Calrissian, along with his wife Tendra, continued to manage Tendrando Arms following the war. His YVH droids played significant roles in the subsequent Dark Nest Crisis, Swarm War, and Second Galactic Civil War. During the latter conflict, Calrissian aided his friends Han and Leia Solo in their efforts against their son Jacen Solo, who had fallen to the dark side and become a Sith, until Calrissian was informed that Tendra was pregnant; he then spent the rest of the war with her. After the war's conclusion, Calrissian settled down with Tendra in a life of quiet luxury, managing Tendrando Arms and raising his son, Lando Calrissian, Junior. He was later contacted by Luke Skywalker for assistance during a mission to the Maw with Skywalker's Sith allies. Calrissian reluctantly agreed, and successfully carried out the mission. Afterward, he returned to Coruscant and warned the Jedi of not only the danger posed by the Sith, but also the hidden menace which Skywalker and the Sith were pursuing. To that end, he assisted in getting a large number of Jedi StealthX wing starfighters offworld to assist the Skywalkers.
Leaving the restored planet, Calrissian and Vuffi Raa entered hyperspace with a cargo hold full of the last Rafa life-crystals to leave the system, as the Sharu shut off all trade from the planet soon after his departure. This valuable cargo netted Calrissian nearly 250,000 credits. After returning to Nar Shaddaa, he bought a used-starship lot from a Duros. To his dismay, he discovered the business was expensive and difficult to run. He debated whether he should either sell it or keep running it when the Galactic Empire decided to send a fleet into the criminal-ridden system intent on destroying Nar Shaddaa. To fight the intruders, Calrissian donated his inventory of ships to his fellow outlaws. He and Vuffi Raa then piloted the Millennium Falcon deftly in the resulting Battle of Nar Shaddaa, flying alongside noted smugglers such as Salla Zend, Han Solo, and Mako Spince. The attack was diverted, but at its conclusion less than ten percent of his stock was still spaceworthy. As a result, Calrissian sold 90 percent ownership in what was left of his lot to a man named Roa at a loss.
Soon after, Calrissian encountered Lehesu, a young member of the space-dwelling, hyperjump-capable Oswaft species. Lehesu's curiosity had carried him from his home in the ThonBoka Nebula to a desolate part of the Centrality, where there were no deep space materials for him to ingest. The starving Oswaft came in contact with the Millennium Falcon, which Calrissian had brought out of hyperspace in deep space to recalibrate its engine. After several halting attempts at communication, Lehesu finally conveyed his need for sustenance. Calrissian emptied the contents of the ship's recyclers into space, which Lehesu eagerly gobbled up. The gambler and the droid then cobbled together a tank full of nutrients that Lehesu could carry with him, so that he could get home. Lehesu then rewarded them with synthesized gemstones.
After spending several months on Cloud City gambling at the fancy casinos there, Calrissian played a game of sabacc against the Baron Administrator of the facility, a man named Dominic Raynor, after his success at gambling had caught the eye of the administrator. Little did he know that Ymile, the consort of Dominic Raynor, had helped him win with a skifter disguised as a pendant, but when a thief tried to steal her pendant, Calrissian seized him and returned the pendant to her, dubbing her his \"Lady Luck.\" Calrissian quickly found himself in a very high stakes game, with millions of credits and his Cobra on the line, which he lost. However, this was revealed to be due to the actions of a furious enemy of Calrissian's, Barpotomous Drebble, who had planted a skifter in the deck to throw the game to Raynor, in a form of revenge on Calrissian for the gambler's winning large sums of money from Drebble. Raynor ordered Drebble removed, but refused to discount the game. Because an anonymous benefactor then advanced Calrissian five million credits, the gambler bet four million and his lot on Nar Shaddaa against Raynor's administrator's post, and won not only his ship back, but the whole game and became the new Baron Administrator of Cloud City. In doing so, he also had the aid of Ymile, who helped tilt the game toward Calrissian with her pendant even though she was with Raynor, since she wanted to leave and see the galaxy. The unknown benefactor turned out to be Cloud City's cyborg liaison, Lobot, who had obtained the credits from the pooled funds of thousands of Ugnaught workers, in order to ensure Raynor's departure. Though Calrissian's methods for taking the reins of the city were considered unorthodox, his new position was confirmed by a vote of both the governing bodies of Cloud City, which had done nothing to stop his game against Raynor. His actions in taking over the city garnered him considerable media attention in Cynabar's Infonet, which gave his takeover a full article.
