When Black Widow made her MCU debut, she was already an established agent of S.H.I.E.L.D. who is sent to keep tabs on Tony Stark throughout the events of Iron Man 2. From there, Natasha Romanoff went on to become a founding member of the Avengers, with whom she has helped bring the world back from the brink of destruction on a number of occasions. While her powers may pale in comparison to the majority of her fellow Avengers, Natasha has proven herself to be a more than capable spy and assassin — courtesy of training that was forced upon her from a young age.
While her troubled past has only been hinted at in the cinematic world, it's been on full display throughout Black Widow’s long history on the page. Natalia Alianovna Romanova made her debut during the Silver Age of Comics, first appearing in 1964's Tales of Suspense #52. Her first mission was to travel to America and gather intel on Tony Stark. Since then, Natasha's become a lot more interesting than just an international spy who’s easy on the eyes.
Black Widow has a long, dark, and twisting history — which has seen its fair share of iterations and retcons-- but they almost all revolve around her starting as a villain and partaking in some truly wicked missions before she was ever offered redemption alongside the Avengers.
Let’s dig into this super assassin's checkered past and uncover the 20 Most Wicked Things Black Widow Did Before Joining The Avengers.
20 She worked for the enemy
In the Marvel Cinematic Universe, Black Widow’s days as an international spy have largely been glossed over. We know that she was brainwashed and trained from a young age to be an expert assassin working for the Red Room. It’s unclear how much damage she really did before being brought in to work for S.H.I.E.L.D.
However, in the comics, there is no shortage of storylines that show Black Widow working for the enemy of the Avengers and S.H.I.E.L.D. Instead of simply targeting a single adversary, Black Widow is often tasked with gathering intel that will help take down America’s defense system as a whole. Considering that she’s an expert spy who’s been known to deceive others time and time again, it’s a wonder the Avengers ever trusted her to join them in the first place.
19 She lured Hawkeye into evil
In the films, we’re lead to believe that it was Hawkeye who convinced Black Widow to leave her life as an assassin and become an agent of S.H.I.E.L.D. In the comic, this series of events actually worked the other way around.
In her 2004 retconning, Natasha is a brainwashed super spy who was a part of the Black Widow training program. Much like her earliest days in the comics, she’s an adversary to Iron Man who works alongside other spies to try and gather intel on Stark’s defensive weaponry. During the process, she convinces the criminal archer Hawkeye to join her cause. Together, the two repeatedly try to bring about Iron Man's defeat, until a number of injuries eventually leave both Hawkeye and Black Widow vying for a spot on the Avengers instead.
18 She took Tony Stark out to dinner while his lab was destroyed
In her comic book debut, Black Widow is spent to spy on Tony Stark at the behest of her spy agency. She’s partnered with a man named Boris, who are both tasked with traveling to Stark Industries and tracking down a man named Anton Vanko — a scientist who defected from their agency so he could assist Tony instead.
Similarly to Iron Man 2, Black Widow uses her good looks and charm to deceive Tony, who asks her her out to dinner. Meanwhile, Boris is left to have free range of Stark’s lab, where he has his revenge on Vanko before destroying Stark’s factory. It doesn’t take long for Tony to discover that Natalia was in on the plan, but he's so smitten with the spy that he agrees to see her again in the following issue.
17 SHE DESTROYED HERE EX-HUSBAND
In one of her revised origin stories, Black Widow is subjected to an arranged marriage with a fellow spy named Alexei Shostakov, and the two actually turn out to make a great pair. When their feelings for each other become too real, the agency decides to fake Alexei’s demise so both spies can focus on the job at hand rather than their feelings for one another.
While Black Widow continues her work as an assassin, Alexei is turned into the Red Guardian — one of the agency’s top operatives. Later, the agency creates an android version of Alexei, which they use to try and manipulate Black Widow into obtaining intel from S.H.I.E.L.D. Natasha recognizes their deception a mile away, and she decided to eliminate the copy of her former husband instead.
16 Returned to the Red Room
It would be wrong to call many of the deeds Black Widow carried out outright “wicked,” as the character was brainwashed from such a young age. In a lot of ways, she’s not unlike the Winter Soldier or Wolverine — who were both wiped of their memories and programmed to be savage mercenaries.
That being said, there have been a number of instances where Natasha seems to snap out of her brainwashing only to return to her former agency and allow them to manipulate her once again. Whether this is another result of her being conditioned from such a young age or a wish for Black Widow to actually be evil remains unknown. This back-peddaling has certainly resulted in Natasha carrying out her life of crime longer than necessary.
