Since he’s probably Oswald’s closest Marvel equivalent, being a relatively-unpowered crime-boss who semi-frequently becomes Mayor… any thoughts on Wilson Fisk, the Kingpin of Crime?
It's a comparison that's frequently made by Big Two fans and it's easy to see where it comes from, certainly they're the most iconic gangster/mafioso villains in their respective companies, but I don't think Kingpin is the closest Marvel has to Oswald because A: If anyone has a prior claim on Comic Book Gangster, it's definitely him, and B: They simply don't work in comparable or equivalent fashion. You can even boil down a key difference to the fact that The Penguin is inherently a small man trying to be bigger, and The Kingpin is the biggest man who ever lived. That's not a joke about their sizes, that's how they operate as characters and villains: Oswald is underestimated, ridiculed, diminished, and driven in large part because of it. He is the underdog, he slips under the radar, he slips through the cracks, he is a cockroach who lives to thumb his nose and pull the rug under the bigger bastards who think they can step on him. Wilson Fisk IS the bigger bastard who steps on people, he is the biggest bastard in the world.
He is an unsurmountable force of crime at the top of every possible advantage that a criminal can possibly weaponize, he is a titan of wealth and privilege as willing and capable of crushing your skull with his bare hands as he is of murdering your entire social circle with a phone call. He is "the ill intent", the biggest and strongest gangster of all time, and even if there are bigger and stronger bastards than him, they certainly aren't gangsters like him, they certainly aren't meeting him in his playing field of choice. There isn't really a DC equivalent to Wilson Fisk - there were certainly attempts to make Luthor and Cobblepot more like him, there's no shortage of imitators or knock-offs like Blockbuster and Tobias Whale, but the Kingpin is a league of it's own among comic book gangsters. Like Luthor and Joker and Doom, like the top dogs of the genre, he's become an Archetype in his own right.
I talked about his Spiderverse version a little while back in regards to how much I liked him in that movie and what his design represented about him, Fisk as this black hole obelisk who drains the color of every room he's in and suffocates the world visually as well as metaphorically, far from the most interesting character in the movie but one that you can pin all these other more interesting things on, and I think that's also applicable to a lot of what he does as a Spider-Man villain. Now, he's a GREAT Spider-Man villain, easily one of the best, his arcs in Ultimate Spider-Man alone should be more than enough proof of concept for that, but even if he's not necessarily the most colorful or intimate or dangerous villain to hang a Spider-Man story on, he is maybe the most villain to hang a story on - the entirety of Marvel's street level vigilantes and organized crime exists under his shadow, and you can blow up his scope to the moon and back as a way to build up all the other characters you can squeeze more dramatic stuff out of. Whether it's in TAS, where he is so undisputably atop the pecking order that everyone else is bouncing off his fixed presence, or in the Insomniac games, where he stood tall as Peter's main villain for 7 years until the game begins with his downfall as a way to kick off all the strange new threats he'll be up against, Wilson Fisk is The Crime Man to rule all Crime Men, as entrenched and emblematic and secure in his kingdom of Manhattan as Dracula is to Transylvania and Dr.Doom is to Latveria.
Unlike the vast majority of Spider-Man villains who regularly enjoy redesigns and rewrites and do-overs, official and fan-made alike, Wilson Fisk is practically the same character in every iteration, there's very little need to seriously rethink or readjust who he is and how he does things because he is perfectly simple and perfectly timeless - we have now two Ultimate Spider-Man comic runs that have brought significant overhauls and revisions and new spins to established Spider-Man characters, and in both of them, Wilson Fisk is a major character, and he is completely and utterly unchanged from how he already works in the mainline universe. Even if you don't want to use Wilson Fisk, you can't neglect Wilson Fisk, you have to show how he fits into things, you have to show what he's up to or how he allows or makes way for what's happening without him, you have to give him his cut. This imutability of his is another thing I'd say is a major difference between him and Penguin - Oswald demands change, he demands growth and adaptability, he demands different surroundings more suited to him, he wants to grow and grow and make a nest that's suitable for him, he can't fit into existing systems so he breaks them to remake them as his own. That is simply not the case with Wilson Fisk.
Unlike The Penguin, unlike some of the other great comic book supervillains, Fisk has no intention whatsoever to change anything about how the world works - as far as he's concerned, it worked just fine up until these costumed irritants arrived, and even they just became another part of his conglomerate in time. Fisk really doesn't have or need any kind of big philosophy to justify himself, rather, he takes it as fact that he's operating under the way the world works and under a merit he's achieved by being the man he is. He is content within society's morality, because he is at the top of society and therefore that morality will always bow to him. The legions of costumed enemies orbiting his life are merely dissidents going against the order of things that places him at the top, tools to be used and bugs to be squashed and little more.
And this is true even of those whose power and scope stands above his own - they are not players in his game, and if they are, they are distractions, diversions, things that he can deal with. When he loses to billionaires like the Stromms in Zdarsky's run, when he has to playy ball with bigger villains, when he is ousted in a power play, it is humiliating, and he doesn't deal well with humiliations - but he can take humiliations, he knows he can give back, he can ultimately rebuild his pride as he rebuilds his empire time and time again. Spider-Man is annoying and powerful and infantile and annoying and an enemy and really really annoying, but he is no existential threat. He is not terribly concerned about Spider-Man, which is part of what makes him such a fun Spider-Man villain, that he never sees it coming when Spidey gets serious and just brings him down (peak example of this being Back in Black), that he is this larger-than-life bully/shitty grown-up who actually can and must be defeated. And if a lot of what makes him a fun and great Spider-Man villain is contingent in the ways that he doesn't lose sleep over Spider-Man, part of what makes him a stronger Daredevil villain is the precise opposite: he desperately wishes he could be this dismissive towards Daredevil, who is for all intents and purposes weaker than Spider-Man. It's his relationship with Daredevil that brings out the best of him as a villain and the worst of him as a person alike.
