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Unions Suck

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Thanks to the fact that most aspects of major American narrative entertainment features ("movies") and series ("TV shows") are unionized, creators tend to be very familiar with the inner workings of unions, especially since they provide many benefits on their behalf such as dental plans.
However, in many works of fiction, workers' unions are not portrayed in a wholly positive light. In many of these instances, the unions and their leadership are often portrayed as corrupt, obstructive, incompetent, criminal, or even a combination of these traits. Generally, this trope comes in two flavors:
Useless unions are likely to be full of Obstructive Bureaucrats, have weird rules that get in the way of accomplishing anything, go on strikes for ridiculous reasons (especially if a Weird Trade Union), or get in the way of firing members who are in the Wrong Line of Work.
Corrupt unions are likely to require bribes to get work done, give bribes to officials to be given work, practice Nepotism, and extort their own members if filled with particularly Bad Bosses.
They are often also tied to or owned by one of the many types of criminal organizations (most notably The Mafia), and if so may serve either as a front or a money laundering tool, and are likely to be used for smuggling if they have anything to do with transportation. Police unions in particular are often portrayed in left-leaning media as covering for dirty, bigoted, rabid, and/or killer cops. They may also be portrayed as Category Traitors to organized labor as a whole for harassing workers trying to organize other workplaces.
This trope is not to be confused with Weird Trade Union, which revolves around labor unions for the unlikeliest of professions. Contrast Strike Episode, which usually depicts a benign union.
No Real Life Examples, Please!!

Examples
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Played with in the "Dead-End Kids" arc of Runaways, in which the Runaways are sent back in time to the 1900s and Victor gets involved in a labor strike. On the one hand, the unions have criminal ties and aren't afraid to throw punches, but on the other hand, the cops and the industrialists are far worse, with the cops being xenophobes who enjoy beating up immigrants and the industrialists allowing their own workers to die in unsafe conditions to save money.
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The Simpsons:
The episode "Last Exit to Springfield" provides the page quote. Mr. Burns has become fed up with the various stipulations in the plant's union contract (the workers are guaranteed a green cookie on Saint Patrick's Day) and decides to revoke their dental plan. It's also implied that the previous union president was murdered for trying to clean up the corruption in it.
In "Maximum Homerdrive" it's revealed mid-way through that the truckers' union is running a scam where they've secretly installed "auto-drives" in all the trucks. Whilst it was originally designed to take over in an emergency when the driver was incapacitated, all the truckers have gotten lazy and are using the auto-drives to do all the work, whilst still receiving their full payment for the jobs. When Homer and Bart's antics nearly expose the scam, the truckers flat-out try to murder them. In the end, after witnessing Homer do an impossible stunt, one of them is inspired to go back to doing the actual work themselves, only for the others to dismiss the suggestion and move on to a new scam.
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Anna's Quest: One of prison guards complains about a union which is "practically non-existent" because meetings are always postponed to another time
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In On the Waterfront, the stevedores' union is controlled by mob boss Johnny Friendly, who uses it to extort workers to line his own pockets and silences or kills anyone who tries to stop him.
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Dilbert: In one Sunday strip, Dogbert forms a union that he says will help Dilbert and his coworkers. However, the last panel has him saying they should talk about union dues, implying he actually started it for his own benefit.
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Animaniacs: The Warner siblings arrive at Beethoven's house to sweep his chimney, only to immediately go on a lunch break before starting any work. When Beethoven questions why they're taking a break before doing anything, Dot smugly informs him they're unionized.
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Regalia: Of Men and Monarchs: The Unity is, ostensibly, a union of peasants in the kingdom of Ascalia. In practice, their leader is an Entitled Bitch who forces protagonists to solve assorted problems of her men, many of which were created by them in the first place. The rest of the Unity are a bunch of Medieval Morons, who don't even know what they want half the time but are ready to get Torches and Pitchforks up at a moment's notice.
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Brooklyn Nine-Nine's final season sees the cast square off against the police union, which is depicted as a corrupt organization that covers up the crimes of its officers.
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Played both ways in Blue Bloods depending on the episode.
Frank Reagan, the police commissioner, frequently clashes with the NYPD's union. In the second episode, he heads off "blue flu" threat by the head of the NYPD union by bringing a large number of line officers into the contract negotiations, and wryly noting not one of them has the sniffles. Several seasons later he nearly faces a no-confidence vote from the union for apologizing that an officer accidentally killed an innocent man.
On the other hand, a later episode has Detective Danny Reagan being sympathetic to a labor strike at a construction site sparked by a deadly accident:
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The John Larroquette Show, John learns fairly early after arriving to manage the bus depot that getting Gene to do any actual work is near impossible, because he's a Union employee.
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"Captain Sturdy: Back in Action" is about an Old Superhero forced to come out of retirement because the superhero union raised the retirement age. The union is too busy building expensive new facilities to properly train their superheroes, making them lackluster crimefighters.
