An 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.
Calrissian reveals his cards to Raynor.
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.
Bossk set up an ambush for Calrissian.
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.
The security of the Baron Administrator was strengthened after the assassination attempts.
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.
A possible place of the ambush
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 Lando Calrissian: Idiot's Array has rendered this ending non-canon by featuring Calrissian unharmed a few days after Bossk's ambush.