Black Widow: Everything You Need To Know About Taskmaster
2. After He Became A Mercenary, He Still Worked For SHIELD
During the Civil War saga, Maria Hill replaced Nick Fury as the director of SHIELD. Hill is a big fan of the phrase, "choosing the lesser of two evils" since she has allied with supervillains many times when she believed it was for the greater good. SHIELD hired Taskmaster to be a member of the Thunderbolts; a group of prisoners who must perform suicide missions to reduce their sentence. (Before you ask, yes, it is a total rip-off of Suicide Squad.)
Not only that, Hill personally chose Taskmaster to test the security systems of the SHIELD's helicarriers. Since he is a world-class mercenary, spy, thief, and assassin, she thought he would be able to find weaknesses in her security that her staff would miss. For his service, he was given a full pardon for all previous transgressions. With his slate wiped clean, Taskmaster was no longer a criminal for the first time in years. This was his chance to start a new life.
Obviously, that never happened. (It would be a pretty boring comic, wouldn't it?) It didn't take long before he was back to training henchmen, taking mercenary jobs, and punching superheroes in the face.