Deadpool vs Kingpin Guide

Hitman VS Crimelord

Deadpool VS Kingpin almost seems to write itself. One is often a paid assassin, and usually by the government of whichever country he is in. The second runs one of the biggest crime syndicates in New York City and has hands in crime enterprises worldwide.

It must only be a matter of time before Deadpool gets a contract on Kingpin…except he never did. In fact, he became an anti-hero and more of a do-gooder as the years went on and his popularity grew. Meaning that the likelihood of him ever getting paid to take out the King of Crime became less and less.

They have had ties, albeit very few, and are connected in some unexpected ways. More importantly, many of the audience may not know how brutal an enemy Kingpin can be in physical combat. 

In this versus article, we will explore exactly how close of a fight this would be, their shared history, and finally put them together in a hypothetical battle to claim a victor. 

Tale of the Tape

 Deadpool, AKA Wade Wilson

  • Abilities: Super Fast Regenerative Healing, Slightly Increased physical attributes, including enhanced strength, toughness, peak human speed, and agility. 
  • Most Impressive Victory: I’m going with The Hulk. This particular victory is impressive because he has no healing factor or powers during the fight and has to rely only on dodging and skills(which is essential against Kingpin). Eventually, he leads the Hulk to impale himself so he can steal some of Banner’s blood and get the hell out of dodge. 
  • Brutal Defeat: I’m going with Moon Knight because Deadpool has all the tools to win this fight but doesn’t just lose the first round because of getting distracted, loses round 2 after luring Moon Knight into a carnival House of Mirrors. Moon Knight shattered the mirrors and slashed the hell out of Deadpool, leaving him for dead. 
  • Characteristics: Always cracking jokes, actually insane, a decent sense of loyalty, breaks the fourth wall.
  • Main Advantage: His healing factor will play a massive part in a fight like this. His agility and creative murder strategies will assist in this fair fight.

Kingpin, AKA Wilson Fisk

  • Abilities: Enhanced Strength, Extremely Durable, Peak Reaction Speed, and Superior Intellect.
  • Most Impressive Victory: Captain America. You read that right. Captain America once stepped up to the Kingpin only to get taken out in single combat and nearly crushed in a Bearhug before The Falcon made the save. 
  • Brutal Defeat: Daredevil beats Kingpin to a beautiful bloody mess on a few occasions. Perhaps my current favorite is their alley fight at the end of Season 1 of Daredevil, now on Disney Plus. 
  • Characteristics: A keen intellect, a formidable hand-to-hand combatant, calm and yet capable of psychotic episodes which seem to enhance his basic abilities.
  • Main Advantage: Kingpin is deceptively fast. His massive strength and durability aren’t as magical as other mutations. He is a heavy boy, and that weight is all muscle. This has given him the edge in one on one combat against seemingly physical equals. 

Typhoid Mary

Deadpool and Mary
Deadpool and Mary

In Daredevil/Deadpool ’97 Annual, Deadpool and Daredevil team up to go after a certain Crime Lord. During this longer than your average comic(it’s a good read, I highly suggest it), we learn more about Deadpool and his ‘real’ feelings.

Deadpool is trying to convince Daredevil to take it easy, in a sense, on the one and only Typhoid Mary. For those of you who don’t know this excellent Daredevil villain, she is a sword-wielding, badass woman who suffers from serious identity problems. She deals with ‘Multiple Personality Disorder’ due to a traumatic past caused indirectly by Daredevil. 

Deadpool, seeing some obvious similarities, connects with her almost instantly. In fact, the two are in a pretty heated relationship during this time in comics. He suffers from some mental instability himself, as it were. He betrays Daredevil in favor of this multi-faced maiden for what is a very well-written conclusion.

Why is this relevant? Ha, ha! Guess who happens to be Kingpin’s wife in the current comic cannon(2022). That’s correct. 

Kingpin eventually marries Typhoid Mary. A storm is brewing.

