BIOGRAPHY
Not much is known about the unvarnished, true history of Anthony “Tony” Masters. His regular accent and personal anecdotes indicate he comes from the Bronx, New York, but other information suggests this could be a cover story or false memories. More than fifteen years ago, Masters was a decorated agent of S.H.I.E.L.D., working under Nick Fury. His dedication (some might say obsession) with being the best of the best was his defining trait. Tony met his wife, Mercedes Merced, as trainees in S.H.I.E.L.D. and they served on the same strike force.
On one mission, Tony and Mercedes’ unit uncovered the Nazi war criminal Dr. Horst Gorscht and his Odessa group, living in an isolated mountain village in the Andes, Bolivia. Gorscht was the scientist responsible for reverse-engineering the Super-Soldier process for Nazi agents, like Master Man and Warrior Woman, and he had devised a new means of indoctrinating subjects to 
their propaganda. His mnemonic primer serum would ready the human mind for an infusion of guiding thoughts and ideals from the cloned brain of Hitler himself. Tony destroyed Gorscht’s laboratory and fatally wounded the scientist, but the primer serum was too much of an opportunity to pass up. After hearing how the serum would “prime” his mind to absorb any new information at an accelerated rate, Tony Masters injected himself with the sole remaining sample of the serum.
Tony and Mercedes ended up as the only survivors of their strike team. Tony’s mind became a sponge for information, accumulating a wealth of knowledge on fighting styles, languages, tactical data, mission details and more. He developed photographic reflexes, the power to duplicate any action he observed another person perform. However, it came at a cost – this new information was overwriting the mnemonic pathways to his own long-term memories. The more he studied, the more he forgot who he was. This was tragic for Tony and Mercedes, as not only was he forgetting his wife, but her earliest memory was of being left behind by her parents. Through his own actions, Tony realized he was “abandoning” her as well. The emotional impact of this would linger in his subconscious long after he forgot what this primal feeling of guilt stemmed from.
Tony and Mercedes officially left S.H.I.E.L.D. behind and became a rogue operation, although Mercedes kept in touch with Nick Fury through backdoor channels. They salvaged the Odessa group’s resources and set up an isolated safe house in Tierra del Fuego as “The Org.” As his 
mind deteriorated, Tony and Mercedes crafted a “memory palace” for him, a series of triggers tied to sense memory that interacted with his new abilities. These triggers kept him linked to the Org, even through his progressive amnesia. Tony instinctively knew he was an Org operative and he implicitly trusted the Hub, Mercedes’ cover identity as his contact at the Org. The Hub became Tony’s surrogate memory, feeding him missions and intelligence reports as necessary to keep him on task.
The Org’s mission statement ended up being defined by a wrinkle in Tony’s memory problems. He soon forgot about S.H.I.E.L.D., the serum, Mercedes and the rest of his history, but he retained that primal guilt over abandoning her. This left him subconsciously convinced he was a “bad guy,” inclined towards villainy and black ops wetwork. Mercedes tried to sway him otherwise but, every time his memory faded, he reverted to this mindset. To capitalize on this tragedy, Mercedes leaned into the situation and set up the Org as a villainous infrastructure, the connective tissue of 
the underworld that shared intelligence, troops and other details between larger, unconnected groups like A.I.M., Hydra, the Secret Empire and more. Tony therefore performed mercenary work throughout the underworld, gathering information on the criminals with whom he interacted and passing it back to the Org. Mercedes then shared this actionable intelligence with Nick Fury through back channels, hoping he could use it for S.H.I.E.L.D. [Taskmaster (2nd series) #2-4]
Tony’s earliest mission for the Org was down in the Michoacan region of Mexico. He made contact with a group of federal agents trying to manage the drug trade and trained them to infiltrate and replace the drug runners themselves. Another ex-S.H.I.E.L.D. agent even assumed the identity of Don de la Muerte, masked enforcer for the new cartel. Tony was also inspired by the statue of 
Santa Muerte, Lady of the Shadows found in the Meso-American ruins they used as a training ground. He adopted her image as a death mask of his own, showing solidarity with the cartel as he trained them. Tony retained the masked look and, from that point on, Tony Masters disappeared completely beneath the cover identity of “Taskmaster.” [Taskmaster (2nd series) #2]
[Note: Before the second Taskmaster limited, he told several accounts about how he was “born” with his photographic reflexes, twirling lariats after watching the cowboys do it on TV. One anecdote had him claim he developed a lifelong fear of drowning after mimicking an Olympic dive before learning how to swim. Some sources even suggested this made him a mutant. After the retcon, these stories were apparently just that, a cover for his Swiss-cheesed memory.]
The Org’s goals and Taskmaster’s unique skill set led him to assume a particular niche in the underworld. Although he was a talented mercenary, he had unprecedented expertise as a training instructor. Taskmaster not only learned any fighting style he observed, he was equally talented at reverse engineering the style down to its individual components, and teaching those moves to others. Therefore, he opened an academy designed to teach basic competence in a variety of fighting skills to thugs off the street. Graduates of Taskmaster’s academy (and eventually academies) would go on to serve as henchmen to various criminal masterminds or terrorist organizations. The Org served as a “job matching” program for the academy, cementing itself as a vital part of the criminal underworld while also gathering intelligence through these contacts to funnel back to S.H.I.E.L.D.
With the growing number of super-heroes in the world, Taskmaster made a particular study of these crime-fighters in order to instruct his students on how to deal with them. He acquired video footage of many super-heroes in action, studying their moves and learning to duplicate them when possible. Taskmaster mastered the fighting styles of Daredevil, Iron Fist, Shang-Chi, even some of Spider-Man’s easier moves, and had replicas created of various weapons which he could wield with the skill of Captain America, Hawkeye, Black Knight and more. Although he could only duplicate humanly possible physical moves, Taskmaster could anticipate heroes like Ant-Man or Iron Man by studying patterns in their fighting style as well.
Taskmaster’s academy produced a number of “illustrious” graduates. Taskmaster trained the street tough named Brock Rumlow, who would go on to be the Red Skull’s top enforcer, Crossbones. [Captain America & Crossbones #1] Rumlow and Blanche Sitzinski, the future 
Anaconda of the Serpent Society, were instructors at the academy when Rachel Leighton trained under Taskmaster (before joining the Serpent Society herself as Diamondback). [Captain America (1st series) #403] Taskmaster was also hired by Hydra to train Jessica Drew before she became Agent Arachne, or Spider-Woman. [Spider-Woman: Origin #2-3]
[Note: The exact name of Taskmaster’s school is inconsistent. Deadpool (2nd series) consistently called it a Crime College, while Captain America (1st series) #403 gave it the lengthy title of Taskmaster’s Academy of Criminal Arts and Sciences. For convenience, we’ll just refer to it as the general name of Taskmaster’s Academy.]
Taskmaster was still forced to take mercenary jobs at times in order to make ends meet. He once took down a militia with Tyrell Farsa and the Black Swan. [Deadpool (2nd series) #68] He also contracted through the Assassins Guild – along with Bullseye, Sabretooth and Scalphunter – to hunt Cape Crow [Elektra (4th series) #1], and he accepted an offer by the Wingless Wizard to join a brand new Frightful Four. The Wizard was a self-important boss, however, who put his new 
teammates in training costumes until they proved themselves worthy of the illustrious history of the Frightful Four. Taskmaster was joined by Constrictor and Wade Wilson, fresh out of the Weapon X Program. They attempted to infiltrate the Baxter Building and kidnap Franklin Richards, but their plan was foiled by the Thing and the all-new, all-different Frightful Four went their separate ways. [Deadpool (2nd series) #35]