Leland Owlsley was a ruthless financier and associate of Wilson Fisk who played a part in Fisk's crusade to rebuild Hell's Kitchen, controlling Fisk's money flow and ensuring that his large profits were almost impossible to trace. He eventually lost faith in Fisk's leadership and attempted to assassinate Fisk's lover Vanessa Marianna in order to refocus him. When Fisk learned of his betrayal, he got revenge by killing him.
Criminal Money Man
Leland Owlsley spent his career ensuring that his rich partner's cash transactions became almost impossible to track, thereby hiding any illegal action they might be involved with. As this line of work often involved criminal activity, Owlsley made sure to keep a portion of the money for himself and his son in case they ever needed to go on the run from one of his partners.
Working with Wilson Fisk
Complications in New York
Owlsley was recruited by Wilson Fisk to control his money inputs and outputs, ensuring the authorities could not uncover their work. Owlsley took great pride in his work, having years of experience working for high-ranking criminal organizations and keeping their investments safe and secure. Although he had great respect for Fisk, Owlsley never fully trusted him and ensured he had backup plans ready in case Fisk ever betrayed him.
One night, Owlsley waited on the top of a building, along with Madame Gao, Nobu Yoshioka, Anatoly Ranskahov, and Vladimir Ranskahov, awaiting the arrival of Fisk. Owlsley spent much of the time complaining about the cold weather and Gao's and Yoshioka's refusal to speak English. Eventually, James Wesley arrived, claiming Fisk was too busy to attend. Wesley began to question why the Ranskahov's supply was down, to which they claimed their shipment had been attacked by a masked vigilante. Owlsley remained unphased by the news, claiming that new heroes in the city meant more career opportunities for them in the aftermath.
A few days later, Owlsley met with James Wesley to discuss the recent trial of John Healy. Owlsley could not understand why Wesley had chosen to hire Nelson and Murdock rather than using his own lawyers; Wesley explained that the two lawyers were clean, unlike Owlsley's lawyers. Owlsley continued asking questions, wanting to know why Fisk did not just have Healy killed like all their other problems. When Owlsley wondered why Wilson Fisk was not there to explain this himself, Wesley told him Fisk was busy looking at art, which greatly annoyed Owlsley.
War with the Russians
Owlsley was later called for another meeting, this time without the Ranskahov brothers. He observed pints of blood being washed off Fisk's car; when he asked if anyone else was concerned about the site, all he received was a laugh from Madame Gao. They were interrupted by the arrival of Wesley and Wilson Fisk. When Owlsley asked where the Ranskahov's were, Fisk announced that the Russian Mafia were no longer a part of their organization since Fisk had removed Anatoly Ranskahov's head with his car door the night before.
Both Gao and Nobu Yoshioka made it clear they were unhappy to have not been consulted in the matter; Owlsley also agreed. Fisk told Gao to continue moving her heroin to the Russians as usual until such a time that Fisk to take over the responsibility. Owlsley pointed out that the Russians' share of the money would likely go to Fisk, but Fisk promised all profits would be divided up equally between them. The group agreed on the proposal, with Owlsley noting he would not be foolish enough to go against them. Before they all departed, Owlsley nervously told them he would be collecting his stun gun.
Face to Face with the Masked Man
Owlsley met with Nobu Yoshioka in a car park to discuss the transport of his cargo, Owlsley made it clear that he knew what was being transported as he had decrypted the paperwork, he suggested that he and Yoshioka work to protect each other in light of what had recently happened with the Russian Mafia. Yoshioka instead told him that all men must stand alone or fall, he then left leaving Owlsley confused by what he meant. Once Yoshioka had gone Owlsley made his way to his car alone.
Before he could get away, he was confronted by the man in the mask who pinned him against his car and demanded to know who he worked for, promising that if Owlsley lied, he would hit in the face. When Owlsley tried to insist he worked for Silver & Brent, the man hit him hard in the face, causing his face to badly bruise. The man revealed he knew Owlsley worked for Wilson Fisk, but before he could learn anymore about Fisk's activities, he appeared distracted by a sound in the distance, Owlsley took the chance and hit him in the neck with a taser, stunning his attacker who fell to the floor before getting in his car and escaping.
