Taskmaster's History
Early life
Tony Masters gained an ability known as "photographic reflexes" during a mission as a S.H.I.E.L.D. agent. This ability enabled him to watch another person's physical movements and duplicate them without any practice, no matter how complex. He was previously a naturally gifted athlete who trained himself to superb physical condition. His power was only limited by the fact that the memories he gained by watching others overwrote his personal memories. As a result, Tony forgot his wife and field agent partner, Mercedes Masters, as well as his own history with S.H.I.E.L.D. Mercedes crafted an elaborate set-up to help control and guide Tony in his new guise as Taskmaster. Using a series of muscle memory and reflexive tasks, she linked Taskmaster to "the Org", his "handler" between jobs and a constant to keep him on task despite his frequently over-written memory. The Org was actually Mercedes herself, gathering intelligence and feeding it back to S.H.I.E.L.D. thanks to Taskmaster's reports. Tony therefore became the ultimate double agent in the super-villain underground -- one who didn't even know what he was.
Taskmaster
Tony decided to use his stolen capital to establish a base of operations to train criminals known as the Taskmaster's Academy. He took the the name Taskmaster and began training anyone that could pay. When Dr. Pernell Solomon used the Solomon Institute for the Criminally Insane as a front, he used the Taskmasters school's resources to create a clone of himself called Selbe. When he required an organ donation due to possessing an extremely rare blood type, the clone, learning of his fate, contacted the Avengers. Taskmaster captured Yellowjacket, the Wasp, and Ant-Man when they attacked the site. Taskmaster battled the Avengers, who exposed his front operation. He was defeated and fled after a fight with the Avengers newest member the robot Jocasta, whose lack of body language made it impossible for Taskmaster to predict her next move.
In addition to his training academies, Taskmaster also lent himself out as a mercenary or private instructor. He trained John Walker to be the new Captain America for the Commission on Superhuman Activities, then trained Cutthroat to fight Captain America on behalf of the Red Skull.
New Taskmaster
Eventually, the Taskmaster considerably changed his appearance. He wore a costume apparently modeled after tactical body armor, replacing his previous pirate-themed garb. The Taskmaster also ceased carrying an arsenal of duplicate weapons. Taskmaster began operating as a more traditional mercenary instead of as an instructor. He first met Sandi Brandenberg after beginning this mercenary M.O.
Taskmaster vs Iron Man
Taskmaster spent some time around Wade Wilson after Deadpool became famous for the Four Winds hit and hired Sandi as his personal assistant. Wilson was not responsible for the hit, however, and the real assassin Black Swan came after him and his friends. Wilson and the Swan were seemingly killed in an explosion.
When Sandi found a stray amnesiac with super-healing powers, she brought him home because she thought he must be Mr. Wilson. Taskmaster reluctantly helped train "Alex Hayden" at Sandi's request, but thought such an inexperienced merc would just get her into more trouble. He tried to have Alex killed by setting him up on a job to steal the Punisher's .45s, and later reported to the surviving Four Winds that Hayden was Wilson. When Sandi was put in danger by this last act, though, Taskmaster chose to stand side-by-side with Hayden and his friend Outlaw against the Four Winds.
Alex and Sandi eventually slept together, which nearly drove Taskmaster nuts. Things got even more complicated when both Deadpool and Black Swan returned. In the end, Taskmaster and Sandi seemingly ended up together with Hayden and Outlaw reunited, and the entire group stayed together for a time as Agency X.
Taskmaster was eventually hired by the Committee to take out Moon Knight. He raided Spector's apartment, but was unable to kill him. Spector piloted his Mooncopter to the Committee's Manhattan headquarters and flew it directly into their office. Miraculously, all of the Committee members survived the attack.
He was briefly one of the Thunderbolts' detainees, later being released and assigned to Camp Hammond to serve as a trainer for the Initiative recruits while their former drill instructor, Gauntlet, recuperated from injuries sustained from one of his trainees. During this time, a formerly deceased Initiative member, Michael Van Patrick acquired a weapon called the Tactigon and began assaulting everyone at the camp. The Taskmaster had little interest in participating in the fight, preferring instead to sit by the sidelines with one of his charges, Ant-Man.
Taskmaster then took over training for the entire Initiative and participated in the siege of Asgard. He joined in the fight against Thor, since it would help him become a more reputable assassin. He fought both Captain Americas at the same time with unexpected success. Able to see that his side was not winning the fight, Taskmaster fled with the Constrictor to return to mercenary work. He taunted Norman Osborn with the knowledge that he had earlier assisted Deadpool.
After losing his weapons in Tokyo, Tony began a quest to attempt to remember some of the things he had been forgetting. On this quest, his former handler, The Org, seemed to put out a billion-dollar bounty on his head. Many of the teams he formerly trained, including A.I.M. and Hydra, attempted to collect the bounty by killing him, but only succeeded in tracking him on his quest. It was during this memory quest that Tony temporarily learned his true past, that of a married former S.H.I.E.L.D. agent who mistakenly took a Nazi serum that granted him his extraordinary abilities. He also briefly met his wife and handler, Mercedes Merced. Ultimately, he was forced to learn the new fighting skill of Redshirt, the man who put out the fake bounty, which erased all of his knowledge regarding his past. Apparently, this had happened repeatedly in the past.
Secret Avengers
Taskmaster was asked to become a member of S.H.I.E.L.D.'s Secret Avengers team after being rescued by Nick Fury Jr. from the criminal nation of Bagalia. His first mission was to join A.I.M.'s High Council as a double-agent, taking the role of Minister of Defense.
When he tried to free Mockingbird from A.I.M. captivity, he was attacked from behind by the TESS-One, and shot in the head by Mockingbird herself, who had been brainwashed by A.I.M. However, Mockingbird purposely missed any vitals and Taskmaster was revealed to be alive but left in a vegetative state. As they thought he was dead, the Secret Avengers left him behind, but his survival was discovered by Mentallo, who had developed a friendship with him. Mentallo kept his survival a secret and sought to cure him with with his nanobots.
After briefly becoming a part of Baron Zemo's Hydra, Taskmaster moved his base of operations to Bagalia, becoming the sheriff of the small country.