15 She destroyed her own brother
In the black and white limited series Shadows and Light, it’s alluded that Natasha had a brother who went by the name Vindiktor. When the two were children growing up, the building they lived in caught fire and Natasha claimed to have been rescued by her mother. Vindiktor grew up wishing revenge on his sister due to this childhood tragedy, and he would go on to obtain super strength and a suit of armor to help him do so.
When the two eventually crossed paths, Natasha has already been trained as a super assassin and Vindiktor is ultimately no match for his sister. Vindiktor may have had the defeat coming his way, but the fact that Natasha brought about his demise without batting an eye only demonstrates just how disconnected from her emotions she can truly be.
14 She eliminated her best friend
While training as an assassin in the Red Room, Natasha ended up befriending a fellow girl named Marina. The two grew close and would both rise to become two of the most accomplished agents for the organization. In one storyline, Natasha and Marina end up rendezvousing in Cuba to complete a mission together.
However — just as we’ve seen Black Widow fall for any number of superheroes during her spy missions — Marina ended up developing feelings for the man she was supposed to be undercover with. Of course, this didn’t please the Red Room one bit, and Natasha was instructed to eliminate her fellow spy upon completion of the assignment. Natasha may have hesitated, but she ultimately decided to put orders in front of her friendship.
13 She used her relationships to gather intel
It’s one thing for someone like Natasha to use her her charms to exploit playboys like Tony Stark. After all, it’s ultimately the man’s philandering that would gain the spy the access to the man’s private affairs, but it’s another thing entirely to fire up a legitimate relationship with someone and still use it as an opportunity to gather intel.
Natasha has been guilty of this numerous times over, as she’s had relationships with a number of popular heroes, including Hawkeye, Daredevil, Captain America, and Iron Man. While Natasha would go on to develop real feelings for many of these men, she still wasn’t above using the relationship to benefit her spy agency or from trying to convince the superheroes to switch sides.
12 She spied on Tony Stark for S.H.I.E.L.D.
In the MCU, Black Widow’s days as an assassin are still largely shrouded in mystery. When she first strolls onto the scene in Iron Man 2, Natasha is already an established agent of S.H.I.E.L.D. whose days as an adversary seem long behind her.
Following Nick Fury’s orders, Natasha is sent to investigate Stark Industries, where she purposefully makes one of the company’s employees sick in order to gain closer access to Tony. She then uses her charm and spy skills to earn a position as Tony’s assistant so she can gather additional intel. During the process, she annoys Pepper Potts and sets the stage for a fight between Stark and Rhodes. It’s far from the worst thing she’s capable of, but at the time, we're sure Tony didn't enjoy being spied on and manipulated so easily.
11 She stole Spider-Man’s gadgets
Though she was once an Iron Man villain, Black Widow has been known to be the thorn in the side of a number of other popular Marvel heroes, including Spider-Man.
Despite having her own arsenal of extremely impressive weapons — including her Widow's Bite bracelets and knock-out gas — Natasha is always on the lookout for any tool or gadget that could improve her work as an assassin. In one instance, Natasha attacks and subdues Spider-Man before making away with some of his web-slinging tech. As if that wasn’t already wicked enough, Natasha even hurls a few insults at the young hero, proving that she can also trade lines with the best of them.
10 She tried to knock off one of Stark’s business partners
During her debut issue in 1964’s Tales of Suspense #52, Black Widow doesn’t just help sabotage Tony Stark’s lab, she also assists in trying to knock off one of Stark’s business partners, Anton Vanko.
Much like Natasha, Vanko was working for the Red Room before he decided to defect to the other side, taking on the title of the Crimson Dynamo. Therefore, Black Widow and a strongman named Boris are sent to the United States with the task of eliminating Vanko along with Iron Man, who they believe to be his bodyguard. While Vanko and Boris don’t appear to make it out of the issue alive, Black Widow emerges unscathed, setting the stage for her longstanding rivalry with Iron Man.
9 She refused to spy on her former employers
In the MCU, Natasha was a founding member of the Avengers who has remained loyal to the heroes since the 2012 film. Even when the superhero hero team fragments in Civil War, it’s not as if Natasha returns to her evil ways. In the comics, Black Widow is actually an adversary of the original incarnation of the Avengers. While she does eventually go on to join the team as their sixteenth member, she’s been known to betray them on a number of occasions.
The first instance of this came when Natasha refused to spy on her former employers at the request of Nick Fury. This led to her not only parting ways with the Avengers, but S.H.I.E.L.D. as well — paving way for Black Widow’s freelance career.
8 SHE ELIMINATED HAWKEYE'S FAMILY
Black Widow has been closely linked to Hawkeye on both the page and screen. In both mediums, it’s the archer who ultimately gets Natasha to join the good side, and the two have been romantically linked on a number of occasions as well.