Spider-Man

As much as Daredevil is tied to Kingpin, so is any hero in New York, especially the most famous. The Friendly Neighborhood Spiderman. Spiderman has beaten Kingpin, but it is almost always a temporary win. Kingpin has overcome the Wall-Crawler time and time again. 

Even in the famous 1990s Spiderman cartoon, Kingpin is shown to always be steps ahead of the Wall-Crawler. Like Luther is shown to be with Superman. Unlike the ladder, Kingpin has defeated a Spidey Sense wielding, super strong, mutant-like Spiderman in a fight on more than one occasion. 

Deadpool and Spidey have a long-standing love-hate relationship. Deadpool loves Spidey, Spidey hates Deadpool(but not really). This means that we can possibly take it lightly that Spidey has won nearly every confrontation he’s had with Deadpool. Yet, it is a stark contrast between Kingpin and Deadpool. It is also interesting how this mutual connection hasn’t caused them to cross paths even more.

Toe to Toe with the Kingpin

Toe to Toe with the Kingpin

I want to take this time to bring to light some of the Kingpin’s victories over two heroes who have a similar fighter ranking as Deadpool. Captain America and The Punisher. 

These examples are subtle reminders that Kingpin should always be considered one of the best Villains in Marvel. He likes to live a comfortable life and will kill, plot and murder to keep it. He will also fight, and he is damn good at it.

In Captain America #147, Kingpin, in one of his traditional suits, had an all-out, multi-page brawl with Captain America. 

Foolishly treating the King of Crime like a usual lackey, Captain America learned Fisk would go blow for blow. Not only this, but every strike Steve Rogers landed, Kingpin had an immediate answer for. Eventually, he had the Avenger clasped in a life-ending bear hug had it not been for Falcon making the save.

The Red Skull. In Captain America #378, Kingpin and Captain America’s nemesis also went toe-to-toe. The difference here is now Kingpin was fighting someone willing to kill him. Someone who had the same abandon when it came to the life of his opponents. The end result, Kingpin nearly kills him before Red Skull admits defeat. 

It’s a fair fight, too, as honest as possible. The two big bosses went at it in a stadium in their literal underwear to make a point. Kingpin made it. 

Deadpool and the Big Guys

Deadpool and the Big Guys

Now, Deadpool has taken on several enemies the size of Kingpin. Stronger than him even, and he’s done okay. 

I’ve gone on in some articles about his fights with The Hulk. So this time, let’s talk about some other clearly stronger than Deadpool enemies that he has taken down. 

Sabertooth. In 2016, in Deadpool #8-12, Sabertooth was trying to redeem himself. Wolverine had passed away, as it were, and Sabertooth took his role on the X-Men of all things. Deadpool didn’t care. He believed Sabertooth was responsible for killing his parents and was out for revenge. 

To be fair, there is the context here in which Creed(Sabertooth) didn’t really want to fight. It’s still an evenly matched, bloody mess despite Deadpool bringing weapons which initially ends with Sabertooth shoving Wade into a moving car and passing out. 

In the end, though, it’s Deadpool who outsmarts, outmaneuvers, and takes down Sabertooth. Tying him between a truck and a tree after winning. He even came up with a foolproof plan to kill the healing mutant. 

In Deadpool #66 (June 2002), Deadpool gets a job collecting Rhino’s horn. I admit I chose this particular fight because I love the cover art. You can see it in the link, but I also chose it because Deadpool does not win a clean battle. 

This seemingly sporadic fighter almost always has a plan. Against Rhino, he mostly just runs and avoids being smashed. Rhino does catch up and beat Wade around until Deadpool manages to spray some shrinking Pym-like particles on Rhino to turn him mini. Again that’s how he wins, showing that he knows his limitations.

Things to Consider

Kingpin's Composure is Legendary
Kingpin’s Composure is Legendary

Both of these fighters are more than just brawn. They are constantly shown to overcome issues with one another based on planning far ahead of their enemies. 

Coming into this conflict, I have to wonder how long the fight will go on? Do I give Wilson Fisk a win at the first knockout, or are we going to the death? 

Stripping them of their weapons and seeing who can take down who seems like it favors the Kingpin heavily. 

