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Taskmaster is Olga Kurylenko's character Anya Dreykov, the daughter of Ray Winstone's character Viktor Dreykov, the director of the Red Room. She was Natasha's best friend, but when Natasha decided to escape, Anya tried to stop her and they fought. Natasha was forced to choose between leaving Anya to die in an explosion and escape, or rescue her and risk being recaptured. She chose to escape, something that has always haunted her.

Anya was severely injured but survived and was rebuilt by Dreykov and Rachel Weisz's character Melina Vostokoff with cybernetic enhancements, including to analyze and mimic other people's fighting skills. Anya lives under Dreykov's control and is ordered by Dreykov to recapture Natasha. In the end, Natasha is once again forced to choose between leaving Anya to die to escape or helping her and risk capture. This time, she chooses Anya, who forgives Natasha and dies in her arms from the injuries she suffered in the final battle.

O.T. Fagbenle's character Rick Mason is a red herring in regards to being Taskmaster, but he is secretly working for Dreykov and wants revenge against Natasha for ruining his life by leaking S.H.I.E.L.D.'s secrets online, exposing his identity and forcing him to live underground. Also, the movie ends with Ross retrieving the specs for Taskmaster's implants and planning to create his own version.