Created by the iconic duo of Stan Lee and Jack Kirby back in 1965 – as is the case with so many other classic Marvel characters of that time period - the S.H.I.E.L.D. organisation debuted in Strange Tales #135 and has rarely looked back. Sure, S.H.I.E.L.D. may have varied in popularity over the ensuing decades, but Nick Fury and his crew are always keeping an eye on all happenings within the Marvel universe, even if they’ve not always had their own comic book title in publication.
Whether it was known as Supreme Headquarters, International Espionage, Law-enforcement Division or Strategic Hazard Intervention Espionage Logistics Directorate – or, for that matter, any of the various different names in-between those titles – S.H.I.E.L.D. has often had some thoroughly nasty cookies in its ranks at times.
From out and out villains getting their start in S.H.I.E.L.D., to those driven mad by the technology available to them within the organisation, or even to those corrupted by power and greed, the organisation has had some mighty problematic members over the years. And when such no-good people are working within such a hugely powerful organisation, that spells trouble for the planet and for those who choose to protect it.
Some of this characters may be misunderstood, others may just be pure evil, but they all have their own – albeit sometimes twisted – logic for doing what they do. And so, with that, let’s take a look back at the long history of S.H.I.E.L.D. and its 15 most evil, sinister, calculating, or maybe even misguided members.
15 Tony Stark
Now this one is a little bit of a grey area in whether you consider Tony Stark a truly evil presence. Essentially, it breaks down to what side you were on during Marvel’s initial Civil War comic book arc.
Of course, in Civil War we saw heroes and villains taking sides based on the Superhero Registration Act. Where Stark was concerned, he was given the position of Director of S.H.I.E.L.D. at that point in time, meaning he was heading up the charge when it came to forcing heroes to register themselves and publicly reveal their identities.
Stark was never a full-on evil villain during Civil War, but he was certainly the one positioned as the more villainous when it came to the sides at war during this legendary comic arc. In fact, it was his strong will and pressure that eventually led to Captain America handing himself over, which ultimately led to the assassination of Steve Rogers.
14 Inali Redpath
Once upon a time, Cherokee shaman Inali Redpath fought alongside Captain America, with the pair rescuing an impressive 182 people from a Balkans-based prison camp. This was a man who was a bona fide hero and a man of the people.
Following his apparent death, it was revealed years later that S.H.I.E.L.D. had cloned Inali in the hope of him being a fully-fledged member of their organisation. Because cloning always goes well, right…?
Of course, anybody with any familiarity with comic books knows that cloning is always likely to end up going horribly wrong, and that’s exactly what happened here. S.H.I.E.L.D.’s latest addition was totally unstable, and he’d drug Captain America before launching a hurricane over Miami in order to reclaim land for his Native American forefathers.
During this attack, the Inali Redpath clone ended up killing 147 innocent civilians, once again reaffirming why cloning is never a good idea.
13 Tony Masters
As the villainous Taskmaster, Tony Masters had spent over two decades plotting to kill Earth’s Mightiest Heroes. But that’s all fine and forgotten, for the 2000s saw it revealed that Taskmaster had been a sleeper agent for S.H.I.E.L.D. all along. And, suffering with memory issues, Masters never even knew.
Over the years, Taskmaster had battled the likes of Spider-Man, Captain America, Iron Man, Ant-Man, Daredevil, and near-enough any Marvel hero you could think of. More surprisingly, he’d usually hold his own in battles against these heroes, with his major ability being that he can mimic and master someone’s fighting style merely from watching them in action. Additionally, he also helped to train up budding supervillains.
It was a little far-fetched to see Taskmaster revealed as a S.H.I.E.L.D. agent all along, but having this longtime villain a part of the organisation certainly marks him out as one of the more evil S.H.I.E.L.D. members… even if he didn’t really know what he was doing for all of those years.
12 Natasha Romanoff
Like a couple of other listings in this article, Natasha Romanoff is one where the water is certainly murky when it comes to classing her as either a truly evil villain or an all-out hero.
Whilst more modern comic book times may have seen Black Widow positioned as more heroic, largely due to the popularity of Scarlett Johansson’s big screen Natasha, the comic book Widow has been often portrayed as somebody who can’t be trusted. That’s what happens when you’re simultaneously working for both S.H.I.E.L.D. and the KGB or some other similar organisation.
Black Widow was shown to be a double agent for years, meaning she was an uncertain, shadowy part of S.H.I.E.L.D. when she was shown alongside the likes of Nick Fury and Steve Rogers. Even though it was believed that Natasha was brainwashed into committing acts against S.H.I.E.L.D., that still doesn’t mean that it was necessarily okay.
11 Paul Allen
It doesn’t get any more generic a name than “Paul Allen”, but this S.H.I.E.L.D. agent certainly wasn’t as placid and boring as his name would suggest.
