Simon Escher
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Simon Escher (Garret Dillahunt) was the ace professional assassin/operative for Management prior to Michael Westen being "burned." He is responsible for numerous bombings, arsons, kidnappings and assassinations for the organization and apparently was high-ranking enough to gain access to the names and occupations of all members of Management. Sometime prior to Season 3, he went insane and began carrying out terrorist attacks for his own interests. According to "Vaughn", his handler, Simon became too high-risk for Management to continue doing business with and so they attempted to have him killed; an effort that failed, and led to Simon beginning his vendetta against Management.
He compiled a list of names, aliases, occupations and locations of all members of Management as an insurance policy. He used a book-code of the names in the Escher Family Bible, which can only be decrypted by a second portion of the code. Realizing he was too small a cog in the machine to strike at Management, he enlisted the help of a private-sector corporation called Drake Technologies, and its CEO, John Barrett, who he promised the list to in exchange for assisting him in taking Management out. Sometime after, however, he was captured by Management and taken into exile as a super-max prisoner. Management then turned their sights to another skilled and talented spy - Michael Westen - and had him burned and all of Simon's crimes pinned on him to secure his dismissal. Somehow this information was discovered by Simon, who became obsessed with/furious at Michael for taking the "credit for his work."
Barrett, desperate to the Management List, enlisted the services of a freelance spy-wrangler named Tom Strickler and his associates to have Simon broken out of a super-max prison so he could lead them to the Family Bible. He offered them $10-million dollars to intercept a flight meant to transport Simon out of the country. After Michael gunned down Strickler, a professional assassin, Mason Gilroy, took it upon himself to break Simon out for the price-tag promised to them, ultimately forcing Michael to assist him in the dangerous jail-break. Once the pilots of the plane were bribed by Gilroy to release Simon, he turned on Gilroy: shooting him in the abdomen and strapping him to an explosive device that blew him up inside of his car.
Now a free man and on the loose once again, Simon first turned his attention to Michael, who he needed to lure Management to him in Miami. After a game of cat-and-mouse between them, Michael ultimately contacted "The Old Man" - a high-ranking member of Management that Michael had alluded in the past - and asked for his help in capturing Simon again. Their meeting atop a helipad turned deadly, however, when Simon detonated a bomb that blew up the helicopter and then stormed the rooftop under the disguise of a police officer. He killed several bodyguards working for The Old Man until he was able to capture him and beat up Michael, with the latter barely escaping death by sliding down a construction chute. Simon restrained The Old Man inside the back of an ambulance that served as his escape vehicle and then fled the scene of the bombings. Michael hijacked another car and crashed it into the side of the ambulance as Simon was fleeing. A brief struggle between Simon and Michael ended with Simon facing the business end of his own Walther P99; promising Michael that he'd soon "end up just like [Simon]."
Once again a prisoner of Management, Simon resurfaced towards the middle of Season 4, when Michael requested he be returned to Miami for interrogation about who he was working for. Simon broke free of his restraints and attacked Michael, hurling them both out of a window and onto a deck. There, he told Michael of the location of a buried stash he had hidden inside a cemetery containing an audio-tape that implicated "Vaughn" in Michael's burn notice. He also led Michael and his allies to John Barrett.
