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In Marvel Comics, Kingpin is one of the most well-known villains among fans. Ruling over New York's criminal underworld with an iron fist, he is known to have many close allies who are extremely loyal to him. However, he is also known to have those close to him who have stabbed him in the back many times. One of these people just happens to be Leland Owlsley.
In Marvel Comics, Leland Owlsley, aka The Owl, was a character created by Stan Lee and Joe Orlando, and he first appeared in Daredevil #3 in June 1964. One of the earliest Daredevil villains, he was a ruthless financier who had his own criminal empire and is known to have had a few run-ins with the Kingpin as well. Not only that, but he also made plans to replace Wilson Fisk as the Kingpin of New York.
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However, this only got him into more trouble.
Leland Owlsley's coup to become the new Kingpin ultimately failed in Marvel comics
In Marvel comics, Leland Owlsley decided to pursue his most ambitious plan yet, which involved replacing Wilson Fisk as the new Kingpin of New York. He started this by bringing in Doctor Octopus into his plan—but Otto wasn't interested in pursuing this with him, and the two were then interrupted by Spider-Man. However, they both ran away during the fight.
Owlsley was later on attacked by Octopus himself and was brutally defeated by him. Otto ended up breaking his claws and braces and had him sent to the hospital in prison as his injuries were too grave. However, during his time in prison, he was given many experimental drugs, which made him even less human, and once he got out of prison, he was still obsessed with becoming the new Kingpin.
So, he recruited Stilt-Man, Gladiator, and Copperhead to form a new gang so that they could assassinate Wilson Fisk. However, Copperhead betrayed everyone, and she planned on harvesting the souls of all the members of the gang. This led to Owlsley seemingly sacrificing himself and attacking Copperhead, thus ruining his plans in Marvel Comics.
Leland Owlsley has also betrayed Kingpin in the Daredevil show
Even aside from being a crook in the Marvel comics, Leland Owlsley also had quite the run on Marvel and Netflix's Daredevil series. In the show, the character was played by actor Bob Gunton and was portrayed as a crook who was working for Wilson Fisk. He was an accountant for the Kingpin and part of Silver & Brent, who managed all his finances.
However, aside from being the more monstrous version of the character portrayed in the Marvel comics, the character here was a more grounded being, and he ultimately betrayed Fisk in the highest order too. After Fisk fell in love with Vanessa, Owlsley believed that she was bad for business and was turning the Kingpin soft.
So, he then conspired with Gao to kill her, but she wouldn't join him in the plan as she had to leave New York. He then attempted to blackmail Fisk, but the Kingpin wasn't having it and threw him down an elevator shaft. Looks like Owlsley has bad luck in every universe.
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