The Most Messed Up Things Wolverine Has Ever Done

Wolverine might be the gruff, cigar-chomping heart of the X-Men, but let’s be honest:
this guy has done some deeply disturbing things. For every heroic sacrifice,
there’s a moment where Logan’s claws came out at exactly the wrong time, or his berserker
rage turned him into the last person you’d want anywhere near a school full of kids.

Thanks to decades of comics, animated shows, and blockbuster movies, we’ve seen Wolverine
at his absolute best and his absolute worst. The stories below dig into the most messed up
things Wolverine has ever done from accidentally wiping out his own team to crossing some
seriously creepy lines in his love life. Along the way, we’ll look at why writers keep
pushing him into these morally dark corners, and why fans still love him anyway.

Why Wolverine’s Darkest Moments Hit So Hard

Part of what makes Wolverine such an enduring character is that he’s built on contradiction.
He’s a soldier who’s sick of war, a weapon who wants to protect kids, a killer trying to live
like a hero. His healing factor lets him survive anything, but it also means he has to remember
everything every war, every mission, every body.

Marvel creators have leaned into that tension for years. Many of Wolverine’s worst acts happen
when he’s under mind control, trapped in black-ops programs, or pushed into “no-win” situations
where every option is awful. That doesn’t excuse what he does, but it does make his story less
about a perfect superhero and more about someone trying (and often failing) to outrun his own
history. Those failures are exactly what we’re about to walk through.

1. The Night Wolverine Killed the X-Men

The Old Man Logan massacre

One of Wolverine’s most infamous sins happens in the Old Man Logan timeline. In that
bleak future, villains coordinate a massive attack that leaves heroes scattered and overwhelmed.
At the X-Mansion, Wolverine thinks he’s defending his students from a full-on invasion by classic
enemies. He slashes, stabs, and fights his way through a seemingly endless wave of villains
until the illusion drops.

It turns out that Spider-Man villain Mysterio has been manipulating Logan’s senses. Those enemies
he thought he was killing? They were actually his friends. In a horrifying twist, Wolverine realizes
he has just slaughtered the X-Men the only real family he’s ever had with his own hands.
Horrified and broken, he tries to take his own life by lying on train tracks, but even that doesn’t
stick because of his healing factor.

This moment is one of the most messed up things Wolverine has ever done not because he meant to do it,
but because he has to live with the memory. It explains why “Old Man Logan” is so withdrawn,
why he refuses to unsheathe his claws, and why he’s convinced the world is better off without him.

2. Murdering His Own Son, Daken

A family feud with a body count

Wolverine’s family tree is a tangled mess of clones, secret children, and trauma, but his relationship
with his son Daken (Akihiro) sits right at the center of that chaos. Daken is the child Logan never got
to raise stolen at birth, manipulated by the shadowy mastermind Romulus, and molded into a weapon
specifically meant to hate his father.

Over the years, Daken becomes an assassin, a Dark Avenger, and a recurring threat to the X-Men.
Eventually, their conflict escalates to the point where Wolverine is convinced his son will never
stop killing. In one storyline, Logan is persuaded that the only way to end the cycle is to kill Daken
himself. He ultimately drowns his own son, holding him under while Daken struggles, bubbles rising to
the surface as Logan refuses to let go.

Parents make mistakes; Wolverine commits manslaughter. The scene is brutal even by Wolverine standards.
It’s not mind control, not a possessed clone just a father who decides his son is too dangerous to live.
Even in a universe where death is negotiable, that choice hits like a truck, and it permanently stains
Wolverine’s claim that he’s “trying to be better.”

3. The Ultimate Mercy Killing of a Radioactive Kid

When “doing the right thing” is still horrifying

In Ultimate X-Men #41, Wolverine is sent on a solo mission that might be his most morally
disturbing job ever. A teenage boy named Jesse hits puberty and discovers his mutation is basically
a walking apocalypse: his body uncontrollably emits toxins that melt anyone who gets close. By the
time the X-Men locate him, he has already killed his parents, classmates, and neighbors without
meaning to.

Wolverine tracks the boy down to a cave where he’s hiding, terrified of himself. Logan sits with him,
shares a beer, and talks about mutant powers, guilt, and what it means to live with blood on your hands.
The boy talks about all the normal things he wanted racing, college, first love. He doesn’t want to
die, but he doesn’t want to hurt anyone else either.

And then Wolverine kills him.

The X-Men frame it as a gas leak to avoid a human–mutant panic, and Logan walks out alone, knowing
he just murdered a kid who was as much a victim as anyone he accidentally killed. It’s framed as a
“mercy killing,” but it’s also one of the clearest examples of Wolverine becoming exactly the kind
of monster mutants fear humanity will see them as.

