At some point Timothy Karlskin joined Taskmaster's academy where he was trained to become a criminal version of Captain America while his team-mates Blood Spider and Jagged Bow were trained to be versions of Hawkeye and Spider-Man.
When the Red Skull hired Taskmaster to kill Spider-Man, who was searching for answers about his parents, Taskmaster viewed this as an opportunity to try out new recruits. However, Spider-Man and the anti-terrorist Solo, who was also searching for the Red Skull, defeated the trio.