Leland Owlsley

"I'm glad to hear there's some new blood running around out there. Heroes and their consequences are why we have our current opportunities."

- Leland Owlsley

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 catch by the FBI. 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 Owlsley.

Criminal Money Man
"I've spent my entire life hiding assets overseas from pricks like you."

- Leland Owlsley to Wilson Fisk

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.

Complications in New York
Owlsley was recruited by Wilson Fisk to control Fisk's 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 organisations and keeping their investments safe and secure. Although he had great respect for Fisk, Owlsley never fully trusted him and ensured he had back up 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 Wilson 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; they claimed their shipment had been attacked by a masked man, 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 a 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 asked why Wilson Fisk was not there to explain this himself, Wesley told him he was busy looking at art, which greatly annoyed Owlsley.

War with the Russians
"Masked Vigilanttes, Crazy Russians. I'm getting my stun gun out of storage."

- Leland Owlsley

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 brothers were no longer a part of their organisation 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
"The funds have been reallocated as requested, all the arrangements made as per your agreement with the guy we're not supposed to blah blah blah."

- Leland Owlsley to Nobu Yoshioka

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 Russians. 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.

Taking Precautions
"My son was coming to visit, I had to tell him no stay out of New York Lee, shits going on. I'm 73 years old, you know how many times I have left to see him."

- Leland Owlsley to Wilson Fisk

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 were 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
"I appreciate your support in the matter." "Sure, why not, we're all in this together right? What's left of us."

- Wilson Fisk and Leland Owlsley

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 organisation. 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.

Avoiding Suspicion
"Speak with Gao, if she wasn't involved we might need her support against further unpleasantries." "And if she was involved?" "Then it's been an honour doing business with you."

- James Wesley and Leland Owlsley

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, uhm, shit happens."

- Leland Owlsley to Wilson Fisk

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.

Betrayal Revealed
"But I'm a fair sort, that's why I'm only taking half your money. You go your way, I go mine, not exactly what I'd call win win, but it's as close as we're going to get with this. So, we on the same page?"

- Leland Owlsley to Wilson Fisk

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. 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 where he hit his head hard and was killed.

Personality
"You ever tried put a puzzle together with a piece missing? It's damn aggravating."

- Leland Owlsley to James Wesley

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.

Abilities
"The numbers are like tea leaves. Nobody reads them like I can."

- Leland Owlsley


 * Master Businessman: Owlsley was in charge of finances for Wilson Fisk's operation and was highly revered and successful businessman at Wall Street.

Equipment

 * 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.

Family

 * Lee Owlsley - Son

Allies

 * Madame Gao - Associate
 * Nobu Yoshioka † - Associate
 * James Wesley † - Associate
 * Anatoly Ranskahov † - Associate
 * Vladimir Ranskahov † - Associate
 * Melvin Potter
 * Cornelius van Lunt
 * Randolph Cherryh
 * Murray
 * Schwab
 * Francis
 * Carl Hoffman

Enemies

 * Wilson Fisk - Associate turned Killer
 * Vanessa Marianna - Attempted Victim
 * Daredevil
 * Christian Blake †

Trivia

 * In the comics, Leland Owlsley is primarily known as the costumed criminal called the Owl.
 * Steven S. DeKnight confirmed Owlsley is dead, so his son Lee could become the Owl.
 * Leland Owlsley's plot to murder 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.

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 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.
 * David Shumbris was a stunt double for Bob Gunton in the role of Leland Owlsley.