True to her spying nature, Natasha has also been known to betray and deceive Hawkeye time and time again. This tendency was taken to new heights in the Ultimates storyline, where the assassin is responsible for the demise of his family. After proving herself to be a traitor amongst the new assemblage of S.H.I.E.L.D. operatives, Natasha and a black ops team eliminate Clint’s entire family, including his wife and three offspring. Even for a seasoned spy, this easily ranks amongst the wickedest things that Black Widow has ever done.
7 She terminated Jasper Sitwell
A top agent of S.H.I.E.L.D., Jasper Sitwell often served as Nick Fury’s second in command — sometimes filling in for the director when he was away on assignment. Sitwell also worked closely with Tony Stark, corresponding over the defense program between S.H.I.E.L.D. and Stark Industries.
Inevitably, this put Sitwell directly into the sights of Black Widow, and during one of her missions the agent and the assassin ended up crossing paths. Though at first Black Widow seemed to snap out of her brainwashed state, this was simply another one of the super spy's acts. Natasha’s main target was Nick Fury. When Sitwell got in her way, she didn’t hesitate to take out one of the organization’s best men.
6 She took out Jarvis
Black Widow’s allegiance and morality have always been a cause for concern. In the Ultimates Universe, the writers gave us the wickedest incarnation of the character to date. In this alternate reality, Black Widow becomes a member of a new, elite team of superheroes. During that time, she also fires up a romantic relationship with Tony Stark — much to the chagrin of Tony’s butler, Jarvis.
The two constantly remain suspicious of one another, until Natasha reveals herself to be a traitor and swiftly ends Jarvis's life. Not only is this a blow to the team, but it takes a heavy toll on Tony as well, who spirals further down into his addictive tendencies after the betrayal.
5 SHE ATE SPIDER-MAN
Black Widow has done some unsavory things throughout her long life in the comics, though none of them have stooped quite as low as man-eating. With both Natasha and Peter Parker taking their superhero names from arachnids, apparently, the writers at Marvel couldn’t help but wonder what would happen if these two characters ever got married.
Of course, this series of events never actually came to pass in the comics. BThe idea did make it into the Marvel What If? series, where it appears as though Natasha made a meal out of everyone's favorite web-slinger. The moment may be far-fetched, but it's far from the first time that Black Widow has gotten the better of Spider-Man.
4 She dispatched a married couple
During the same mission that would find Black Widow taking out her best friend, the spy is also tasked with assassinating a married couple named Jose and Jema Comineza. Allegedly, the couple had intel that Cuba didn’t want to slip out, which resulted in Natasha going undercover to try and obtain the information from the Comineza. When they refused to crack, Natasha employed a number of intimidation tactics to make the couple believe that their cover had been blown.
The Cominezas finally admitted that they were indeed in possession of the secret intel, and Natasha went on to dispatch the couple using her sniper rifle — putting an end to her reign of terror over the family.
3 SHE WAS AN AWFUL FASHION DESIGNER
Falling into the category of more insulting rather than outright wicked, Black Widow attempted to become a fashion designer at one point early on in the comics. This series of events took place when Natasha was working alongside Daredevil. Since Matt Murdock had a day job as a lawyer, apparently, Natasha needed to try her hand at something else as well. However, the expertly trained spy and assassin couldn’t make it into the world of fashion design, which severely undercut the edge that Black Widow had going for her.
To be fair, this was more of an issue when it came to the writers rather than the character — as even the most capable of female superheroes were subjected to their fair share of stereotypes in earlier issues.
2 She used the Avengers name without permission
Of course, not all of Black Widow’s bad deeds occurred prior to joining the Avengers. Even when she is not the subject of some highly advanced brainwashing, Natasha has been known to have her fair share of faux pas. One such instance came when the super spy was actually the only known member of the Avengers.
Natasha attempted to rebuild a team of her own, but she ultimately failed to make a go of it. While it seems highly unlikely that someone with her years of experience wouldn’t be able to sustain the Avengers, the character does arguably work better as a freelance agent. To add insult to injury, Natasha was sued by the Maria Stark Foundation for trying to use the Avengers title — as if the super spy had any regard for the law in the first place.
1 She’s continued to betray the Avengers even after joining them
Black Widow’s worst personality trait by far has to be her inability to stay loyal to anyone for too long. This is no doubt the result of her upbringing, which was filled with brainwashing and spy training. Not to mention that the very nature of her job involves deception and questioning everyone’s true motives.
Even after she defects from her home country and aids S.H.I.E.L.D. and the Avengers, Black Widow has been known to betray her fellow heroes repeatedly. Sometimes this is no fault of her own, while other times it is a simply a reflex of her personality. While this might make it harder to establish an emotional bond with the character on the page, this constant shift from villain to hero is arguably what has made the character so intriguing over the decades.
What do you think is Black Widow’s wickedest deed? Let us know!