Due to his recent attack by the masked man, Owlsley was taken to Wilson Fisk's armorer and tailor, Melvin Potter, who fitted him with a kevlar suit for protection. Owlsley and Fisk discussed what measures should be put in place to protect him, Fisk suggested that he should be taken to a safe house with armed guards while Owlsley complained bitterly that the recent attacks against them were forcing him to cancel plans to see his son who had planned to come to New York City to visit him.
Owlsley reminded Fisk that if the masked man was to throw him off a roof, then a lot of money would be lost along with him. When Fisk asked if this was a threat, Owlsley assured him that he was just stating the obvious. James Wesley then arrived and informed them that although Detective Christian Blake had been successfully assassinated by his former partner Carl Hoffman, the man in the mask had gotten into the hospital and got information out of him. Owlsley mocked Fisk for the failure, claiming that situations were becoming more complicated each day.
In an attempt to counteract the condemning exposure Fisk was likely to get as the masked man got closer to learning his identity and his plans, Fisk arranged a press conference with WHiH World News where he revealed himself to be a private donator of funds to rebuild Hell's Kitchen since the Battle of New York, before Ben Urich could expose him. During his speech, Owlsley stood beside Wesley and Vanessa Marianna, with Fisk using his friend Owlsley as an example when he condemned the actions of vigilantes like the masked man, calling Owlsley a pillar of the community.
Poisoning Vanessa Marianna
At Wilson Fisk's Penthouse, Owlsley was informed of Nobu Yoshioka's violent death while the pair prepared for a fundraiser. Owlsley was mortified by the news, despite Fisk and James Wesley's calm reactions. Fisk ordered Owlsley speak to Madame Gao and convince her that everything was fine in their organization. When Owlsley made a comment about Fisk's relationship with Vanessa Marianna, Fisk spoke to him about what it meant to be in love, seeing the change in Fisk caused by Marianna, Owlsley agreed to speak to Gao.
Owlsley had a meeting with Madame Gao where they agreed that Vanessa Marianna was having a negative effect on Wilson Fisk's work and they arranged for her to be poisoned at the fundraiser. After Fisk gave his speech, he spoke to Owlsley who assured him that the meeting was a success, Owlsley then offered each of them a glass of poisoned champagne which Marianna gratefully accepted. While Fisk was speaking to a senator, Marianna collapsed along with many other attendants who had also drunk the champagne. Fisk ran to her aid and Owlsley dropped his own glass having not taken a sip yet.
Vanessa Marianna was rushed to Metro-General Hospital and Owlsley went along with her and the rest of the group, asking the doctor if he also needed to be checked out as he was holding a glass of poisoned champagne; the nurse ignored him, however, and continued to focus her attention on Marianna. Owlsley watched as Wilson Fisk attempted to go with her surgery, but was stopped by the nurse.
While Marianna was being treated in the hospital, Owlsley spoke to James Wesley about how Fisk could run the business in his emotional condition. He claimed that whoever poisoned Marianna was likely after Fisk, not her, so they were in danger and needed proper leadership. When Wesley considered Madame Gao as a suspect, Owlsley claimed it was more likely the Hand who were responsible. They were then informed that Marianna was still alive, but three others who drank the champagne were now dead. Wesley then sent Owlsley to speak to Gao for support.
Owlsley later returned to the hospital and asked about Marianna's condition; Fisk, however, refused to speak to him and returned to her room. Owlsley spoke instead to James Wesley and claimed Gao had only spoken Chinese and quoted a fortune cookie, but she said she would stand with Fisk. Owlsley recommended that Fisk get back to work, but Wesley told him he would when he was ready, much to Owlsley's annoyance. Owlsley warned that whoever had gone after Fisk would come after him again and would likely succeed in killing him. Wesley simply told him to go home and get some rest.
