Sgt. Simian

Before the First Robotnik War, Simon Simian lived in the Mobian Jungle with his grandfather among a colony of peaceful apes. When Dr. Robotnik's forces first began to spread out, his grandfather was shot at by robots and Simon demanded they go to war. The colony decided against it due to their peaceful ways, and Simon ran away to start his own war on Robotnik after he was discovered stockpiling weapons. However, during a lone assault on a base of Robotnik's, he became overwhelmed by SWATbots, facing certain death with no regrets. The next thing he knew, Simon woke up to discover that he was alive and unharmed, as Mammoth Mogul had rescued him. Simon's actions had impressed Mogul and he convinced the young ape to work for him with the promise of gaining power. He worked for Mammoth Mogul for a time and eventually returned home with permission, only to find colony had become militant and opposed Robotnik. Simon's grandfather admitted he had been right the whole time and asked him to become a sergeant and lead them in battle, but Simian just took the sergeant's sash, claiming they weren't worthy of him. He walked away from the colony, now known as Sergeant Simian.

Like the rest of the Fearsome Foursome-Lightning Lynx, Predator Hawk, and Flying Frog - Sergeant Simian debuted as an agent of Mammoth Mogul's, attacking the Chaotix on his orders. After being defeated and retreating from this battle, he would return to help Mogul in his bid to claim the Sword of Acorns by pitting the Chaotix and Freedom Fighters against each other. Simian's purpose involved serving as the substance behind Mogul's illusions of Mighty the Armadillo and Bunnie Rabbot, which initially had the two groups fighting. When the more level-headed members of each team noticed the errors in these illusions, however, the scheme was blown and Simian was captured along with his teammates.

Along with the rest of the Fearsome Foursome, Sergeant Simian would be sent to Devil's Gulag and imprisoned for some time. However, due to the actions of an as yet concealed Dr. Eggman, the teammates were able to escape along with fellow criminals Snively Kintobor, Nack the Weasel, Sleuth Dog, Drago Wolf, Warlord Kodos, and Uma Arachnis. Joining the assemblage of villains under Snively's leadership, Simian confronted the Freedom Fighters again in capturing Nate Morgan, a venture that proved much more successful than his previous encounters with the heroes. Sadly, his success was short-lived, as he and the rest of the future Destructix were defeated and captured by the Royal Secret Service under Geoffrey St. John.

Following another escape from Devil's Gulag, Sergeant Simian and his teammates - which now included Sleuth and Drago - would take up residence in a factory that had once belonged to Dr. Ivo Robotnik, keeping Tommy Turtle as a convenient punching bag. Later, Sonic the Hedgehog infiltrated this factory to liberate his old friend Tommy, only to watch as the Destructix - though they were not yet called that-attempted to make a deal with Dr. Eggman to sell him the factory, which by rights he already owned. Simian and the others were then subjected to Roboticization, becoming Robians in service to Eggman. Due to Sleuth's apparently suicidal attempt to prevent his own transformation, it seemed briefly as though the Destructix had been destroyed, but they in fact survived and were De-Roboticized by the Bem. Later, robotic doubles of their Robian forms would attack Sonic as part of a ruse to get an Auto Automaton of Tommy Turtle into Knothole. When recovered by Eggman, these doubles contained video of the Destructix making a deal with "Anonymous", a mysterious being who would later turn out to be Eggman's computer virus son A.D.A.M.

Once the Destructix were officially organized, all of its members set out to recapture Mammoth Mogul's Chaos Emerald in order to release him. Sergeant Simian engaged the Freedom Fighters and Chaotix yet again, but as usual was outclassed and outnumbered and so defeated. He and the others were taken to prison, only to be liberated when Mogul escaped from the Emerald himself, renewing his pledge of loyalty to the Mammoth. When Ixis Naugus arrived and challenged Mogul for the Crown of Acorns, Simian fought against his Arachne as well as the arriving Freedom Fighters and Chaotix. When Mogul and Naugus joined forces, the battle continued between only two sides, but then ended with the destruction of the Sword and Crown of Acorns and the capture of the villains by the Egg Fleet. Lynx and his compatriots were then teleported to the Egg Grape Chamber, where Mogul briefly protected them before lowering his shields and leaving them at Eggman's mercy. Luckily for the criminals, Dr. Finitevus arrived shortly thereafter with Scourge the Hedgehog and Rouge the Bat to liberate the Destructix. The doctor called upon them for their muscle, first requiring Lynx and his teammates to play the part of reformed mercenaries by defending the helpless Echidnas of Angel Island from the Dingoes.

Sergeant and his compatriots revealed their true colors soon enough by ambushing and capturing Knuckles the Echidna when he returned to Angel Island and handing him over to the Dark Legion. Following his brainwashing and transformation into Enerjak, the Destructix - now joined by Fiona Fox in place of Rouge - were set at watch over a device created by the Brotherhood of Guardians to destroy Enerjak in the event of his return. They were soon challenged by Sonic, Julie-Su, and Locke as they attempted to claim the device, only to be thwarted by Archimedes the Fire Ant and then have their mission rendered unnecessary by Sonic's destruction of the weapon. Unnerved by the ensuing battle between Enerjak and Super Sonic, Sergeant Simian and his allies left through one of Finitevus' Warp Rings, having decided to become full-fledged mercenaries.

The group soon found themselves once again employed by Mammoth Mogul, who commissioned them to bring him Sonic's running shoes. After a brief fight with Sonic, Sally, and fellow mercenaries Bark the Polar Bear and Bean the Dynamite - whom Mogul had also hired but who had switched sides on Sally's offer of better payment - they captured Sonic and took him to Mogul's casino. They were all then defeated by Sonic, Sally, Amy Rose, and Geoffrey St. John, only for Rouge to pass the word to them that Mogul's plan all along had been to discredit Sonic by capturing him and then having him confront Mogul without evidence that Mogul had been involved.