Against Spider-Man, the Kingpin is a very strong enemy, the figurehead of the kind of crime that is Spidey's daily routine, a powerful and oppressive force ruling over NYC who is nevertheless a step down from the Green Goblin or Dr Octopus or the Symbiotes and all those other genetic nightmares and obsessed masterminds that plague his life. No matter how clever or vile his schemes are, Spider-Man can still beat them, and Spider-Man can ultimately always triumph over him in a fight, and Fisk can always rebuild because Fisk builds empires as easily as most people breathe, and things rarely if ever get personal between him and Peter. Against Daredevil? There IS no bigger threat than Kingpin (well, The Hand I guess, but they're boring as shit), Kingpin is the mountain that Matt always crashes against in due time, and it is always personal. The Kingpin is his biggest and strongest enemy, able to run mental laps around Matt and someone that Matt cannot in fact beat in a fight, their battles are drawn out miserable slugfests where Fisk usually thrashes him around like a ragdoll with few conclusive victories and whatever victory Matt has is hard-won and usually via cheap shot.
Matt has an infinitely harder time dealing with Fisk than Spider-Man does, which is part of why it is Kingpin's appearences in Daredevil comics that made him comic book villain royalty: Matt has no real advantage against him other than his senses. He has no intellectual advantage, no physical advantage, and he can't even claim to be more determined or driven, Fisk is fueled by an equally horrendously powerful will and protectiveness towards what belongs to him, This City. There is nobody and nothing in the world that Matt hates more than Fisk, and there is nobody and nothing in the world that Fisk hates more than Matt. They've taken turns shattering each other to the point that those slugfests are the least of each other's offenses against each other.
Even besides the sheer accumulated history they have against each other, it's in the way they unforgivably violate each other's vision of the world. If the Kingpin was the invincible man of vision who loves the city and must steer it even if smaller people disagree with him, if he was truly so secure and untouchable at the top of the world, he wouldn't be having such a colossal hard time dealing with this one guy and he wouldn't be reduced to a base animal thug every time he shows up, let alone lose and be humiliated. If Wilson Fisk was as correct as he needs to be, if the strength of his love for Vanessa/the city/what belongs to him was as powerful as he wants it to be, Daredevil would never get the upperhand on him.
And if Daredevil is a man who dedicates himself 100% all the time to protecting the city and it's people, if Daredevil commits unlawful deeds to preserve human life and fight for justice, if Daredevil struggles with the innate contradictions and hypocrisies and nature of what he is and does but can nevertheless push past them all to do the right thing for others, every second the Kingpin lives, every second Fisk lives because he lets him, chips away at the assurance that he's doing the right thing, that he isn't just wasting time. If Daredevil's vision of the city was correct, if Daredevil was right about his beliefs and worldview, there wouldn't be a Wilson Fisk out there getting away with the things he does. They hate each other for that same fundamental reason: If the world was ruled by the principles I need it to be, in order for me to be who I am and do what I do, you wouldn't exist, and you wouldn't be in my way again and again.
As a Spider-Man villain, he is one of the greats, a core component of his world, a highly versatile and even necessary figure to have and an excellent villain to dictate proceedings. As a Marvel Universe villain, he is an indispensable facet of any criminal element, the Mt.Fuji that the streets of Marvel rest upon, someone who can be added to any storyline and be grafted into many characters to oppose or assist them, or even create and kill them. As a Daredevil villain, he is undeniable as one of the top supervillains, bordering on main character a lot of the time. An implacable unstoppable force of nature as well as a villain of history and brutality and drama and a character who brings intrigue and tragedy and even complexity, even as it all ultimately comes down to that raw hatred between them, the splinter in each other's eye, an infection in their world that just keeps taking and taking and taking without stopping.
It is an unforgivable offense to Wilson Fisk that there is a man out there so beneath him that he cannot break, cannot bend, cannot stop, and who makes such a mockery of everything he's built himself to be by existing, just as it is unforgivably offensive to Matt Murdock that there is a man out there named Wilson Fisk who thinks he has the right to be who he is, and do what he does. To be a man who not only cannot care about human life in any capacity other than what he thinks belongs to him, but whose continued existence attests to a world that validates him, that doesn't care about those lives either, where there is no accountability and no justice and no salvation that cannot be bought and sold. Fisk isn't just an embodiment of cruel, bottomless indifference, he stands for a world that agrees with him.
It would take too much work to defeat him, he just walks unscathed if you do, and even if you defeat him there will just be someone else to step in temporarily. And so it is with a heavy heart that the people of New York accept that the blood of countless runs through the streets, so long as the big man gets to give them their cookie at the end of the day for their hard work and agreeability. He is too big, too clever, too strong, and too invincible - and that's why Peter needs to stop him, that'd why Matt can never stop trying, that's why they can never let him be, otherwise Marvel New York would just be regular New York.
They'd have to accept a world where Wilson Fisk gets away with everything, and who could live with that?
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