Calrissian also focused his efforts on other areas besides running the Cloud City and attending high-profile social events; among these were zoning. By placing the higher-class hotels on the surface of the city and the seedier elements of the city on lower levels, he helped eliminate the threat of criminals preying on tourists. However, he did not fully remove some of the rowdier areas, feeling that as long as the individuals there kept to that location, they could be easily contained. He also allowed a separate policing division to be formed by the more lawless district of Port Town. This provided a responsible, accountable security force to be in place, but also one with more leniency than the Wing Guard and a tendency to look the other way on certain activities within Port Town. Calrissian also stepped in to arbitrate a series of turf wars between employees of Jabba the Hutt and a rival crimelord based on Cloud City, Wonn Ionstrike. Calrissian faced down another challenge when Port Town crimelord Sawthawne began raiding Bespin's tibanna refineries, operating from the abandoned mining colony of Tibannopolis. Calrissian managed to convince a group of adventurers into destroying Tibannopolis while the Wing Guard launched a diversionary assault. However, his Wing Guard commander, Flagesso, turned out to be in league with Sawthawne. During this time, Calrissian met Orrk, the Guildmaster of the metalsmiths on Vandelhelm and learned of their ways and customs.
Staging from Sullust, the fleet departed, bound for Endor. The Alliance knew that this fight would determine the fate of the war, as they were committing almost all of their military resources in this battle. Furthermore, the Emperor himself would be present on the space station, giving the Alliance an opportunity to strike at the Empire's leadership in addition to its military might. Rebel intelligence suggested that the weapons systems on the Death Star were not fully operational, making this the opportune time to strike.
Solo reached Vandelhelm successfully after picking up two Venerated Ones, children who were descendants of the discoverers of Vandelhelm and who were revered by the inhabitants of the mining planet. Unfortunately for Solo, he ran into Imperial entanglements, in the form of a treacherous guildmaster named Orrk and his ally Mordur, an Imperial admiral. Just as Solo thought everything was under control, Mordur tried to flee, using a barge fleet loaded with valuable metal as cover. Solo was unable to fire on Mordur's ship because the barges were slaved to Mordur's vessel and would fly themselves into the sun if the admiral's ship was destroyed. Instead, Solo boarded Mordur's ship and defeated the Imperial, but was unable to stop the fleet from continuing toward the star. Not in possession of the codes needed to override the Imperial commands, Solo began to believe that that the Falcon, his passengers, and the barge fleet were doomed.
During the pollution crisis, Calrissian allowed Luke Skywalker and Ken, the \"Jedi Prince,\" to stay in one of his residences on Cloud City, though he was too busy to spend much time with his friends. While Skywalker and the others were on Bespin, Zorba Desilijic Tiure, Jabba's father, demanded that Calrissian hand over the Holiday Towers Hotel and Casino to him. Zorba had owned the casino previously, and felt that it was still lawfully his. Eventually, the two reached a compromise, whereby they would play a game of sabacc for control of the entire Cloud City. Calrissian was confident of his chances, erroneously believing Zorba to be a poor player. Ultimately, the Hutt won the game; he had cheated, using his Hutt ability to see ultraviolet light while using a deck of secretly marked cards. Calrissian was forced to hand control of Cloud City to Zorba, and fled the planet.
Calrissian fully expected all New Republic personnel to die in the onslaught. Noticing that the New Republic forces were occupied with the thousands of TIEs before them, Shadowspawn used this as an opportunity to flee. A special chamber in the volcano, conditioned for journey into space and fitted with a hyperdrive, lifted off, and once it left the atmosphere, jumped into hyperspace. However, the tide would once again shift. Skywalker was able to touch the minds of the Melters, a very primitive and unique energy-based species that lived on Mindor and controlled the meltmassif. With his prompting, the Melters were able to make the meltmassif evaporate, killing Shadowspawn's soldiers and destroying Shadowspawn's escape vessel, presumably killing the warlord. The New Republic forces were then able to jump to hyperspace, escaping Mindor before the planet exploded due to excessive radiation. Shortly thereafter, Calrissian resigned his general's commission. After he departed from command, though, Calrissian found himself treated coldly by Ackbar for his refusal to continue in military service. 153554b96e