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Just a Gangster

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There are many stories where a criminal dreams of leaving the life of the criminal behind them, either seeking to turn their organization into a legitimate business empire or to retire.
This is not that type of character.
A character who is Just a Gangster is someone who either passes up or actively resists opportunities to reform. The reasons for this may vary: some may feel that going legit is dreaming too big and trying to reach unattainable goals, others do it because being a gangster is the only thing he was ever good at and he recognizes that he'll just be out of place in the legit world, or because they believe wholeheartedly in Damn, It Feels Good to Be a Gangster! and Evil Feels Good.
In many cases, if a criminal kingpin or high ranking member of organized crime is trying to leave the criminal underworld and take their organization with them, a Just A Gangster character may work to undermine and sabotage the attempt. After all, if a crime gang goes legit, it's the ones with the cleanest hands such as the guys who run the numbers and "earn well" who will blend in better than the foot-soldiers who do the dirty work. As such those foot soldiers or members who are only skilled in violence or traditional crime may fear becoming a "liability" when this regime change happens, in a way that workers may feel about outsourcing or the Job-Stealing Robot. It can also lead to an irony in that the legit character only manages to make the transition by doing One Last Job, purging his former gang and then walking to a legal line of work, or at least one with legal protection.
Expect the character who is Just A Gangster to accuse the legit character of "having become a sell-out" or "becoming soft" during their Motive Rant, oftentimes much to their peril.
Compare and contrast Resignations Not Accepted, No Place for Me There, Satisfied Street Rat, Chronic Villainy, and Visionary Villain. If someone wants to leave a life of crime but cannot because they'll be killed if they do, that's Trapped in Villainy. Underlings who try to undermine a boss from retiring or making the organization legitimate often overlap with The Starscream and Dragon with an Agenda. Often leads to A House Divided.

Examples
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DBTropes
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In The Long Good Friday, the London Gangster Harold Shand strives to become a respectable and legitimate businessman through land speculation aided by some American mob contacts. This goal is undermined when his project starts being attacked and his men killed. Harold thinks he's experiencing a case of this- suspecting treason from his men and believing The Irish Mob is attempting to muscle in. However, he's actually being targeted by the IRA during The Troubles.
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Lex Luthor is the biggest offender. He was originally a diabolical mastermind and Mad Scientist whose inventions begged the question why he would try and kill Superman or rob banks. In the Post-Crisis continuity, Luthor became a Corrupt Corporate Executive and tech-magnate, yet he still devoted time, money and resources to killing Superman, the Justice League and other endeavours. He even became US President, and held a Mask of Sanity for a while before he tried to kill Superman again. Luthor insisted that without Superman he would be the great hero and "cure cancer." Yet during 52, when Superman was missing for a year, Luthor once again lapsed into villainy and on his return, Superman asked "Where's the cure for cancer, Lex?"
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Norman Osborn, Luthor's Marvel Counterpart is another big handler. He was a businessman who became a supervillain and aspiring crimelord, before returning to become a businessman and politician. He then lapsed into insanity, started a Mystery Cult dedicated to being a Goblin and returned to full-time villainy again.
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Grand Theft Auto V has Michael who is an ex-heister bored by Stepford Suburbia, while Franklin is a ghetto hood who, like CJ, wants to move up the crime ladder and work for bigger scores. Trevor however is entirely conformtable being a criminal and wouldn't dream of being anything else.
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In Narcos, Gustavo criticizes Pablo for his lofty political ambitions, which have caused a lot of trouble for the cartel, and tells him that he needs to remember that they're just criminals. Pablo's fury with the Colombian elites for rejecting him escalates into a full-out war against the government.
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Hawaii Five-0: Adam Noshimuri takes over for his father as the head of the Yakuza in Hawaii, then decides he wants to take all of the Yakuza's Hawaiian business interests legitimate. When Adam's brother gets out of prison, Adam plans to set his brother up with a cushy business position, but his brother, hardened by his time on the inside, is more interested in colluding with other Hawaiian Yakuza members who aren't happy with the prospect of going straight. It ends about as well as you'd expect.
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Unusual example in The Superior Foes of Spider-Man. The gangster Tombstone loves his daughter, Janice, and has invested in her education including law school (in which she has excelled) in part because he wants her to become an Amoral Attorney providing his organization with a legitimate front. Tombstone sees that as essentially legalized crime, where Janice would get all the benefits of being a gangster without any of the drawbacks. However, Janice would rather be a supervillain acting in the open - not because she's violent or crazy, but essentially because she wants to break the glass ceiling of the criminal underworld and sees being The Woman Behind The Man as counterproductive.