4. Being Weapon X’s Favorite Butcher

A past built on torture and black-ops missions

Before Wolverine was an X-Man, he was a living science experiment. The Weapon X program welded adamantium
to his bones, wiped his memories, and turned him into the perfect killing machine. With his healing factor
and combat training, Logan became a one-mutant black-ops squad deployed on missions where the goal
wasn’t rescue, it was elimination.

Various comics and flashbacks show him infiltrating compounds, assassinating targets, and sometimes
straight-up massacring enemy forces. We see hints of torture, interrogations that definitely don’t
follow any Geneva Convention, and entire rooms full of bodies left in his wake. Later, when he regains
more of his memory, Wolverine realizes that a lot of the “classified” things he did were basically
war crimes with a government logo stamped on top.

That’s part of what makes his time with the X-Men so complicated: every time Professor X calls him a hero,
Logan is mentally flipping through a file cabinet full of missions he wishes he could forget. His worst deeds
weren’t just accidents; some of them were paychecks.

5. Creeping on Jean Grey (and a Few Other People’s Partners)

The king of unhealthy crushes

If you ever needed proof that Wolverine has boundary issues, look no further than his long, messy obsession
with Jean Grey. For years, Logan has hovered around Jean while she’s in a committed relationship with Cyclops,
cracking jealous jokes, flirting aggressively, and sometimes outright undermining their marriage.

Comics have retconned things so that Jean has some feelings for Logan too, but that doesn’t change the pattern:
he’s constantly pushing at the edges of someone else’s relationship. It’s not just Jean, either. Early stories
show him fixating on Heather Hudson, the wife of his close friend James Hudson, after they rescue him from the
Weapon X program. Instead of “thank you for saving my life,” Logan slides into “I’m into your wife” energy.

Compared to slaughtering the X-Men, creeping on your friend’s spouse might sound minor, but it reveals a lot
about Wolverine’s darker side. He’s not just violent; he’s emotionally reckless, often using romantic drama
as another way to self-sabotage and hurt the people closest to him.

6. Sleeping with Mary Jane While in Peter Parker’s Body

The body-swap story that aged like milk

In the Ultimate Spider-Man comics, there’s a storyline where Wolverine and teenage Peter Parker
swap bodies because comics love chaos. While Logan is stuck in Peter’s younger body, he has to pretend to
be a high school student, hang out with Peter’s friends, and deal with Peter’s girlfriend, Mary Jane Watson.

Instead of drawing a hard ethical line you know, basic “I’m secretly a grown man in a teenager’s body, maybe
I shouldn’t” logic Wolverine lets things get physical. The story strongly implies that he sleeps with Mary Jane
while still wearing Peter’s face and name tag. When they swap back, Peter is understandably horrified.

Even in a universe full of mind control and timeline hijinks, this one is rough. It’s a violation of consent on
multiple levels and one of the clearest examples of Wolverine being less “tragic antihero” and more “absolutely
not okay, dude.”

7. Stabbing Rogue in His Sleep

Nightmare plus claws equals disaster

The live-action X-Men movies gave Wolverine plenty of heroic moments but they also gave him one of his most
messed up accidents. In the first X-Men film, Rogue checks on Logan while he’s sleeping in the mansion.
He’s having a nightmare about his time in the Weapon X program, thrashing in bed, clearly trapped in a memory
where everything is a threat.

When Rogue tries to wake him, Wolverine snaps awake and instinctively pops his claws… straight through her chest.
She only survives because her power lets her absorb his healing factor long enough to recover. For a terrifying
few seconds, though, Wolverine has literally killed a scared teenage girl who looked up to him.

It’s “just” an accident, but it underlines a scary truth: Wolverine is always one bad dream away from killing the
people he cares about. The movie plays it as tragic, but it’s also deeply messed up that being in the same room
with him while he sleeps is a life-threatening decision.

8. Becoming Apocalypse’s Horseman of Death

Upgraded powers, downgraded morality

At one point in the comics, Wolverine is captured and transformed into Death, one of Apocalypse’s Horsemen.
Apocalypse strips the adamantium from Sabretooth and gives it back to Logan, cranking his physical threat level
to the max while hijacking his mind. As Death, Wolverine turns on his own allies, battling the X-Men with lethal
intent and nearly killing several teammates.

As with many of his worst acts, mind control is involved, but the aftermath is still ugly. Logan has to live with
the fact that, given the right push, he becomes everything the X-Men are supposed to fight a nearly unstoppable
weapon serving an extinction-level villain.

Even after he breaks free, the “Horseman of Death” phase becomes another piece of emotional shrapnel lodged in his
brain. Every time someone worries Wolverine will lose control, that storyline is Exhibit A for why their fear
isn’t totally irrational.

9. Leading Black-Ops Teams That Do the Dirty Work

X-Force and the ethics of preemptive killing

Wolverine isn’t just a reluctant killer; sometimes he’s the guy organizing the kill squad. In several eras,
he helps form and lead versions of X-Force covert mutant strike teams that take on missions too morally gray
for the main X-Men lineup.