We’ve seen Deadpool get back up from being cut wide open in seconds during a heated confrontation and even grow back fingers in a minute when severed. Yet, does he even possess enough power to hurt Kingpin? Kingpin has taken direct hits from Spiderman, and when Daredevil wins, it’s usually only by multiple hits with steel batons. 

Let me dive into their current film portrayals before I start the fight.

In the eyes of many fans, these actors have brought to life the best live-action versions of Kingpin and Deadpool. I would be remiss not to consider these versions of the characters in my Final Verdict.

Film and Television

That’s…Ominous.

Ryan Reynolds plays the Merc with the Mouth in Deadpool 1 ad 2. No, no other movie, don’t bring any up. Oh, there will be a Deadpool 3. You must mean that one.

Nearly all his skills from the comics are present in this form. His wit, his humor, and his incredible skills with multiple weapons. He heals from any wound, but he isn’t as always good at planning as his comic counterpart. 

Michael Clarke Duncan was an excellent Kingpin in the movie Daredevil. I stand by that. He even embodied much of the character’s strength and beat the crap out of the hero of Hell’s Kitchen. It is, however, Vincent D’Onofrio who played the Kingpin the longest.

The first season of Daredevil is as much watching Wilson Fisk become Kingpin as it is watching Matt Murdock become Daredevil. It is brilliantly done. What does not seem to be present in this version initially is Kingpin’s super strength or durability in the comics. His fight with Daredevil at the end of season one is still a good scene.

He is shown as very strong and capable, but he does not come off initially as superhuman. However, whether Kingpin’s strength is superhuman is actually often debated. The official Marvel site does list it as so. 

If you saw Hawkeye, like me, you are probably hoping the terrible idea for Kingpin’s fate at its end was a tease and not a final round for the villain. Vincent reprises his role in this show, but something is different. Kingpin seems larger and possesses that fabled strength and durability his comic book version does. So, he may become the powerhouse that heroes should be more cautious of in fair fights in the MCU. 

Final Verdict

Walking into an arena with no interference for a one versus one brawl to end it all. Deadpool and Kingpin come to kill. To make this more interesting, let me avoid what is an easy win for Deadpool and not have him snipe, shoot in the head right away, or some similar tactic. 

To make it not an easy win for Kingpin, who would break the rules if he assumed Deadpool would do this, let’s not have him have his cane fire a laser(it’s a thing it sometimes does). Also, no field laced with explosions or snipers from far off to attack Deadpool. 

No really, in their underwear.

No, these two, to settle this, are doing it Red Skull VS Kingpin style. Underwear fight in the park with no weapons. This is the hypothetical combat I will tackle between these popular comic characters.

From some of their past brawls, we learn that the beginning of this fight is possibly incredibly short. Kingpin takes over right away. Kingpin’s size, deceptive speed, and how his body type protects him from almost all basic blunt damage will put Deadpool in a bad place. 

However, Kingpin’s strength is not superhuman to the level of someone like Rhino or even Spiderman. It’s higher than Captain America, which is a feat, but Deadpool can take whatever Fisk dishes out. He heals.

These two characters play for keeps. The goal for Fisk is to crush Deadpool via a bearhug or some similar attack as quickly as possible. He wants to incapacitate him. So, suppose Fisk can incapacitate Deadpool as he has with Captain America or Red Skull. In that case, he may then try to bury him or bind him and toss him into a ravine of water. 

I don’t think this is going to go well for Kingpin. Previously Deadpool has been pit against an enemy who heals faster and has too many damn senses and a similar skill set. Or even pit against one of the most powerful villains in the Marvel universe. He was screwed from the get to. 

When Deadpool sets out to kill someone with no weapon that he knows is as challenging to take down as Kingpin means, he goes in as he does with any of these fights. Plan in tow. Unlike previous battles, this plan very much can rely solely on the skills available to him.

This time around, Kingpin is a worthy opponent in fisticuffs. Still, Deadpool’s plans to murder are always solo and very effective. Having to rely solely on his own hands, Kingpin would likely never choose to go toe to toe with an assassin like Deadpool without the element of surprise in his favor. 