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Prequel series Better Call Saul demonstrates that Saul himself has shades of this. Jimmy McGill (Saul's real name) had ample opportunities to be a legitimate lawyer or businessman, and would probably have been very successful due to his talents, charisma, and intelligence. However, the irresistible thrill of being a conman and crooked lawyer meant he couldn't be happy working on the right side of the law. (Having his career progress secretly undermined by his brother during a period when Jimmy was genuinely trying to be legit didn't help either.) He’s also simply unable to understand basic work ethics like waiting for the bosses' approval to run his commercial or not fabricating evidence which ruins his attempts at legitimate business practices.
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Saints Row:
Ben King in the first game managed to raise his street gang, the Vice Kings, to a state of semi-legitimacy, focusing more on the operation of his legal (but still rather corrupt) record label than his illegal prostitution and gambling rings and using his connections to city councilors, judges and the chief of police to keep the Vice Kings out of the spotlight. His lieutenant Warren Williams, on the other hand, feels that schmoozing politicians is a waste of time and demands they start an all-out gang war with the 3rd Street Saints whenever they're brought up. It's for these reasons that he feels that King's gone soft and tries to take over late in the VK story arc. What's interesting is that Warren is King's "numbers guy" and the front manager of his record label, and would be in the best position to profit from a turn to legitimacy, but because he's young, brash and feels that he's got something to prove, he can't see that.
Likewise, Saints member Johnny Gat prefers the random mayhem and heists to the multimedia franchise (complete with Saints Flow energy drink) the gang has become by Saints Row: The Third, and accuses them of "trading in our dicks for pussies." This is why The Boss is the one in charge even though Gat has seniority, because Gat is too Hot-Blooded to even do the simplest non-violent parts of being a gangster and the Boss is too much of a friend for Gat to outright defy.
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Top Boy constantly emphasises how each of it’s main protagonists feel like this, Dushane and Sully have been striving to be on the Roads since they were kids and realise that essentially this is all they really have in life.
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In Cowboy Bebop the Red Dragon Syndicate was less trying to become legitimate and more becoming Neighborhood-Friendly Gangsters. Vicious, the most powerful assassin/enforcer for the Red Dragons and a supreme Blood Knight psycho, however, sabotages these efforts first by assassinating both Red Dragon capo Mao Yenrai and a captain from a rival syndicate who were looking to make peace, and later performs a coup against the highest echelons of the Red Dragons leadership, making himself the kingpin of the syndicate and presumably looking to start bloody wars against his various enemies.
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Uncle Enzo has to grapple with the implications of the trope in Snow Crash. With the breakdown of government, Uncle Enzo has successfully transformed The Mafia into a vast diversified company. They still do loan sharking and theft as necessary, but their most profitable division is the Nova Sicilia chain of pizzerias (Pizza delivered in 30 minutes or its free. And the delivery drivers really don't want to disappoint their Mafia superiors, so it's always on time). Unfortunately this means that most of their members are just normal rank-and-file corporate workers and not gangsters anymore. Uncle Enzo sees very little worthwhile material in the Young Mafia, and fears that once he and his lieutenants die of old age the Mafia will turn into just another interchangeable corporate entity.
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Assassin's Creed IV: Black Flag deals with pirates rather than gangsters and is set in the Carribean during The Golden Age of Piracy. Most of the pirates are former Privateers and honest sailors who eventually went rogue because of poor pay and terrible conditions. They set up a Pirate Republic in Nassau, with Benjamin Hornigold hoping that this experiment in democracy will eventually lead them to give up on their criminal origins. As time goes on however it becomes obvious that this is just a pipe dream:
Benjamin Hornigold decides to take the King's pardon and becomes a pirate hunter. Blackbeard stages a series of robberies to get medicines for Nassau but decides finally that he'll take the pardon and retire. Problem is that his reputation is serious enough that he faces Retirony and is attacked at a party. Charles Vane firmly insists that he was and will remain a pirate because he was in it for the violence and ruckus, while Player Character Edward Kenway wants the elusive fortune, a big score that will allow him to retire.
