Brown (later gray)
|Chronological and political information|
- "You're a crusader, my dear princess, I'm not. You have your games to play, I have mine."
- ―Simon Greyshade
During the waning days of the Galactic Republic, Greyshade was considered one of the most corrupt members of the Galactic Senate, and he enjoyed every minute of his term and the perks of holding the office. When not in the Senate, he would drive across the skies of Coruscant in his yellow XJ-6 airspeeder, spend time with various female companions, or engage in gambling with fellow senators (he even introduced legislation to legalize gambling in the entire Republic). After fellow Senator Padmé Amidala's assassination attempt, Anakin Skywalker "borrowed" the airspeeder to pursue bounty hunter Zam Wesell.
During the Clone Wars, he would remain as one of the few neutral senators in the Senate. He resigned shortly after the formation of the Galactic Empire and took over the administration of a gambling resort known as The Wheel. Prior to his resignation, he was part of the committee that expelled Mako Spince from the Imperial Academy.
The Wheel instantly made Greyshade a very wealthy man, mostly due to its exemption from any Imperial law or interference, which Greyshade had acquired by making a "generous" offer that the bulk of The Wheel’s tax profits would pay for the Empire’s military funding.
During the Galactic Civil War, the Millennium Falcon was pursued by the relentless Imperial Commander Strom, to The Wheel. Much to Greyshade's displeasure Strom ordered Imperial stormtroopers onto the gambling station to search for the Falcon's fugitive crew. He claimed that they had attacked a House of Tagge merchant ship which was transporting profits from The Wheel. Greyshade relented but allowed an Imperial presence only on the lower levels, keeping the distraction away from the paying customers on the upper levels.
As Greyshade's security cameras tracked the fugitives on board, he discovered the identity of one of the Falcon's passengers was Leia Organa, an old colleague from the Imperial Senate, and an unrequited love of his. He sent his Wheel Security Force to free her from the stormtroopers and bring her to his suite where Leia revealed to Greyshade that it was actually an Imperial attack made to look like the Rebels that had hijacked The Wheel's profits.
Strom arrived at Greyshade's suite. The two men had always hated each other and Strom announced that the fact that Greyshade was harboring an enemy of the state was grounds enough to kill him. But, before he could carry out his threat, he was disarmed by Master-Com, the main computer running the Wheel.
Greyshade then arranged a deal with Strom where he would not reveal the truth behind the attack of the merchant ship and ensure that all the Rebels would be killed on The Wheel. In exchange Leia Organa would be allowed to remain there with him.
And so Greyshade set up events so that Han Solo and Chewbacca would face each other in The Big Game, and that the hospitalized Luke Skywalker would not recover from his coma-like state. The droids C-3PO and R2-D2 were also taken by The Wheel and scheduled to have their memories flushed when Master-Com released them because he was curious about their relationship with their master, Luke Skywalker.
But all did not go according to plan as Leia escaped from Greyshade's suite, and reunited with Luke who had now recovered from his sickness and escaped from the medical center. In the meantime, Greyshade had double-crossed his Imperial partner by sending his Wheel Security Force aboard Strom's Pursuit-class light cruiser to retrieve the stolen Wheel profits and load them onto his own personal space yacht. He then drugged the Imperial Commander and planned to make a clean escape with the treasure when he caught Leia and Luke along the way. He proposed to Leia that he would allow all of her friends to go free if she would consent to leave with him in his yacht. At that point it appeared that Han Solo had just been killed in The Big Game, and a distraught Leia accepted his offer.
Strom recovered and ordered his stormtroopers to kill the Rebels and his traitorous partner, and they soon had the fugitives pinned down. Luke volunteered to stay behind to cover their escape, but Greyshade was tired of being upstaged by Luke's bravery and had also gained a newfound affection for his droid Master-Com. He decided that he would stay behind and let the Rebels escape in his yacht, which they did, but he was injured in the standoff with the stormtroopers. Strom finally caught up with the wounded Greyshade and intended to murder the traitor, but Greyshade tossed a proton grenade in the Commander's direction killing him. However, both Greyshade and Master-Com were caught in the blast and fatally wounded as a result.
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