselves. Unfortunately his attempt at laying down suppressive fire killed several COBRA™ troopers and the G.I. JOE™ codenamed "Lifeline". Duke and Flint begin shooting at Wingman and his squad who boarded a "Submachopter" and flew away. Wingman criticized himself for what happened and wondered aloud how things had come to this. Fourth Wall suggested "Greendale" might have answers to that question and the word triggered another reaction in Wingman who passed out. He saw a different toy commercial along with a brief glimpse of the squads counterparts. Upon awakening, he resolved to go to Greendale only to be informed by Fourth Wall that the Submachopter was already on its way there.
Upon arrival, Wingman and his squad easily overpowered the COBRA™ security guards and made their way into the excavation site. Once inside they found what appeared to be a school which seemed somehow familiar to them all. After they entered the building, they were intercepted by a trio of COBRA™ officers who were codenamed Overkill, Xim Xam and Major Dick. Wingman took out Overkill and Xim Xam by shooting them in the shin while Major Dick incapacitated himself while trying to attack them. The squad makes it to the study room and Wingman was able to remember that he was actually of Jeff Winger. He also recalled who his squad was all in real life. This included the Vice Assistant Cobra Commander (Dean Pelton) who was overjoyed to see him. Wingman headed to the cartoon realities version of Jeff's office and found the reason behind his current situation.
He returned to the study room and confessed that in reality his depression over his fortieth birthday caused him to drink a fifth of scotch and down some Korean youth pills. Fourth Wall told Wingman he could return to the real world but he preferred to live in this fantasy. They were interrupted by the united COBRA™ and G.I. JOE™ forces of "JOEBRA". Wingman at first convinced them he wanted to stay in this world but changed his mind when he discovered cartoons couldn't indulge in adult pleasures. After a quick brawl back to the study room, he donned his Wingjet pack and flew to the barrier separating realities. Cobra Commander grabbed on but failed to survive the trip between worlds. Jeff awoke in his hospital bed surrounded by his friends. He admitted why he ended up in the hospital but they didn't care and were just happy to have him back ("G.I. Jeff").