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Pash Cracken was a Human male career starfighter pilot who throughout his life served in the Rebel Alliance, the New Republic, and the Galactic Alliance. Born on the planet Contruum around the year 20 BBY, he was taught both morality and starfighter combat by his father, Airen, whom he followed into the Rebel Alliance during his teenage years. Cracken enrolled at the Galactic Empire's Vensenor Flight Academy under a false identity to hone his skills, and after graduating, he led an entire wing of TIE fighter pilots in defecting to the Alliance. The members of the newly-dubbed Cracken's Flight Group were assigned A-wing fighters and given patrol duty at an Alliance base on the planet Xyquine II, which was eventually abandoned when the Empire attacked. During the evacuation, Cracken ordered all personnel to subtract the number two from their assigned hyperspace coordinates, and then led his flight group in destroying the Victory-class Star Destroyer Exsanguinator. The former maneuver shook the pursuit of eavesdropping Imperials and became famously known as the "Cracken Twist;" both maneuvers turned Cracken into a legend.

When the Alliance became the New Republic, the pilots of Cracken's Flight Group began to view their leader as an invincible hero, and Cracken requested a transfer to the legendary Rogue Squadron in 7 ABY so that he might reassess his skills. One of his first missions with the Rogues was a covert insertion onto the Empire's capital world of Coruscant in order to gather intelligence prior to a New Republic siege of the planet. Cracken flew a Z-95 Headhunter when the Rogues disabled Coruscant's planetary shields, and the New Republic successfully captured the world. Rogue Squadron spent the subsequent weeks obtaining bacta in order to combat the deadly Krytos virus left on-world by the departing Imperials; after a cure was developed, all the Rogues save for Cracken resigned their commissions and initiated a guerrilla war against former Imperial Head of State Ysanne Isard. Cracken remained with the New Republic due to his father's role as Director of Intelligence, but he lent Rogue Leader Wedge Antilles aid and led an A-wing squadron into the battle that toppled Isard. Two years later, he flew against the forces of the Empire's Grand Admiral Thrawn.

In 28 ABY, Cracken commanded the Interdictor cruiser Memory of Ithor in the war effort of the Galactic Alliance&mdash;the New Republic's successor state&mdash;against the extra-galactic Yuuzhan Vong. The cruiser was destroyed during a strike at the Yuuzhan Vong–held Bilbringi Shipyards, and Cracken and the surviving crew were taken prisoner on the planet Selvaris. While incarcerated, Cracken and the legendary commando Judder Page received vital information from the intelligence-gathering Ryn Network and arranged for four prisoners to escape and deliver it to Galactic Alliance High Command. Their efforts allowed a Galactic Alliance strike force to rescue them, but two subsequent battles brought Cracken to Caluula Station, where he was again captured and taken to enemy-occupied Coruscant. There, a group of heretical Yuuzhan Vong Shamed Ones rescued him from being sacrificed to the Yuuzhan Vong gods. The Galactic Alliance soon thereafter struck at the capital, and Cracken was rescued and recruited into Page's Katarn Commandos as they stormed the citadel of the Yuuzhan Vong's Supreme Overlord Shimrra. They secured the fortress, which allowed Jedi Master Luke Skywalker to kill Shimrra and bring the war to an end.