Allen was part of a S.H.I.E.L.D. team that was working on Project: Gladiator – the then-latest attempt to replicate the Super Soldier Serum that had turned Steve Rogers into Captain America – but, as is often the case with this stuff, he secretly had an ulterior motive. An agent of S.H.I.E.L.D. covertly being up to no good in order to serve their own needs? Never!
During his time working on Project: Gladiator, it would be revealed that he was actually working for the villainous A.I.M. group. Being rumbled on that front was bad enough for Allen, but things quickly went from bad to worse when he kidnapped Wilma Calvin – that decision saw Paul killed at the hands of the hulking Man-Thing. Smart move.
10 Edward Cobert
Poor Edward Cobert. One minute a genius S.H.I.E.L.D. agent and scientist, the next minute an aggressive ball of rage with a low IQ.
When working on Project: Lazarus for S.H.I.E.L.D., Cobert made the mistake of testing a superhuman serum on himself. The result saw his size grow but his intelligence drop. Initially called Leviathan, he’d later be known as Gargantua and would do battle with the likes of Wasp, Captain America, Hulk and The Defenders.
It was as part of Doctor Octopus’ Masters of Evil that he really came to the fore, with that team actually targeting the entire Avengers team and the famed Avengers Mansion. Luckily for Earth’s Mightiest Heroes, the Guardians of the Galaxy just so happened to turn up for a far-too-conveniently-timed visit and were able to put a halt to the plans of Doc Ock and his crew.
Soon after this, Gargantua would find himself once more a part of S.H.I.E.L.D. – this time locked up as an inmate at the organisation’s Pleasant Hill community.
9 Erik Gorbo
The no-good Erik Gorbo is one of those who was working for S.H.I.E.L.D. with one intention in mind: use the technology available to him on a daily basis to turn himself into a superpowered being.
And for Gorbo, he’d actually succeed!
Using a serum, Erik Gorbo transformed into the nefarious Monster Ape, a villain who was quite simply a, err, monstrous ape. Yep, this was at a time when Marvel were keeping it ‘does exactly as it says on the tin’ when it came to their characters’ names.
With his new abilities, Monster Ape looked to get up to plenty of shenanigans and crimes that would result in his bank balance being boosted. Unfortunately for him, though, he’d run afoul of Captain America and The Falcon.
Having only debuted in March 1971’s Captain America #135, Erik Gorbo only appeared in one more issue before being killed off.
8 Brent Jackson
As a member of S.H.I.E.L.D., Brent Jackson was sent on a mission by Nick Fury – capture a wrongly-accused-of-murder Wolverine. The thing is, Fury, being the ever-wise guy that he is, wasn’t completely backing Jackson as an agent he could fully trust, and so he brought in outside help to keep an eye on Brent.
Fearing Jackson would actually have Wolverine killed, Fury was right in his suspicions. With Jackson indeed capturing Wolverine, it was soon revealed that he was really working for the infamous Weapon X Program all along. The plan was to bring Logan back to Weapon X at the orders of Malcolm Colcord, with Wolvie in turn then being given to the nefarious Sabretooth.
By the time all of the smoke had cleared, the no-good Brent Jackson actually ended up replacing Colcord as the head of Weapon X, marking him out as one of S.H.I.E.L.D.’s most evil, untrustworthy agents to date.
7 Val Adair
Val’s comic book run may have been incredibly brief – in fact, he only appeared in just three issues – but he has certainly gone down in notoriety.
As an agent of S.H.I.E.L.D., Adair was hired as part of a conspiracy to have Tony Stark assassinated. The initial plan was for Val to force Stark Industries to become a weapons creator once more, but he soon decided that a better idea would be to kill Stark.
Unfortunately for Val Adair, ol’ Shellhead would put a stop to this plan, and Val would end up in prison. Things then took an even more tragic turn for Adair when he was stabbed in the neck and killed during his stint locked up.
It may have only been a brief run that he had, but Val Adair has gone down as one of the most notorious names to have been associated with S.H.I.E.L.D. After all, it takes some balls to try and kill Iron Man!
6 Agent 9
The unknown Agent 9 made just one appearance – turning up in 1998’s Captain America: Sentinel of Liberty #1 – but it was one full of bad intentions.
A supposed trusted, longstanding member of S.H.I.E.L.D., Agent 9 debuted in that issue but he’d not make it out of the comic alive. Like so many over the years, Agent 9 was revealed to be a double agent, this time working on behalf of the nefarious Red Skull.
With a photographic memory, Agent 9 used his skillset to get S.H.I.E.L.D. intel to the Red Skull and his HYDRA cronies. Luckily for the good guys, though, Agent 9’s real MO was soon realised by Sharon Carter, aka Agent 13, who would kill the double-crosser as he attempted to flee to the clutches of the Red Skull.
When it comes to defectors, S.H.I.E.L.D. and their agents certainly don’t mess around or take any chances, as Agent 9 found out the hard way.
5 Blackie Drago
In the Ultimate Marvel world, Blackie Drago is the first man to take on the moniker of The Vulture – in the main 616 universe, Drago is actually the second man to don the wings, following in the footsteps of Adrian Toomes.