These missions often involve preemptive assassinations, targeted strikes, and decisions like “do we murder this
kid now so they don’t grow into a genocidal villain later?” Wolverine frequently signs off on those calls. He
doesn’t love it, but he still pulls the trigger or, more accurately, pops the claws.

What makes this especially messed up is that Wolverine knows exactly what it means to be used as a weapon.
He’s lived it. Yet when the X-Men need someone to build a black-ops solution, he steps up, effectively passing
that same moral burden onto younger mutants like X-23 and others who follow his lead into the shadows.

10. Failing (and Endangering) His “Children”

The collateral damage of Wolverine’s legacy

Wolverine didn’t choose to be a dad in the traditional sense, but he has a whole generation of people tied to
his DNA and his legacy: Daken, Laura Kinney (X-23), and various alternate-universe children and clones. Almost
all of them have traumatic childhoods, brutal conditioning, or life trajectories shaped by the same systems
that broke Logan himself.

While Wolverine isn’t directly responsible for creating X-23, he does become part of the cycle that defines her
life. Laura grows up in a lab where she’s treated like a tool, subjected to torture and a “trigger scent” that
can force her into a killing frenzy. Her most haunting moment is accidentally murdering her own mother under
the influence of that scent a tragedy that mirrors Wolverine’s long history of being weaponized against his
will.

Over time, Logan tries to be a better father figure. He mentors Laura, tries to reach Daken, and builds emotional
bonds with young mutants who see him as a protector. But the body count that surrounds his family proves that
simply trying isn’t always enough. His kids inherit not just his powers, but his enemies, his trauma, and the
constant risk that they’ll be turned into weapons too.

What These Messed Up Moments Say About Wolverine

Put all of these stories together and you don’t get a simple superhero. You get a portrait of a man whose life
is basically one long, bloody apology he can never completely deliver. Wolverine wants to protect people, but
he’s also the guy you call when someone needs to die. He wants to be a good father, but he literally kills one
of his children. He wants to be a better man, yet his past is filled with massacres, black-ops missions, and
deeply questionable romantic decisions.

That’s exactly why readers keep coming back to him. Wolverine’s worst moments don’t erase his heroism; they
complicate it. He’s living proof that being a hero in the Marvel Universe isn’t about having clean hands
it’s about what you do after you realize just how dirty they are.

Fan Experiences and Reflections on Wolverine’s Darkest Deeds

For longtime fans, reading through Wolverine’s most messed up moments is almost a rite of passage. You start with
the cool surface details the claws, the attitude, the healing factor and then the stories slowly pull you into
the emotional wreckage underneath. The first time you see the Old Man Logan twist and realize he killed the X-Men,
it lands like a gut punch. Suddenly, that grumpy old guy isn’t just a cool future version of Logan; he’s a man
living with the ultimate, unfixable mistake.

The same thing happens when you discover his “mercy kill” of the radioactive teen in Ultimate X-Men.
It forces you to ask uncomfortable questions: if there really were no cure and no safe way to contain this kid,
is what Wolverine did unforgivable, or horrifyingly necessary? The story doesn’t hold your hand or tell you how
to feel. It just leaves you alone in the cave with Logan and the silence that follows.

Fans also talk a lot about how Wolverine’s relationships reflect their own struggles with boundaries and regret.
His obsession with Jean Grey, his messy entanglements with people like Heather Hudson, and that disastrous
body-swap situation with Mary Jane all highlight how easy it is to justify bad behavior when you feel lonely,
broken, or convinced you “deserve” something. You don’t need adamantium claws to recognize that pattern; a lot
of readers see bits of their own worst impulses in Logan’s emotional chaos.

Then there’s the family angle. Wolverine’s dynamic with Daken and Laura hits differently if you’ve grown up
with complicated parents or tried to break cycles of trauma yourself. Logan wants to do right by his kids,
but wanting isn’t enough. He makes brutal choices, hesitates at the wrong moments, and sometimes hurts the very
people he’s trying to save. Watching him drown Daken is like watching someone finally confront a generational
curse except the “solution” is just more violence and loss.

What keeps fans invested is that Wolverine never gets an easy way out. There’s no magic spell that erases his
past, no retcon that fully absolves him. He has to wake up every day with memories of the X-Men he killed, the
child he mercy-slew, the son he drowned, and the people he scared or hurt when he lost control. For a lot of
readers, that feels strangely honest. Real life doesn’t always give you neat redemption arcs either; sometimes
you just try to be less terrible tomorrow than you were yesterday.

In that sense, the most messed up things Wolverine has ever done are also the stories that make him feel most
human. We don’t admire him because he’s flawless. We follow him because he keeps moving forward with a past that
would have broken almost anyone else and because, somewhere underneath the growling and the bad decisions,
he genuinely wants to be better than the weapon the world tried to turn him into.