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Criminal Craves Legitimacy

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"Kay, my father's way of doing things is over, it's finished. Even he knows that. I mean in five years, the Corleone Family is going to be completely legitimate. Trust me. That's all I can tell you about my business."
Michael, The Godfather

Some villains want to watch the world burn, and some want to become The City's biggest crimelord. Others, however, would much rather work the 9-5 as the mayor or quite simply spend the rest of their lives on a tropical beach drinking cocktails with little umbrellas.

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This villain knows that crime doesn't pay and that good will always triumph in the end; as a result, their plan involves propelling themselves into civilized society, or simply casting their troubles aside to retire early and count their money.

It may sound like a noble idea to not be evil anymore, but this enterprise will normally involve the death and suffering of others, and certainly implies evading justice. Hence, it generally requires a hero to step in and stop them.

Contrast with Visionary Villain, whose endgame is normally far grander. Compare with Punch-Clock Villain, since they're just a normal character trying to make some money. The inverse is Just a Gangster, who is so enamored with criminal lifestyle, he actively resists going legit. See also Tragic Villain (which may overlap in some cases).

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Examples:

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    Anime & Manga 
  • Yoshikage Kira from Jo Jos Bizarre Adventure Diamond Is Unbreakable is a normal everyday Japanese salaryman, utterly unremarkable in almost every way...except for the fact he's a serial killer with supernatural powers. Despite the incredibly destructive potential of his Stand, he has no grand plans other than to live a quiet, normal life where he's free to kill women as he pleases, and he's been able to do so in the quiet town of Morioh for decades, without the main characters knowing of his existance till the final act. Perfectly encapsulated in his Character Filibuster.
    Yoshikage Kira: "[...] I'm trying to explain that I'm a person who wishes to live a very quiet life. I take care not to trouble myself with any enemies, like winning and losing, that would cause me to lose sleep at night. That is how I deal with society, and I know that is what brings me happiness. Although, if I were to fight I wouldn't lose to anyone."

    Comic Books 
  • The Kingpin has retired or endeavoured to go legitimate on occasion, either as a way up from the underworld or under the influence of his wife Vanessa. It doesn’t tend to stick, but he finds ways to bounce back from his defeats.

    Films — Live-Action 
  • Cutthroat Island: Mad Dawg is mostly just a Bad Boss and thug for the first part, trailing after Morgan to capture the treasure. It's only later revealed that his plan is to some of the treasure to bribe governor Ainslee into a royal pardon for his crimes and then become governor of Jamaica when he leaves.
  • The Godfather: The reason why Michael went to College. Don Corleone wanted his son to be a senator or a governor. Michael's end goal is to move the business into the more legitimate territory and leave the world of crime behind. By the end of the third film, he succeeds, becoming fabulously wealthy and completely legitimate. But because of the enemies he made along the way and their efforts to strike back at him, he is also totally alone.
  • Die Hard: Hans's plan is fairly simple: make everyone think his crew are terrorists, steal 600 million dollars, fake their deaths, and then sit on a beach and earn 20% off their stolen (and believed destroyed) loot.
  • Kingsman: The Golden Circle: The villain Poppy is a powerful drug lord who's upset at not getting recognized as a savvy businesswoman with a huge profit margin. Her plot involves forcing the world to legalize drugs and allow her enterprise to become a legitimate market force.
  • The Mask of Zorro: Don Rafael Montero will use the money obtained illegally from Mexico's own land to buy California and install himself as president of a new republic.
  • The Long Good Friday: Cockney crime boss Harold Shand has been able to bankroll the transformation of the derelict London dockyards into a possible venue for a future Olympic Games, which will allow him to leave the world of crime for good.
  • Romeo Must Die: Isaak O'Day wants to parlay his illegal land grab of assorted plots the NFL wants to build a football stadium on into partial ownership of the team, granting him an entirely legal cut of a multi-billion dollar industry for the rest of his life. Too bad his second in command just wants a quick payoff.
  • The Sting: Luther wants to use his portion of the cut from the con that he and Hooker pulled at the beginning of the movie to retire from running cons and buy into a (mostly) legal business one of his relatives runs.
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    Literature 
  • In The Godfather, Michael Corleone plans to move his family to Nevada and go straight, fulfilling — at least partially — not only his own wishes, but his father's:
    Don Corleone: I never wanted this for you. I work my whole life - I don't apologize - to take care of my family, and I refused to be a fool, dancing on the string held by all those bigshots. I don't apologize - that's my life - but I thought that, that when it was your time, that you would be the one to hold the string. Senator Corleone; Governor Corleone. Well, it wasn't enough time, Michael. It wasn't enough time.
    Michael: We'll get there, pop. We'll get there.
  • In the Modesty Blaise series, part of the protagonist's backstory is that she successfully pulled this off: she had a successful criminal career, but as soon as she had amassed enough wealth to live comfortably off for the rest of her life, she retired to a life of leisure in a country that didn't have any outstanding warrants for her. The villain in The Xanadu Talisman is her Evil Counterpart, pursuing the same goal but more erratically and violently.
  • In Today We Choose Faces by Roger Zelazny, the opening premise is that the Mafia has done precisely that and is now a publicly traded company on Wall Street. The reason that the protagonist has been revived is that they need somebody from the old days to handle a job that legitimate businessmen would have no talent for and he was the only mob boss to have himself cryogenically frozen and thus be available.