The game's Big Bad, Bartholomew Roberts has a more nihilistic take on this trope. He starts out as an honest sailor, but being repeatedly chased by multiple targets ultimately leads him to becoming a pirate. Upon taking a pirate, he spouts a creed of "A merry life but a short one, the world owes us nothing more". He embraces the violence and daring pirate life knowing fully well that he'll die, but damn it if he isn't going to have fun while he's still kicking.
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Grand Theft Auto has a running conflict between gangsters who broaden their horizons and go into other areas, and those who want to stick to what they're good at:
Grand Theft Auto: Vice City has Tommy Vercetti who was a mob hitman who wants to make a transition into legitimate business, while his mob bosses back in Liberty City wanted him to remain as a gangster. Lance Vance is likewise not as competent in civilian endeavors, so they turn on Tommy and he ends up killing them all.
Grand Theft Auto: San Andreas has this conflict in the hood. CJ sees no hope in the old community-oriented gang represented by his elder brother Sweet, because they don't make enough money and can't compete with the drug dealing Ballas gangs. His friends, Big Smoke and Ryder, also agree but where they betray Sweet and CJ and go into the drug business, CJ works as a freelance mercenary doing jobs for the Triads, the US Government, and eventually becoming a legitimate entertainment mogul, though at Sweet's stubborn insistence, he returns to his gangster ways to reclaim the hood.
Grand Theft Auto IV and its two expansion pack also explores it. Niko Bellic laments that it's unlikely he'll ever be anything more than a hitman and thug, since it's all he's ever known. In The Ballad of Gay Tony, Luiz actually likes being a club manager and dislikes doing gangster work even if he is good at it. The most tragic case is The Lost and the Damned; the Lost MC club are stuck in a timewarp of The '50s and are little more than thugs for other gangs. The one time Johnny Klebitz tries to fix things, he ends up destroying the club.
Grand Theft Auto V has Michael who is an ex-heister bored by Stepford Suburbia, while Franklin is a ghetto hood who, like CJ, wants to move up the crime ladder and work for bigger scores. Trevor however is entirely conformtable being a criminal and wouldn't dream of being anything else.
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Likewise, Saints member Johnny Gat prefers the random mayhem and heists to the multimedia franchise (complete with Saints Flow energy drink) the gang has become by Saints Row: The Third, and accuses them of "trading in our dicks for pussies." This is why The Boss is the one in charge even though Gat has seniority, because Gat is too Hot-Blooded to even do the simplest non-violent parts of being a gangster and the Boss is too much of a friend for Gat to outright defy.
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Befitting her nature as a hardcore criminal, Revy from Black Lagoon hates the idea of living an honest life, as she is too violent and hot-headed to even resort to non-violent means and would rather go on killing people and committing heists instead. She is essentially a predecessor to Johnny Gat, but much more nihilistic.
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Grand Theft Auto: San Andreas has this conflict in the hood. CJ sees no hope in the old community-oriented gang represented by his elder brother Sweet, because they don't make enough money and can't compete with the drug dealing Ballas gangs. His friends, Big Smoke and Ryder, also agree but where they betray Sweet and CJ and go into the drug business, CJ works as a freelance mercenary doing jobs for the Triads, the US Government, and eventually becoming a legitimate entertainment mogul, though at Sweet's stubborn insistence, he returns to his gangster ways to reclaim the hood.
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Captain Cold from The Flash isn't content with being a small-time crook, willing to share his inventions with the world, or gung-ho enough to become a big-league supervillain. His niche is being the leader of a heist crew and he wouldn't live any other way.
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Grand Theft Auto: Vice City has Tommy Vercetti who was a mob hitman who wants to make a transition into legitimate business, while his mob bosses back in Liberty City wanted him to remain as a gangster. Lance Vance is likewise not as competent in civilian endeavors, so they turn on Tommy and he ends up killing them all.
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Ben King in the first game managed to raise his street gang, the Vice Kings, to a state of semi-legitimacy, focusing more on the operation of his legal (but still rather corrupt) record label than his illegal prostitution and gambling rings and using his connections to city councilors, judges and the chief of police to keep the Vice Kings out of the spotlight. His lieutenant Warren Williams, on the other hand, feels that schmoozing politicians is a waste of time and demands they start an all-out gang war with the 3rd Street Saints whenever they're brought up. It's for these reasons that he feels that King's gone soft and tries to take over late in the VK story arc. What's interesting is that Warren is King's "numbers guy" and the front manager of his record label, and would be in the best position to profit from a turn to legitimacy, but because he's young, brash and feels that he's got something to prove, he can't see that.
