Taskmaster then began a program of observing the fighting techniques of a large number of costumed heroes and villains (using archival television news broadcasts). He initially used his fighting skills to execute several successful grand larcenies, but he had not properly anticipated the dangers involved. He decided to use his stolen capital to establish a center for training aspiring criminals to become polished professionals. His goal was to become a supplier for criminal organizations around the world. Designing a costume, he took the name Taskmaster and began to train a large number of thugs at criminal academies he had located around the United States. However, his existence was eventually revealed when the head of one of these academies used the school's resources to create a clone of himself when he required an organ donation; learning of his fate, the clone managed to contact the Avengers, and Taskmaster was subsequently forced to flee after a confrontation with Jocasta, whose lack of body language made it impossible for Taskmaster to predict her next move.
Through Douglas Rockwell, the head of the President's Commission on Superhuman Activities, "Mr. Smith" (actually the Red Skull) arranged for Taskmaster to train John Walker (then known as Captain America, later known as U.S. Agent) in order to make him appear to be the real Captain America. In order to conceal the Red Skull's involvement, Douglas Rockwell had the Commission work out a deal to have years taken off Taskmaster's sentence in return for training Walker. After Taskmaster successfully trained Walker, the Red Skull arranged for him to escape from the Commission's detention center so he could continue training lackeys and the Red Skull himself.
On another occasion, Taskmaster was hired by the Triune Understanding- a religious group secretly masterminding a smear campaign to paint the Avengers as being religiously and racially intolerant- to stage an attack on a Triune facility. Posing as Captain America, he contacted Warbird, Ant-Man, Silverclaw and Captain Marvel, claiming that he needed their help to destroy a Triune building containing a mind-control machine. Although they saw through his deception and subsequently defeated him- thanks to Captain Marvel transforming into Rick Jones mere milliseconds away from Taskmaster, thus causing a complete change of attack before Taskmaster could react-, the building was destroyed in the ensuing battle and Taskmaster escaped, leaving the heroes lacking any evidence of their story.
Taskmaster continued to train numerous villains and thugs until the Avengers began to search out and shut down some of his academies across the United States. Taskmaster began to spend more time working as a mercenary in order to make up for the loss of profit. This led him to join Agency X at the behest of his love interest Sandi Brandenberg, in missions from time to time, while continuing to teach at his academies around the world. More recently, Taskmaster is once again seen as a hired mercenary, contracted by the Committee to kill Marc Spector, Moon Knight. Here, though clearly in Taskmaster costume, he is only so far referred to as "Contingency T" and "Tasky" when talking to himself. Taskmaster was misled with information that Moon Knight was broken, desiring death and friendless. During the conflict these factors all proved to be false as Marc's ex-girlfriend and his butler came to his defense and he found the will to fight back. Despite his superior fighting abilities, Taskmaster was defeated. Moon Knight then carved off the skin of Taskmaster's facemask, though left him alive.
In the final issue of Civil War, Taskmaster was among the Thunderbolts battling the secret Avengers in New York. He attempts to kill Susan Storm, only for Reed Richards to take the bullet. Enraged, Sue crushes him with an invisible telekinetic field, rendering him unconscious. He was sent to the Negative Zone Prison with the other 'Major-League' members of the Thunderbolt army such as Lady Deathstrike, but was apparently freed by Deadpool during the events of Cable and Deadpool #36. In order to regain his reputation as a mercenary, Deadpool frees Taskmaster from his imprisonment in order to have a showdown with him while potential merc contractors watched from their captive position in a nearby prison. Taskmaster is again referred to as "Tasky" by Deadpool, and a fight ensues between him and a manacled Deadpool. He mentions his professional ethics, but this simply comes down to deciding to simply maim his opponent rather than kill him. In the end, he is defeated by Deadpool, who, in spite of the victory, fails to impress his captive audience. After being thanked for letting him win, Taskmaster tells Deadpool that he had not let him win, "The truth is... You're that good. You've always been that good. Which won't get you a cup of coffee until you figure out how to be a professional..."
Taskmaster was given a full presidential pardon for his efforts in testing the security of the S.H.I.E.L.D. helicarrier, in which he was able to break in and place Deputy Director Maria Hill in his sights. Though he was allowed to leave, a threatening message left in Hill's private bathroom revealed that if he ever desired, S.H.I.E.L.D. is no difficult feat.
Taskmaster's power to duplicate the abilities of others is purely dependent on sight, and restricted to physical motions. For example, he could copy a virtuoso pianist's performance by watching him play, but would not gain the ability to read sheet music. As a child, he almost drowned when he perfectly duplicated another swimmer's dive, forgetting that he had not yet learned how to swim once he hit the water.
Once Taskmaster has assimilated another fighter's style, he is often able to predict his opponent's next move. However, this advantage can be negated by fighters who are unpredictable, such as Deadpool and Wolverine. In addition, Taskmaster has discovered that after watching martial arts movies on fast-forward he is able to briefly duplicate the moves at a greatly increased velocity, effectively giving him a limited form of superspeed. However, as he does not have any sort of enhanced endurance, this puts a great strain on his body and he is only able to fight in this manner for short periods of time.
Taskmaster has had his scientists duplicate versions of a variety of weapons used by Marvel characters, which he can use with nearly as great facility as their respective owners. In the past, he carried duplicates of Daredevil's billy club, Hawkeye's trick arrows and bow, and Captain America's shield. He also carried a sword (in emulation of the Black Knight), a lasso, and a Colt .45 semi-automatic pistol (in emulation of the Punisher). He has recently been seen throwing "crescent darts" during his bout with Moon Knight, in imitation of Moon Knight's fighting methods (However, Taskmaster has said he prefers not to use Moon Knight's style, since Moon Knight would rather take a punch than dodge it).
Taskmaster's character was considerably revised in a 2002 UDON-created miniseries, which itself led into repeated appearances in the UDON drawn series', Deadpool and Agent X. Most visibly, he wore a costume apparently modeled after tactical body armor, with the addition of a skull mask, replacing his pirate-themed garb. During this time, Taskmaster also ceased carrying an arsenal of duplicate weapons. Instead, his armament consisted primarily of a pair of semi-automatic handguns and a katana, which he wields with the fighting style of the Silver Samurai. He also carried a prototype wrist-mounted device, stolen from S.H.I.E.L.D., which can spontaneously create simple shapes out of solid energy, saving him the trouble of weighing himself down with many weapons. In particular, he was fond of using the device to create copies of Captain America's shield and Spider-Man's webbing. Taskmaster also used a holographic device to disguise his appearance and impersonate others. However, in his recent appearances in Moon Knight and Civil War, Taskmaster has returned to his old costume and weapons.
The Taskmaster's only "weakness" is a deep-set severe fear of drowning, based on the aforementioned childhood trauma.