    Live-Action TV 
  • Hawaii Five-0: Adam Noshimuri, son of an oyabun of the Honolulu yakuza, starts a mini-civil war in the syndicate when he tries to take their businesses legit. In a bit of Dating Catwoman, he ends up in a romance with Five-0 officer Kono Kalakaua.
  • Lucifer (2016): Lucifer meets a biker gang whose leader is tired of the criminal life, he can barely ride anymore because it's too physically taxing. He wants to use the gang's infamy to create an apparel brand.
  • Queen of the South has explored this topic a few times:
    • The series' original conflict was sparked after Don Epifanio Vargas, the longtime kingpin of Sinaloa's largest cartel, left the business to run for governor. His chosen successor Cesar was incompetent, and thus several factions began vying for control, including Vargas' wife Camila, Cesar, and Teresa Mendoza, the widow of a cartel enforcer who seemingly died when Cesar tried to purge the cartel of anyone who might challenge him.
    • In a later season, Teresa Medoza starts looking for ways to go legitimate. She contemplates investing in real estate.
  • In Snowfall, Franklin Saint promised his mother that he had a plan to leave the cocaine business. Unfortunately, he is selling crack on behalf of the CIA, so actually quitting is rather complicated.
  • The Sopranos: Carmela is in deep denial about her husband Tony's crimes, but they do give her a life of luxury. The only way she truly expresses how much she truly knows is that she's desperate for her and Tony's daughter Meadow to become a paediatrician, a highly-respected career that's nothing to do with the mob. It doesn't happen. Meadow switches majors and is well on her way to becoming an Amoral Attorney mob lawyer.
  • Vegas (2012): Vincent Savino is a mobster who in 1960 moves to Las Vegas to take over the operation of a casino for his bosses in the Chicago Outfit. He quickly realizes just how much money can be made in running a legitimate Vegas casino and decides to just go legit and reap the windfall without constant danger from law enforcement. However, his bosses are old-school mobsters with lengthy criminal records (ie unable to be legally associated with a casino in Nevada) who prefer the standard rackets like loan sharking and extortion. Savino has to put his dreams of legitimacy on hold while he tries to outmanoeuvre the other mobsters and gain the independence he needs.
  • In The Wire, Stringer Bell is using the money from his and Avon's drug business to make legitimate real estate investments, in an attempt to become wealthier than just selling drugs could make him, and get far enough away from the day to day business that he couldn't be arrested for it, which the cops call "being the bank". He ends up being killed by Omar at the end of season 3.
    • In season 2, Frank Sobotka is the head of the local stevedore union, and uses money he obtains by helping a smuggler known only as The Greek move cargo ranging from drugs to stolen cars to prostitutes to fund lobbying efforts to restore the port and bring in more legitimate business. He ends up being killed by the Greek.

