Vladimir was a young boy when he heard the legend of the Grim Hunter as told to him by his father's servant, Gregor. The fiercest hunters and warriors of all time feared his prowess according to Gregor. Trained by his father, Sergei, Vladimir learned how to hunt and fight in the same manner as his father. Years later, Vladimir learned of his father's death and blaming Spider-Man, sought revenge. Jason Macendale visited Vladimir at the Kravinoff estate in Russia seeking the power of Vlad's father in exchage for Kraven's journals. Though Vladimir and Gregor attempted to renege on the deal, Macendale fled the mansion, superhumanly enhanced by an experimental version of Kraven's elixir. Vladimir used the journal to perfect the elixir and enhanced his own physiology to superhuman levels. With his new found abilities, Vladimir decided to call himself the Grim Hunter after the legendary character. From the journal Vladimir read accounts of all of his father's battles with Spider-Man and memorized the descriptions of Spider-Man's moves and mannerisms.

In America, he tracked Spider-Man's scent and found him chasing two muggers. Vladimir killed the muggers with his bolos and proceeded to attack Spider-Man. A battle soon followed with the Grim Hunter initially winning. However, through determination, Spider-Man overcame the Hunter's attacks and soundly defeated him. Gregor tried to intervene by threatening to use his helicopter’s guns to open fire but Spider-Man pulled Gregor out of the helicopter and brought the two of them to jail.

The Grim Hunter bribed his way out of jail and tracked down Spider-Man's scent again. Unfortunately for him, the trail led him to Ben Reilly who, unbeknownst to the Hunter, was a clone of Peter Parker, the real Spider-Man. Ben Reilly managed to escape from the Grim Hunter but this only bought him some time. It was clear that Vladimir had become obsessed with destroying Spider-Man just as his father had. Still chasing Ben Reilly's scent, the Grim Hunter found him in a battle against Kaine. Thinking that Kaine was trying to interfere with his destiny, the Grim Hunter attacked. Despite Ben's efforts to stop him, Kaine easily overwhelmed Vladimir and branded him with "the mark of Kaine". On death's door he staggered to Gregor falling in his arms and died shortly after that.