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Casino deals with this trope and shows how it happens. The mob's skimming operation in Vegas runs on a front of legitimate business and they hire Sam "Ace" Rothstein to be the man who runs things while Nicky Santoro serves as "the muscle" to protect Ace and the business. Ace is a "good earner" and a Consummate Professional, as such he improves efficiency in the casino, improves business and innovates on entertainment and by increasing the income, he increases the money the mob skims off. Nicky, being a simple and violent mob enforcer who has been given free rein by the bosses, soon goes on a series of daring heists across the city and attracts a lot of heat doing so, completely disregarding any suggestion that he should just keep things low key and focus on the mob skimming money from the casino. Eventually, the FBI gets involved and the Mob decides to clean house and leave no one alive who could testify against the bosses. "Ace" Rothstein survives because as he notes at the end, he is still a good earner and can help the mob make money through the casino, while Santoro gets brutally killed.
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Berlin Alexanderplatz describes this dynamic in twenties' Germany, via the interactions between the Mob boss Pums and his other racketeers. Since it's written by a German leftist avant-gardist, it's made into an allegory for capital-labor relations:
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In Yakuza: Like a Dragon, Daigo Dojima and Masaru Watase of the Tojo and Omi Clan respectively, have made an agreement on disbanding both Clans, in light of anti-yakuza laws being in full effect (not helped that the modern day yakuza now represent what people fear about them), and not wanting the Clans to become government pawns for their scheme. Understandably, a lot of the low-level foot soldiers are angry about this announcement and voice their displeasure by attacking them. In a rare instance, this is actually defied. Both Daigo and Masaru are aware of this trope happening, and both founded a security company so that yakuza foot soldiers will have a place in this new era and not become a liability. This also plays into Like a Dragon Gaiden: The Man Who Erased His Name, which canonically happens concurrently with the events of Like A Dragon, where the final boss is a Watase lieutenant who ends up enacting a coup because he refuses to give up the life he's built for himself as a criminal and the endgame is Kiryu helping ensure that the dissolution goes through.
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In Solo, Han repeatedly suggests Qi'ra leave Crimson Dawn and start a new life with him, but she seems reluctant, also hinting that she cannot just up and leave because of Vos. After she kills Vos, she gives Han the impression she's going to take him up on his offer... but it turns out she was lying to get him out of the way before cozying up to Maul to secure her position as Vos's replacement.
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In Romeo Must Die, Isaak plans to move his criminal empire into the legit world by becoming the owner of a new sports team, but The Dragon, Mac, rejects this, saying that all he ever wanted was control of the street. He also reveals that he's been covertly working against Isaak's dream throughout the whole movie and trying to inflame a Mob War against their Chinese rivals.
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The Wire is the Trope Namer.
The top figures in the Barksdale drug empire are Avon Barksdale and his friend since childhood, Russel "Stringer" Bell. At the end of Season 1 Avon is arrested on possession charges and goes to jail, leaving Stringer as the acting head of the group. During that time Stringer, who has always been the more intellectual of the two and more interested in the legit world, comes to realize that the Barksdales cannot survive by continuing Avon's style of constant warring with other gangs and attempting to seize control of the streets, so he makes peace with the various rivals of the Barksdale group and pushes the gang both towards legitimate investments and becoming the supplier for drugs to all the gangs in the city, rather than just another gang peddling drugs on the corners. By the time Avon gets out of prison Stringer seems tantalizingly close to the legitimate business world he's been dreaming of, but Avon is dead set on still being an old school gangster and has no use for Stringer's ambitions. That disagreement, combined with a powerful new gang that challenges the Barksdales to a Mob War, results in Stringer getting killed, Avon going back to jail, and the Barksdale empire collapsing entirely.
Their successor Marlo Stanfield, when he and his gang are finally indicted, is given a deal by the DA to walk away from the criminal life a rich man because of political necessities and the fact that two rogue cops misappropriated police funds to put illegal wiretaps on Marlo. After retiring he's introduced to various businessmen by drug lawyer Maurice Levy, but Marlo slips away from the party to go back and fight with some corner boys because that's all he really knows and what he does best. Marlo is obsessed with the drug trade and his street reputation, far too much to ever leave it behind. Although his final fate is left open-ended, it's clear that this will inevitably end with him either in jail or as another corpse on the streets.