    Video Games 
  • In Mafia III Big Bad Sal Marcano wishes to build a casino so that he can ditch the Mafia and go fully legitimate. That said, the way he goes about it involves illegal actions and betraying his allies, and a good part of his reasoning is considering the Civil Rights Movement to be a threat to his livelihood as a Mafia don.
  • Saints Row:
    • Benjamin King from the original Saints Row had originally been a regular gangbanger but, by the time the game opens, has managed to enter legitimate business (although still maintaining control over his old gang). This drive for legitimacy does not sit well with his younger subordinates, however, sparking off an Enemy Civil War, which the Saints exploit to bring an end to both of King's empires, criminal and legitimate alike.
    • By Saints Row: The Third, the Saints themselves face an identity crisis, with older members desiring to stay full-on gangsters, while the new generation craves legitimacy conveyed to the former gang by their takeover-slash-merger with Ultor Corporation. The game's two endings reflect this divide: one sees the Saints go fully legit by becoming national heroes, while the other has them prove their cred in the criminal underworld.

    Western Animation 
  • Teen Titans: Jinx of the Fearsome Five starts out as a villain. In the episode that sows the seeds for her High-Heel–Face Turn, she admits that she is quite ambitious and one of the reasons she became a villain was because she wanted to be on the same level as her idol Madame Rouge. A combination of Rouge becoming a Broken Pedestal for her and her teammates' laziness and stupidity ultimately results in Jinx joining the heroes.
  • This was a running theme on Batman: The Animated Series, with several of the Dark Knight's famous Rogues Gallery trying their hand at "going straight." It rarely worked.
    • In "Harley's Holiday," Harley Quinn passes her competency hearing at Arkham Asylum and gets released. She tries her absolute best to keep from causing trouble, but a series of mishaps in a department store lead to a downward spiral. She's ultimately returned to Arkham by the episode's end, although both Batman and the doctors there believe that with a little extra time and care, she'll be OK again in the future.
    • In another episode, Poison Ivy seems to have turned over a new leaf (forgive the Incredibly Lame Pun) and, in Batman's own words, doesn't do anything more incriminating than forget to return a rented video on time. Ivy actually does want to have a crime-free life, but her plant-based biology has left her infertile, so she instead attempts to generate plant-based lifeforms to be her "family," which Batman can't abide when said lifeforms engage in kidnapping and murder.
    • One episode sees The Riddler apparently going straight and using his genius intellect to design puzzles and games to earn a fortune honestly. Unlike most examples on this list, it's subverted, as Riddler isn't really interested in his work—he's just pretending to gain public favor. He thus continues his crime sprees, deliberately taunting the Dark Knight with clues to his latest robberies in his sales pitches.
    • The final season of the show, retitled The New Adventures of Batman and Robin, had this as a rule with The Penguin. In addition to an overall redesign that made him appear far more human, Penguin insists that he is a "legitimate businessman" and runs the Iceberg Lounge as an posh nightclub. It's downplayed in that he's still involved in some shady dealings, but he has genuinely given up committing crimes himself.
      • An earlier episode, "Birds of a Feather," garners Penguin some genuine sympathy. Veronica Vreeland, a catty society woman, and her equally-wealthy and unscrupulous friend Pierce decide to have Veronica pretend to be interested in the Penguin as a prank. He's stunned by her affections (at this point, he was a serious Gonk) and tries to clean up his act to impress her, even bravely defending her from thugs. When Veronica realizes that Penguin is legitimately trying to be kind to her, she has second thoughts, but Pierce insists on pushing the joke despite a warning from Batman that Evil Is Not a Toy. Ultimately, Penguin discovers the ruse and, heartbroken, decides to be just as evil as Veronica and Pierce thought he was.
    • This trope is used for a Twist Ending in "Judgment Day," a New Adventures episode. A mysterious new villain known only as "The Judge" appears in Gotham and starts doling out vigilante justice to super-criminals. One of his targets is Two-Face, prompting Batman to an attempt an Enemy Mine situation, which the former D.A. rejects. The end, though, reveals that the Judge actually is Two-Face—or, more specifically, a third personality that wants Harvey Dent to return to his legal roots and dole out punishments again. The dissociative split is so great that Two-Face himself has no idea that he is the Judge, and the episode ends with the two personalities clashing in a cell in Arkham.

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