After Fisk started dating Vanessa Marianna, Owlsley and Madame Gao feared of Fisk wouldn't remain unaffected by emotions. The two allied and deviced a plan to try to kill Vanessa as they poisoned some of the drinks at a charity party Fisk was attending to.
After Madame Gao had left New York, Leland confronted Fisk, who had already discovered some irregularities in his records. Owlsley admitted the blame for stealing money from Fisk as well as trying to kill Vanessa, but he revealed a piece of information to prevent Fisk from killing him. Owlsley had kept Carl Hoffman, a dirty cop who could blow Fisk's operations wide open, in hiding as a leverage. Despite this, Fisk killed Leland out of rage.
- Bob Gunton portrayed Lesland Owlsley as a main character in the first season of the online series Marvel's Daredevil.
- In the original plans for the first season of Marvel's Daredevil, Owlsley was going to live until the post-credit scene of the season finale. The scene would've featured Owlsley heading to a boat, but he would've come across a mysterious man that would've shot him. After Owlsley's death, the camera would've panned up to the chest of Owlsley's assailant, showing a skull painted in the body armor, teasing the Punisher, a character that debuted in the second season of the show.
- 9 Appearances of Leland Owlsley (Earth-199999)
- Minor Appearances of Leland Owlsley (Earth-199999)
- Media Leland Owlsley (Earth-199999) was Mentioned in
- 4 Images featuring Leland Owlsley (Earth-199999)
- Quotations by or about Leland Owlsley (Earth-199999)
- Character Gallery: Leland Owlsley (Earth-199999)
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