Putting a twist on what readers of Marvel’s standard 616 books knew, this version of Blackie was depicted as a former S.H.I.E.L.D. agent who had become unhappy and angry at the organisation. As is ever the case with these things, Drago soon becomes a bad guy, becoming a hired gun and attempting to kill Donald Roxxon.
With a suit given to him by The Tinkerer, Drago becomes The Vulture, although he’s soon taken down by Spider-Man and thrown in a S.H.I.E.L.D. holding cell. That wasn’t the last we’d seen of the “Ultimate” Vulture, though, for he’d escape during a breakout by the Green Goblin. In fact, Drago was part of the Ultimate Six team of villains who helped kill off Peter Parker in the tragic and heartbreaking Death of Spider-Man story arc.
4 Eric O’Grady
Sure, Eric O’Grady may have been the third man to take on the Ant-Man moniker – following in the size-changing shadow of Hank Pym and Scott Lang – but that didn’t necessarily make him a hero.
As a low-level agent of S.H.I.E.L.D., O’Grady happened across Pym’s Ant-Man tech and decided to steal it for his own needs. And what were those needs? Well, largely just creepily shrinking himself down so that he could watch women undressing or taking showers. Yes, this version of Ant-Man was a pervert, even going as far as to have sex with his best friend’s widow on the grave of said friend mere minutes after his pal’s funeral.
Despite being an eerie, darker Ant-Man, O’Grady would eventually redeem himself by sacrificing his life for others. Still, that doesn’t take away from how he has was one of the most creepy and strange characters in the Marvel world and in the S.H.I.E.L.D. organisation at one point in time.
3 John Wraith
In the Ultimate universe, John Wraith is the man tasked by S.H.I.E.L.D. with heading up the Weapon X Program designed to capture mutants and force them to carry out top secret missions on behalf of the US government.
What makes Wraith so evil and messed up, though, is that he was depicted as a completely brutal, sinister and spiteful figure for so much of his Ultimate lifespan. This was never displayed any better than the treatment dished out to Wolverine by Wraith and his men.
With paratrooper James Howlett having had his memories wiped and adamantium bonded to his skeleton, the caged soon-to-be-Wolverine would be tormented and tortured by Wraith and his men, with them taunting him with snippets of his memories and also shooting him on a daily basis, which allowed them to get a sick kick out of Howlett’s healing factor.
As well as this, the “Ultimate “John Wraith has attempted to manipulate and bribe other super powerful mutants to commit heinous acts, such as forcing Jean Grey to kill somebody otherwise Wraith would kill Cyclops. Make no mistake about it, this S.H.I.E.L.D. alum is one sick puppy.
2 Stanley Carter
The Death of Jean DeWolff was one of the standout story arcs of Spider-Man’s ‘80s run. As suggested in the title, the main focus here is on the death of Jean DeWolff, an NYPD Captain and a close friend of the Wall-crawler’s.
Eventually, the villain behind Jean’s death, a rogue calling himself the Sin-Eater, is revealed to be a detective by the name of Stanley Carter. What we’d also learn as the four-issue story progressed, is that Carter was a former agent of S.H.I.E.L.D. who had suffered some severe side effects from experimental drugs given to him by the organisation.
With increased strength and endurance, Carter became unhinged and violent, especially after he saw a colleague killed in front of his eyes. From that day on, he vowed that sinners would pay for their crimes with their life.
As well as killing Jean DeWolff, Carter also attempted to kill Matt Murdock, Betty Brant, and Spider-Man, not to mention killing several other background characters. Interestingly enough, it was Peter Parker’s public reveal of Stanley Carter as the Sin-Eater that ruined Eddie Brock’s journalist career, for it rubbished previous Sin-Eater articles done by Brock, which in turn led to Eddie’s hatred of Peter and his eventual bonding with the Venom symbiote.
1 Norman Osborn
The former Green Goblin, Norman Osborn perfectly manipulated the post-Civil War landscape at one point in time.
After Civil War saw heroes battling heroes, with Tony Stark heading up S.H.I.E.L.D. in enforcing heroes to register themselves, all went sour when the Skrulls managed to infiltrate the Stark-led S.H.I.E.L.D. As such, Stark was held accountable by the government and S.H.I.E.L.D. was deemed no longer effective.
It was here that Osborn would convince the US government to let him step in and take over from Stark, and so Norman briefly became the Director of S.H.I.E.L.D. The reason that was so brief, though, was that Osborn quickly replaced S.H.I.E.L.D. with the H.A.M.M.E.R. organisation, and he also took on the mantle of Iron Patriot.
Whilst Osborn played up that he had the world’s best interests in mind, it would soon become clear that he really wanted to access the post-Civil War files that detailed every heroes real identity. As ever with Norman, evil acts were the real order of the day and he’d even end up pairing H.A.M.M.E.R. with other nefarious organisations in the form of A.I.M. and HYDRA.
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