Keeping the Business Running
- "Whatever war you're thinking about starting, don't lose sight of the endgame. Once Senator Cherryh has cleared the last of the zoning issues, you can tear down the rest of Hell's Kitchen and build your better tomorrow. It's a shame not everyone will be there to see it, but shit happens."
- ―Leland Owlsley to Wilson Fisk[src]
Owlsley was summoned by Wilson Fisk to a warehouse. When he arrived, he found Fisk staring at the corpse of James Wesley who had been shot in the chest. When he asked what had happened, Francis revealed that Wesley had received a call the night before and had gone out alone with a gun. Hearing this threw Fisk into a rage and he mercilessly beat Francis until Owlsley convinced him to stop. Owlsley discussed who could be responsible, explaining that Nobu Yoshioka's accounts were still active and his clan were the prime suspects after Yoshioka's death.
Owlsley had a meeting with Fisk that night where he claimed to have not found any information to blame the Hand although he still remained suspicious. The desperate Fisk then ordered Francis to double the reward for information until someone talked. Owlsley questioned if Francis could be trusted after the beating, but Fisk assured him that he could as Wesley had trusted him. Fisk then received a call on James Wesley's phone and immediately left the meeting, leaving Owsley both annoyed and concerned over Fisk's mental state due to Wesley's sudden murder.
Owlsley called a meeting with Madame Gao, who arrived late. She spoke English to him for the first time and claimed to have been detained by unfortunate events involving the man in the mask, who had raided and burned down her heroin warehouse. They discussed the risks of Wilson Fisk learning that they planned to assassinate Vanessa Marianna. He asked if she was responsible for James Wesley's death but she assured him she was not. She told him she was going to her homeland, which was much further away than China, and they would not speak again.
After being called for a meeting with Wilson Fisk to discuss the final stages of his plans for New York City, Owlsley explained that all was in place except for a replacement for Madame Gao's heroin trade. Fisk asked about some irregularities in the transactions. Owlsley claimed it was all perfectly normal as money was being moved around all the time. When he tried to hand the paperwork back, Fisk noted that his hands were shaking and he was shedding sweat. Seeing no other alternative, Owlsley confessed that he and Gao had tried to kill Vanessa Marianna although he denied any involvement with James Wesley's death.
Owlsley calmly informed Fisk that their partnership was at an end and Fisk was to hand over half his assets to him. When Fisk asked why he should do this, Owlsley informed him that he had Carl Hoffman and Hoffman was willing to go to the police if anything happened to him. This threw Fisk into a rage and he refused the offer and hit Owlsley hard across the face. Owlsley attempted to defend himself by striking Fisk on the neck with his taser, but Fisk was so angry it seemed to only fuel his rage. Fisk threw Owlsley down an elevator shaft to his death, where he split his skull upon impact.
- "Still got eight minutes. Owlsley don't call by then, we can get out of this dump."
- ―Owlsley's Henchman[src]
Once Owlsley was dead, Wilson Fisk ordered his contacts within the New York City Police Department to search through New York City and find where Owlsley hid Carl Hoffman. Meanwhile, Owlsley's men noticed he did not check in for 24 hours and prepared to move Hoffman from the hideout and turn him in to the FBI. However, Corbin and his officers raided the hideout and gunned down all of Owlsley's men, but before they could kill Hoffman, he was rescued by the masked vigilante. The vigilante had Hoffman to turn himself in to Brett Mahoney, as Nelson and Murdock organized his testimony, which allowed the FBI and the NYPD to disrupt Fisk's criminal network.
Leland Owlsley can be best summed up as a sardonic pragmatist. Leland often looked at situations from a realistic point of view. While not overly paranoid, Owlsley was pathologically skeptical and weary of both enemies and allies. When Kingpin grew increasingly attached to Vanessa Marianna, Owlsley became concerned about Fisk's ability to operate efficiently. Owlsley was vocal of his opinions, both when necessary to a situation and when it breached social etiquette. On one hand, Owlsley voiced his concern about Fisk's love life interfering with business to James Wesley, but on the other, he vocally made the blatant assumption that Nobu Yoshioka could translate Madame Gao's Chinese based on his being Asian. In contrast, Owlsley also knew when not to share his opinions. Owlsley knew what words upset the likes of Wilson Fisk and he knew not to say them. When he told Fisk that his death would result in a loss of a large amount of money, Fisk was not amused; thus Owlsley backpedaled by assuring it was only a hypothetical.
