The earliest reliable accounts possessed by Galactic Alliance historian Voren Na'al of his life dated to 4 BBY, when Calrissian was around the age of twenty-seven. Already a professional gambler,[19] Calrissian won a battered YT-1300 freighter called the Millennium Falcon in a high stakes game of sabacc on Bespin from a man named Cix Trouvee, who was also a gambler. Calrissian won with an Idiot's Array, the best possible hand in sabacc, leaving Trouvee destitute, though the other man went on to do well for himself, eventually becoming a partner in a successful resort company.[12] As he had no piloting experience, Calrissian sought out a Corellian smuggler and skilled pilot by the name of Han Solo, in hopes of being tutored in flying by Solo.[19] Calrissian found Solo on Nar Shadaa being held at gunpoint by the bounty hunter Boba Fett, who had drugged Solo in preparation for collecting the bounty on the Corellian. Calrissian caught Fett by surprise, however, and drugged the bounty hunter with the obedience drug that had been used on Solo, after administering the antidote to Solo. Solo and Calrissian then ordered the entirely complacent Fett to disarm himself and fly his ship off to unknown space. Afterward, Solo eagerly taught Calrissian the basics of starship piloting. For some time, Calrissian flew several various smuggling runs,[28] sometimes partnered with smuggler Salla Zend.[29] Calrissian eventually parted ways with Zend and used his new piloting knowledge to fly the Falcon to the Centrality.[28]
Following the events involving Thune, Calrissian took his job as Baron Administrator seriously, even becoming a legal citizen after taking office,[54] and worked closely with Lobot for over two years,[55] though he considered running Cloud City the strangest scam he'd ever run.[56] During this time, Calrissian became known as a capable steward of Cloud City dividing his time between various conferences with the Parliament of Guilds, reviewing possible trade routes and agreements, and making appearances to Cloud City's citizens. Likewise, Calrissian meet with the city's corporate administrators, known as the Exex, and received their various reports, outlining their needs and wants, from the numerous corporate liaisons; acting on these reports, Calrissian did his best to comply with their requests and kept the number of diverse businesses within Cloud City content. With the title of Administrator, Calrissian was also responsible for being judge in a number of legal disputes for people, or crimes, that were not brought before a tribunal of the Parliament of Guilds. Among Cloud City's denizens, it was well known that Calrissian would arrive at his legal decisions by using the confidential advice of Lobot, his computer liaison officer.[54] Over the years, Calrissian and Lobot developed a nonverbal communication system which allowed them to send subtle messages to each other.[57] The new Baron Administrator also started wearing an easily concealed wrist-comlink that could interface with the Cloud City Central Computer, as well as allowing him to direct his subordinates.[58]
While Skywalker and Solo were busy tracking down the Minstrel, Calrissian and Chewbacca found themselves in dire straits in the streets of Stenos. Believing that Drebble had ordered them to be killed, the pair participated in a running firefight with a large group of Drebble's gang. Nevertheless, Calrissian expressed surprise when Drebble appeared and ordered his gang members to cease fire, explaining that the former gambler and Chewbacca were actually old friends of his from the Rebellion. Believing that Drebble had changed for the best, due to his newfound stature brought upon by none other than himself, Calrissian explained to Drebble why he and Chewbacca had sought him out. Though Drebble was visibly sad to give his "award" back to Calrissian, he was cheered when Calrissian told him that they were friends, and that he furthermore had truly earned the friendship of the Alliance. With the Dancing Goddess in their possession, Calrissian and Chewbacca then hastily made their way back to Godo.[132]
When Calrissian next encountered Solo again on Coruscant, Mara Jade was also present, and Calrissian found himself attracted to the former Imperial assassin; however, Jade coldly rebuffed his charms, leaving him to contemplate how to best attract her attentions. While Calrissian was making repairs to the Falcon, Solo arrived in the hangar bay, demanding passage to Mon Calamari to rescue Leia, as the world had fallen under attack from Daala. Calrissian agreed, but insisted on flying. En route, the gambler suggested playing sabacc for the Millennium Falcon again. Solo agreed, and this time the Corellian won the vessel back from Calrissian. The pair arrived at Calamari, and Solo was able to rescue his wife, returning her to Coruscant.[159]
When the Glorious and its escort first approached the unknown vessel[23] in the Inner Rim[167] Gmar Askilon system, Calrissian was initially annoyed at Pakkpekatt's cautious approach, as twenty-two days passed without their team attempting to make contact with the vessel. Eventually, an unmanned ferret was sent in closer to the vagabond to investigate. As it did so, the vagabond sent out a melodic communication pulse and then jumped to hyperspace after it received no response. Calrissian asked Threepio to analyze the transmission, but while the sound was similar to one that had been recorded as coming from the vagabond earlier, it did not exist within the protocol droid's databases, nor any other. Thanks to an interdiction field established by Pakkpekatt, the vagabond did not jump a great distance, and while the fleet closed to their usual following distances, Calrissian and Pakkpekatt disagreed over the best way to approach the vessel. Pakkpekatt sought to launch boarding teams to investigate the alien craft, while Calrissian felt that more time and caution was needed before approaching the vagabond.[23]
There, Solo and Calrissian reclaimed their ships, though Calrissian was outraged by the damage done to his ship. As they were repairing the Lady Luck, a number of droids that had been stolen from various New Republic sources exploded, as they had been built as part of a plan to sabotage droids and computers across the New Republic. The droids had been stolen by various smugglers and now their confiscation came back to haunt them when their illicitly acquired property killed and maimed many of them. Solo and Calrissian, despite the fact that many of the denizens of Smuggler's Run had betrayed and treated them badly, did their best to provide aid. In fact, Blue had lured both Solo and Calrissian there so the mastermind behind the droid sabotage plot could capture Solo to use as leverage against Leia and Luke Skywalker and thus damage the New Republic. Nevertheless, Solo and Calrissian opened up their vessels to ferry the injured to Wrea, the nearest inhabited world with the medical capacity to treat the numerous casualties.[37]
He was also quite proud of his charm on females, and was known to exercise it, particularly in his younger days, before he eventually fell in love with and married Tendra Risant.[38][36][49][17] He was also an author; by the time of the Yuuzhan Vong War he had written and published two memoirs, A Toss of the Dice: This Gambler's Life[200] and How to Succeed in Everything (22 ABY); this second memoir was a bestseller.[201]
Calrissian's second ship was the Millennium Falcon, a battered YT-1300 freighter which was eventually made famous by the exploits of Han Solo. Having joined a high stakes sabacc game, Calrissian found himself betting against a fellow gambler by the name of Cix Trouvee, the then-current owner of the Falcon. Through a turn of fate, Calrissian managed to get the Idiot's Array, the best hand possible in sabacc, and won the Falcon from Trouvee.[12] Calrissian also modified the freighter by adding quad laser cannon to the ship as part of an armament upgrade.[203] However, even though he was extremely happy at his good fortune, Calrissian soon remembered that he had absolutely no experience flying anything, let alone a starship the likes of the Falcon. To remedy this problem, Calrissian sought out the services of a young pilot by the name of Han Solo who had recently started to make a name for himself as a smuggler working out of Nar Shaddaa. Agreeing to help him, Solo taught Calrissian how to fly the Falcon. Using his newly acquired talents, Calrissian set out for the Centrality, an independent government consisting of several dozen star systems.[28]
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