His history lesson, however, came to an end when the Avengers burst in. They almost apprehended him, but he used a flash-bang to escape! With the heroes onto his previous operation, he switched it up and began traveling with a circus, as revealed in AVENGERS #223 when he fought Hawkeye and Scott Lang again.
Not everyone he's trained has been a villain, though. After getting nabbed by the feds in THING #32, he helped train the then-new Captain America, John Walker, beginning with CAPTAIN AMERICA #334. Red Skull later pulled some strings to help Taskmaster escape and then hired him to train-up the villain's crew.
He would return to his teaching role many times over the next several years, even working with Deadpool during the time when he lost his healing factor. He also appeared regularly in the pages of AGENT X, but took on a whole different level of job during CIVIL WAR when he became a member of the government-run Thunderbolts. During the final battle of that event, he attempted to kill Sue Storm, but her estranged husband took the bullet. And for those efforts, Taskmaster got smashed by the Invisible Woman's powers.
He popped in and out of prison soon afterwards, but wound up working for the government once again, this time as the trainer at Camp Hammond in AVENGERS: THE INITIATIVE. At the end of that series, he joined Norman Osborn's attack on Asgard as seen in SIEGE, though he initially refused. During the Heroic Age, TASKMASTER found its star on the run as every bad guy group around thought he'd been giving Steve Rogers information on their activities.