Ambush in Cloud City This ambush was set up by the bounty hunter Bossk in 1 ABY in order to capture Baron Administrator Lando Calrissian , who had come into possession of Cloud City by winning it from Dominic Raynor in a game of sabacc . Raynor , who believed that Calrissian had cheated him , hired Bossk to take his revenge on the gambler . Knowing that a direct assault would be pointless , the bounty hunter prepared a trap for the new Administrator . Bossk led a mercenary group to the lower levels of the city and sabotaged some equipment on a maintenance level to draw down Calrissian . Though the Baron Administrator was cautious enough to bring several troopers with him , he was trapped and cut off from communications when a blast door was shut behind him . Calrissian escaped through a nearby hangar , and the assassination attempt did not deter him from managing Cloud City . Prelude . In 1 ABY , Lando Calrissian , a professional gambler , played the card game sabacc in the Trest casino of Cloud City , a tibanna gas mining colony in the atmosphere of the gas giant Bespin . Calrissian ' s playing caught the attention of Baron Administrator Dominic Raynor , who invited Calrissian for a game in the Ecclessis Figg Room . They played a high - stakes game , and Calrissian lost all his cash and his private " Mu " - class shuttle , the " Cobra " . After the match , Lobot , the cyborg computer liaison officer of the city , revealed that the game had been rigged by the dealer . The match still counted as a loss for Calrissian , but he and Raynor played again , as Lobot gave the gambler a gift from workers of the city : a sum of five million credits . This time , however , Lobot , with the assistance of Raynor ' s consort Ymile , who hated living in the city , rigged the match in favor of Calrissian . The gambler risked all five million credits and his remaining starships against Raynor ' s two million credits and Cloud City , and Calrissian won . The former Baron Administrator was convinced that the scoundrel had cheated during the game and vowed to get his money back . Using his contacts , Raynor hired the Trandoshan bounty hunter Bossk to hunt down Calrissian and exact revenge . The ambush . Knowing that his target , the new Baron Administrator , would be well - protected , Bossk brought a band of mercenaries and cutthroats — a Twi ' lek scoundrel , another scoundrel of the same species , a Quarren assassin , and a Duros mercenary — to help him deal with any problems that might arise . After the group evaded Cloud City ' s security , Bossk sabotaged some vital equipment to set up the ambush in one of the city ' s maintenance decks . The Trandoshan was not sure of which turbolift Calrissian would arrive in , so he split his men up into every room near the lifts . Bossk ordered the others to take cover but remain in sight so they can lure Calrissian out . They intended to quickly kill any guards with the Administrator and capture Calrissian before he could find a way to escape . After the hunters took their position , Bossk hacked into the city ' s computer and , impersonating the chief engineer , he sent an urgent message to Calrissian . The Trandoshan claimed that a primary repulsorlift pod was about to break down , risking the entire city plunging through the clouds of Bespin . Calrissian responded to the call at once , bringing four Bespin Wing Guards and a female Twi ' lek bodyguard with him . After Calrissian and his guards entered the maintenance level , a blast door suddenly shut behind them . They found themselves trapped in a dark and steamy room and they immediately came under blasterfire from Bossk ' s bounty hunter group . The repulsorlift machinery ' s interference prevented Calrissian from calling for reinforcements through his wrist link ; and the maintenance deck ' s communication stations were not working , either , due to Bossk ' s sabotage . Knowing that another access port was nearby , Calrissian realized he had no choice but to fight and try to make his escape through the nearby hangar . Meanwhile , a quartet of loyal wing guards alerted by the sound of firefight were on their way to help the Baron Administrator . A member of Calrissian ' s party got to the nearby flight control center and sent out a distress call to the Security Headquarters . The arrive of the four additional wing guards helped Calrissian to escape through the nearby hangar bay . Aftermath . Since Bossk ' s ambush was unsuccessful , Raynor hired other beings to kill Calrissian , but the security of of the Baron Administrator was tightened with every attempt . After a Gank assassin also failed , Raynor sent a Human replica droid impersonating Queen Sarna of Drogheda , one of Calrissian ' s former lovers , to kill the gambler . The droid was led to the Administrator ' s personal office , but again , the assassination attempt failed . After that attempt , Calrissian got the idea of drawing out his opponent by playing dead . Calrissian assumed that , after the news of his " death " was spread , Raynor would come to Cloud City to buy the floating colony . Until then , Calrissian and Lobot traveled aboard the " Cobra " to the Yucrales sector in the Mid Rim to hide . There , however , they were ambushed by the female bounty hunter Thune and her modified YT - 1300 light freighter , the " Faceted " . They escaped to Quilken , and with the help of Mungo Baobab — heir of the Baobab Merchant Fleet — they captured Thune . Calrissian and Baobab used Thune as blackmail in order to capture Raynor , who was interrogated by Bwahl the Hutt until he dropped his vendetta . Behind the scenes . The ambush on Cloud City appeared in " Sore Loser ' s Revenge " , a Wizards . com online scenario for the " Star Wars Miniatures " collectible tabletop strategy game . The scenario was written by Eric Cagle for Wizards of the Coast and published online on October 8 , 2004 . The scenario suggested to play on the Tractor Beam Reactor Coupling map . Bossk captures Calrissian in an alternate ending to the scenario , but the short story " " has rendered this ending non - canon by featuring Calrissian unharmed a few days after Bossk ' s ambush .