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In an episode of Lois & Clark a crime boss steps down and his two offspring, a son and a daughter, end up having a turf war over how to run the family business. The son basically wants to continue conducting business as usual while the daughter, who went to business school, realizes that the enterprise could make a lot more money if they went legit while adding some even more profitable illegal activities on the side. But nobody pays attention to her suggestions because she's just a woman.
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Grand Theft Auto IV and its two expansion pack also explores it. Niko Bellic laments that it's unlikely he'll ever be anything more than a hitman and thug, since it's all he's ever known. In The Ballad of Gay Tony, Luiz actually likes being a club manager and dislikes doing gangster work even if he is good at it. The most tragic case is The Lost and the Damned; the Lost MC club are stuck in a timewarp of The '50s and are little more than thugs for other gangs. The one time Johnny Klebitz tries to fix things, he ends up destroying the club.
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The Departed has Frank Costello (Jack Nicholson) who can't think beyond being a 30s Gangster, and living and acting like one, in the 21st Century. He and his outfit survive as long as they do only because Costello is a stooge for the FBI, who use him as a way to crack down on other, more dangerous gangs like the Chinese, who are involved in bigger schemes. Sullivan, (Costello's mole within the police department) on the other hand, is a cold Social Climber who wants to study law and become a politician to advance in society. Costello sneers at Sullivan's ambition, and in the end Sullivan wipes out Costello and his whole gang to move ahead.
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Breaking Bad has both Walt and Jesse show variations of this;
Walt gets all the money his family could possibly need by the middle of the series, but keeps on cooking meth because of his overwhelming ego, and when asked directly what exactly he's trying to achieve by continuing to cook, he replies with his famous "I'm in the empire business" speech and willingly embraces his status as The Dreaded Heisenberg.
Jesse actually tries to quit the business several times, but tends to sink into depression and apathy when he doesn't have drugs (either making them or taking them) to distract him from the guilt of all the things he's done. Jesse also has a memorable scene where his Amoral Attorney is presenting him with various tax dodges and money-laundering methods to stop the police from getting suspicious, only for Jesse to adamantly refuse, because what's the point of being a criminal if you're going to have to do the same annoying legal stuff you'd have to if you were an honest businessman?
Prequel series Better Call Saul demonstrates that Saul himself has shades of this. Jimmy McGill (Saul's real name) had ample opportunities to be a legitimate lawyer or businessman, and would probably have been very successful due to his talents, charisma, and intelligence. However, the irresistible thrill of being a conman and crooked lawyer meant he couldn't be happy working on the right side of the law. (Having his career progress secretly undermined by his brother during a period when Jimmy was genuinely trying to be legit didn't help either.) He’s also simply unable to understand basic work ethics like waiting for the bosses' approval to run his commercial or not fabricating evidence which ruins his attempts at legitimate business practices.
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During an early episode of Burn Notice, Michael is hired to save a local neighborhood from Concha, a cruel gangster who is demanding outrageous amounts of protection money from residents. Eventually it's revealed that Concha is deliberately setting the prices too high to afford, because she has a scheme to drive residents out, buy up the vacated properties through seemingly unrelated businesses, and then make millions when the area is targeted for urban redevelopment. Her older and more traditional dragon Diego disapproves of the scheme and Concha's callous readiness to kill anyone who gets in her way. (Including their entire family too.) Michael cuts a deal with Diego to help get rid of Concha if Diego and the rest of the gang leave the neighborhood and find someplace else to run their rackets. Diego agrees, helps get rid of Concha and goes about being a gangster offscreen instead of taking advantage of her plan to make "legit" money.
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Coyote Ragtime Show revolves around the race to reach Planet Graceland, where the loot of a super-heist that stole all of the money from the bank that funds all of the colonized solar systems is hidden. About halfway through The Hero "Mister" tells Franca, the Tagalong Kid, the story of how her father Bruce pulled off that heist: by becoming a bank executive and climbing all the way to CEO so he could get the necessary access codes, revolutionizing every part of the bank's procedures he was involved with. Mister admits that becoming CEO would have given him an insane amount of money to settle with his daughter in peace somewhere in a lawful fashion, but then he muses that Bruce probably wanted the rep of pulling it off much more.
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The following is a list of statements referring to the current page from other pages.

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