During the late period of World War II, the Losers were assigned in rescuing an O.S.S. squad led by Colonel Richard Flagg who were escorting German scientist Dieter Teschner from Dinosaur Island during Operation Four Horsemen. Once they got on the island, one by one, they are killed due to the dangers of the island: Gunner was crushed by a Tyrannosaurus rex, Storm was snatched by pterodactyls, and Sarge by being "side tracked" from avenging Gunner's death.

Pooch and Johnny Cloud eventually discovered Richard Flagg as the only survivor of his squad. Flagg was forced to escape the island alone, as Cloud and Pooch decided to stay and kill the dinosaur that was responsible for Gunner's and Sarge's deaths. However, Pooch was accidentally killed in one of Flagg's booby traps and Cloud was also wounded. As the last Loser, Cloud was able to kill the T-Rex in which he sacrificed himself by allowing himself to be swallow whole while primed with two live grenades.

Before his death Cloud made an epitaph, of sorts, dedicating to his team: "Ask my family and they'll tell you I was a Navajo. Ask the Army Air Force and they'll say I was an American. But if you ask my brothers, they'll set you straight. John Cloud was a Loser."

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