"Bad, but not too bad" historical figures for an AH project

It's coming down to final projects and such for a lot of my classes (hence why my timeline suddenly slowed down). One of my classes has a very peculiar final: I have to pitch a film.

Now, I'm putting a ton of effort into this because two people have gotten something out of this project (one now writes sitcoms in Canada, another is in negotiations to get his pitch made into a feature film with Universal Pictures).

My concept is pretty simple: A "The Avengers" type film but with historical assholes (secondary or tertiary level bad guys). I don't want to get too heavily into the concept, but it boils down to "Richard Nixon tells historical assholes to work for him and live a decent life, or they can go back to death row."

This is teetering on ASB (and in some regards may overlap, but none that will effect the conversation), but I need some help.

So I'm looking for people who are "bad" or criminals but at the same time probably wouldn't offend anyone from the late 40s to the late 60s.

Preferences:

A. People who are supposed to be dead, in prison, or living in recluse.

B. People with specific skills that make them good for covert operations (Not just good at say, killing people. Things like espionage, leadership, communications expertise, demolitions expertise, ability to fly a plane, etc.)

C. You could see them accepting an offer like this if the alternative was death or life in prison.

D. I want multiple levels of recognition. Some people for people that aren't that well versed in history, others for "nerd points" that your standard viewer might not know.

E. My idea for how the story is told amounts to "Zack Snyder gushing all over a hybrid of the Coen Brothers and Quentin Tarantino", so the people can be unlikable and flawed, but must compensate with badass.

I have a list of figures I'm planning on including, but I'll hold that off for a later post.

I'm not going to say there's a good chance of something coming out of this (I don't even know if my professor will like it), but I want to hand in the best damn pitch I can and see what happens.
 
- Cao Cao, villain of the Romance of the Three Kingdoms.
- Charles Ponzi, the quintissential con man.
- Nestor Makhno, anarchist bandit of Ukraine.
- Mata Hari, alluring WWI spy.
- Catherine the Great, warmongering Russian Tsarina.

EDIT: Sorry, missed "late '40s to late '60s".
 
I know he's not, like, a mass murderer or an extremely powerful figure or anything, but how about D.B. Cooper? You could just ignore all the theories about his identity and make one up. Essentially he'd be an expert at blending in and disappearing after finishing a job. Lots to work with there, I think, and he's just popular enough that people would be like "Oh, yeah! The guy who jumped out of the airplane."
 
You mean like "old school" mafia types? Basically a criminal but one that steals from the government, not the people, and "gives back" in a sense he builds free hospitals, gives food to hungry, keeps street criminals off people's backs.... Government then enlists them so they can use their criminal connections in other countries for intelligence work and sabotage. (see Lucky Luciano)

Not sure if you mean historical figures from past times doing this now or people from that era working in their own era.
 
Was Otto Skorzeny still bouncing around at this point? He might be a bit old, but I'm sure he'd be able. Plus, he has all sorts of useful skills.

Also, Bob Denard would probably be useful. He fought in Katanga and Algeria, and basically ran the Comoros via multiple coups between 1975 and 1995. He'd be good at general combat operations, espionage, leadership, and infiltration. He was also supported implicitly by France for most of his career, so he wouldn't offend anybody.
 
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I know he's not, like, a mass murderer or an extremely powerful figure or anything, but how about D.B. Cooper? You could just ignore all the theories about his identity and make one up. Essentially he'd be an expert at blending in and disappearing after finishing a job. Lots to work with there, I think, and he's just popular enough that people would be like "Oh, yeah! The guy who jumped out of the airplane."

How could I forget Cooper!?

Thanks! He'll probably end up being the main character that you follow (and he's way better than my original pick for that role, Charles Manson).

Okay so my cast ideas so far:

D.B. Cooper: Probably the "leader" of the group (probably a wanna-be James Bond), violent when he needs to be, stealthy when that comes in handy, can switch between the two quickly. Escape artist.

Robert "Birdman" Stroud: Still alive thanks to DARPA anti-aging technology, a Mr. Blonde type, goes from chill to crazy killer in the blink of an eye. Has trained birds with camera devices on them for surveillance. Don't fuck with his birds.

The Rosenbergs: Put on some costumes and use their ability to speak Russian and their general smarts to create diversions and steal documents. Act like a typical 1950s couple and don't get in on any of the violence unless they absolutely have to.

Che Guevara: Brainwashed by the CIA, an emotionless killing machine capable of fighting in all sorts of different environments and able to take down many men with very little.

Bruno Mussolini: Their goofy, rambling pilot. Really good at flying stealth missions.

~~ Below this line are people I'm less certain about~~

Oswald Mosley: I was thinking their communications director, calling in whatever help they need, telling Nixon what's up. Purely a desk job.

Lord Lucan: Would show up at the last minute when shit is going down and needs to be resolved quickly ala Winston Wolfe in Pulp Fiction. Last-act badass.

I need thoughts on all of these.
 
You mean like "old school" mafia types? Basically a criminal but one that steals from the government, not the people, and "gives back" in a sense he builds free hospitals, gives food to hungry, keeps street criminals off people's backs.... Government then enlists them so they can use their criminal connections in other countries for intelligence work and sabotage. (see Lucky Luciano)

Not sure if you mean historical figures from past times doing this now or people from that era working in their own era.

I mean people who were obviously criminals, but people either got sympathetic (Robert Stroud), romanticized them (D.B. Cooper), or generally stopped caring about them (The Rosenbergs).

I still need one more person to round out this team, someone who could do a brainy desk job (communications, pseudo-hacking, etc). I'd prefer this person is dead or serving a life sentence by 1973 for reasons relating to the plot.
 
Eddie Chapman, fantastic safe blower, man with incredible guts , so brave he wanted to kill hitler. Was awarded the iron cross....while working for MI6...
 
I mean people who were obviously criminals, but people either got sympathetic (Robert Stroud), romanticized them (D.B. Cooper), or generally stopped caring about them (The Rosenbergs).

I still need one more person to round out this team, someone who could do a brainy desk job (communications, pseudo-hacking, etc). I'd prefer this person is dead or serving a life sentence by 1973 for reasons relating to the plot.

Well, here's a candidate from the ranks of master-semi-villains: Spanish "financier" Juan March (1880-1962). Not a hands-on sort, and he lived and died in wealth and respectability of sorts, but very ingenious and ruthless in his way.

Or, here's someone I'm certain you've never heard of: Silas Jayne (1907-1987). He was a Chicago-area millionaire and prominent "horseman" (show horses, mainly). He was also apparently a terrifying psychotic, with all sorts of bizarre things going on around him that every one was afraid to talk about, even when they didn't directly involve him - until he was safely dead.
 
A lot of mercenaries are running around at this time, Mike Hoare, the mentioned Bob Denard, Kongo-Müller and Rolf Steiner for example.

Also, though not a bad guy Erich Hartmann left the Luftwaffe in 1970 and may be available as pilot.
 
Okay so my cast ideas so far:

D.B. Cooper: Probably the "leader" of the group (probably a wanna-be James Bond), violent when he needs to be, stealthy when that comes in handy, can switch between the two quickly. Escape artist.

...

Zacoftheaxes, I love this concept, and it's particularly amusing if you imagine your cast roster as read by the announcer from the Superfriends.
 
Zacoftheaxes, I love this concept, and it's particularly amusing if you imagine your cast roster as read by the announcer from the Superfriends.

The entire concept (from a dream) was using historical figures to make some sort of dark comedy version of superhero teams like The Avengers, The Justice League, and Suicide Squad, so that's exactly what I was going for. :D
 
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