Oftentimes, Owlsley would follow any statement of concern with wit. Owlsley often found this humor in responding to another's statement, action, or situation in a very dry, realist-pessimistic tone. Owlsley's confidence lent itself to talking others down. He was not full of himself, but was secure in his actions more so than others are of their own. By betraying Fisk and his repeated comments of distrust in other allies, Owlsley showed loyalty only to himself. However, Owlsley has shown to have principle. Rather than seizing all of Fisk's finances, he only took half.
Owlsley further used his calm demeanor to appropriately respond to a situation. When jumped by Daredevil in a parking garage, he calmly attempted to reason until the vigilante was distracted, at which point he tased Daredevil and fled. Owlsley later used his taser in self defense against Wilson Fisk after his attempts to negotiate failed, albeit to no success. Owlsley's pragmatism and calm head have led him to success, in and beyond the finance world. Such success comes from Owlsley's planning. Prominent instances being his plan to poison Mariana and keeping Carl Hoffman alive and hidden from Fisk, both of which succeeded to further his agenda.
- Master Businessman: Owlsley was in charge of finances for Wilson Fisk's operation and was highly revered and successful businessman at Wall Street.
- Taser: Owlsley used a taser he carried around on Daredevil and then Wilson Fisk, only for the latter to fight its effects and become enraged.
- Armored Suit: Melvin Potter provided Owlsley with a protective suit.
|Appearances for Leland Owlsley|
- In the comics, Leland Owlsley was a silver-age Daredevil super-villain known as The Owl. Here, Owlsley was originally a crooked investor who used his resources to become a gangster that fought Daredevil and purchase an experimental super-serum which gave him the power to glide and fly through the air like a bird. However, the more Owlsley continued to operate as the Owl, the more his physical-appearance and brain became animalistic like one. This original version of Leland is referenced in the scene where he is getting a green suit tailored for him by Melvin Potter, with the unfinished suit resembling the green cloak that Leland often wore in the comics.
- Steven S. DeKnight confirmed Owlsley is dead, so his son Lee could become the Owl.
- Owlsley's plot to murder Vanessa Marianna is based on the plot the Kingpin's associate Lynch used in the comics, where, it was believed that Marianna's presence was only distracting Fisk from his criminal activities.
- Owlsley was a 46" long.
Behind the Scenes
- In an early draft of the episode Daredevil, Leland Owlsley was supposed to escape from New York City, only to get surprisingly killed by the Punisher in a post-credits scene, only showing the iconic skull insignia of the character and not his face. However, the plan was ultimately scrapped.
- Owlsley was originally portrayed by Peter Gerety, but after the actor injured his knee, Gunton was cast to replace him. Gerety's character was then renamed to Sammy Silke.
- David Shumbris was a stunt double for Bob Gunton in the role of Leland Owlsley.
- Daredevil: 1.12: The Ones We Leave Behind
- Daredevil: 1.08: Shadows in the Glass
- Daredevil: 1.13: Daredevil
- Daredevil: 1.01: Into the Ring
- Daredevil: 1.03: Rabbit in a Snowstorm
- Daredevil: 1.05: World on Fire
- Daredevil: 1.07: Stick
- Daredevil: 1.10: Nelson v. Murdock
- Daredevil: 1.11: The Path of the Righteous
- Marvel's Daredevil: Season 1 Spoiler Conversation with Showrunner Steven S. DeKnight
- Daredevil season 1 coda almost introduced Punisher, says showrunner
- A Conversation with Daredevil Showrunners Erik Oleson and Steven DeKnight