Deadpool can also get under anyone’s skin, chatter and bait, and Kingpin and Deadpool end up in a much longer, drawn-out fight than Kingpin wanted to get in. Not to take any shots, Wilson Fisk has excellent stamina.

Still, Wade heals and is ultimately an expert striker means that after a few hours of leading the big man around with insults and strikes, this fight ends. How? With Deadpool being his nasty creative self. 

Ala, using Kingpin’s own tactic against him after wearing him down.

What do I mean? Deadpool may take a long time to cause physical damage to the King of Crime’s exterior via punches and kicks or even pressure points. BUT! Deadpool heals, which means he could break his bone and rip it out to jam the sharp edge into a Kingpin. Kingpin is going for that crushing strategy, forcing the two to be close and getting himself stabbed by a man he falsely assumes has no sharp objects. 

Weakened and tired from the long fight, Kingpin would begin fading from the blood loss, not the pain. Wilson Fisk has incredible pain tolerance. His final throw of the Merc with a Mouth would likely break some bones, but Deadpool gets up, mostly healed, to see the last gasps of one of the best villains in the Marvel Universe. 

Deadpool moves over the body to finish the job, hand into the open wound, and crushes an organ. I give this VS fight to Deadpool eight out of ten times. Losing only in the unlikely event he is caught and crushed early on. 

I want to mention that if the cinematic versions of these two were to fight, Deadpool would generally win that fair fight every time. It would still hurt, though. Fisk is never a pushover. 

Trivia

  • Check out Season 2, Episode 6 of Daredevil, for a great confrontation between The Punisher and Kingpin.
  • Kingpin once stole The Symbiote(of Venom) and shot Eddie Brock.
  • In Superhuman Civil War, it was Kingpin who exposed Spiderman’s identity.
  • Kingpin once controlled Ghost Rider.
  • Deadpool does not like Daredevil much. Their crossover comic in ’97 is specifically because of how Daredevil talks down to him.
  • Apparently, Deadpool and Spiderman watched Batman VS Superman together. This is canon in the comics.
  • Deadpool has posed as Peter Parker and Spiderman on multiple occasions.
  • Deadpool joined the Uncanny X-Force once when the team was being paid by Angel but refused the payment. Doing it solely for the cause at the time. 

FAQs

Question: Who’s Stronger, Deadpool or Kingpin?

Answer: Kingpin is clearly the stronger of the two.

Question: Has Deadpool ever Been Paid to Kill the Kingpin?

Answer: Funny enough, I couldn’t find any instance of this. Don’t expect it not to happen, though, as the characters have come back into popularity, and their connection with Typhoid Mary and Spiderman are both excellent writing fodder.

Question: Has Kingpin Ever Hired Deadpool?

Answer: It seems so. Though it doesn’t seem to be in a panel, they speak as if they’ve had a business relationship in the past when they first meet. So, while speculation is pointed towards yes, we haven’t seen a transaction outright. 

Question: Could Deadpool Kill Kingpin?

Answer: Yes, Kingpin is ultimately still just flesh and blood. It would be much harder for Kingpin to truly kill the immortal Merc with a Mouth.

Question: Does Kingpin Have Superhuman Speed?

Answer: No, but his giant body is stated as being only 2% body mass, so that dude can move! He is a formidable foe for any combatant in Marvel. 

Conclusion

This would be one of the more enjoyable panels to read in comic books. These two always dance around the same circles and are great solo combatants. Ultimately, Deadpool’s profession and his Healing Factor force me to give him the advantage, but Fisk should never be underestimated. Also, finally, Deadpool won’t fourth wall attack me. 

I hope you enjoyed the read and check out some of the material linked. We enjoy sharing the history and lore before comparing iconic comic heroes and villains here. There is only love for both characters involved.

Kingpin deserves respect for his skills and long-term win-loss records. Deadpool is just the better killer, hands down. 

Take care, true believers.

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