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Alluded to in Fallout 4: During the quest "Unlikely Valentine", the player eavesdrops on a conversation between 2 members of the Triggermen gang. One wonders why there's a vault beneath a subway station when it wouldn't be airtight, defeating the whole point, and his friend tells him that a common scam in Pre-War America was to get a load of union boys to run a construction job that wasn't intended to go anywhere but still keep everyone on payroll.
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Storm Hawks: In "The Last Stand", the Storm Hawks are stranded in the Wastelands with a bunch of unionized Wallop miners and are besieged by Mr. Moss with an army of fire scorpions. They work together to hold off the army, but the miners periodically stop working to take their scheduled breaks, even in the middle of being bombarded. They are also rudely dismissive of Junko, who idolizes them.
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Adrian Mole: In Wilderness Years, Adrian asks a potential employer if she objects to him belonging to a union. She says she does, saying that the greatest achievement of Margaret Thatcher was to tame the unions.
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Raising the Wind: While the students are moving into their new digs, they have to wait for the removal men to finish their tea break, which Mervyn points out in an acidic tone is union rules.
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In The Flintstones, Fred and Barney need to have a house moved, but the workers they contracted spend most of their time on union-mandated breaks, forcing them to do it themselves.
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Nursery Crime has the Guild of Detectives, who care more about whether a crime being solved makes for a good story vs. whether or not the culprit was actually caught; detectives who can make their stories more literary, such as Friedland Chymes or Hercule Porridge enjoy fame and success, while Jack Spratt, the protagonist of the novel, can't even get the press to listen to his statements about how the prosecution in a murder case fell apart.
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In Carry On at Your Convenience, the union representative at the plumbing factory calls strikes on flimsy pretexts whenever he fancies attending a football match.
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This was a recurring joke on Not the Nine O'Clock News; sketches included a shop steward filing a complaint about a dead employee's "unfair dismissal", and a group at a TUC conference using their proxy votes to determine whether tea or coffee was going to be served during a break.
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Grosse Pointe Blank combines this with Weird Trade Union, as they are assassins. It is definitely on the corrupt side of the trope, with all union actions being targeted at either forcing membership (and thus sucking up part of members pay for their contracts) or simply killing any non-unionised assassins. It's all Played for Laughs.
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RiffTrax: In the riff on the commercials that aired during The Star Wars Holiday Special, they joke that a union means "kickbacks and secret ballots and bodies buried in end zones".
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Futurama: In "Bendless Love", it's revealed the factory of Bending Robots strike is supported by the Robot Mafia, who are even the "duly elected" mobsters of the union. They likewise try to kill Flexo for being a scab, though granted this is cause Donbot is enraged at the idea of money being paid out to workers without him getting a cut.
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The Venture Bros.:
Throughout the series, the Guild of Calamitous Intent is a Weird Trade Union for supervillains. As one might expect from a villainous union, they are not depicted in a flattering light. There's corruption (Guild members taking bribes to bend its rules, falsifying the details of a "protagonist" death in order to live off of "arching insurance"), power struggles (the current Sovereign got the position by performing a Klingon Promotion, then Phantom Limb tries to pull The Starscream on him), an ossified and hidebound power structure (the Council of 13 hasn't added a new member in decades, meaning they're all old and out of touch), and loads of bureaucratic red tape that chafes the villains, especially the Monarch, preventing them from "arching" who they want.
In "The Doctor is Sin", Dr. Venture reveals that the "Super-Science" Laborers Union has been on strike for years, further crippling the already nearly bankrupt Venture Industries who wouldn't be able to meet their demands anyway. A union forcing its members out of work for so long with no hope of actually accomplishing anything qualifies as "sucking". Dr. Killinger murders their leaders and hires a bunch of prisoners as scabs as part of a "work release" program, getting Venture Industries back up and running as part of his plan to convert Dr. Venture into a supervillain.
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Discussed in Microserfs:
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Robot Chicken: One skit parodying Bob the Builder has Bob and friends kill a group of union thugs who try to stop him from doing some scab work.
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Disco Elysium's Crapsack World skewers all forms of organizations and ideologies, with unions being no exception. The Debardeurs' Union that controls Martinaise is basically just a Neighbourhood Friendly Gang, led by the corrupt Evrart, and sustained by an illegal drug trade. Their saving grace is that they have imposed some form of order and law in the deteriorating town and the corporation they oppose is also corrupt and morally bankrupt. It's eventually revealed that while Evrart does genuinely believe in socialist ideals, he still wants to be the one in charge when the revolution happens once again.
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In The Wire's second season, the stevedore's union is corrupt, helping smugglers move their products in exchange for money that their boss Frank Sobotka is using to try and bribe officials to expand the docks, allowing them to bring in more legitimate work.
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In Unbreakable Kimmy Schmidt, many jokes are made at the expense of construction unions, such as that Mikey's union gives everyone the day off whenever anyone on a crew has a birthday, and that some people are hired as "hole watchers" who stand around watching other people dig.
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The Valley of Fear portrays a coal miners' union as a front for a Secret Society called the Scowrers, who were in cahoots with organized crime.
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The Sopranos: The DiMeo crime family has long worked their way into various labor unions, particularly construction, that they exploit for personal gain, such as "no show" jobs for crew members where they receive full salaries and benefits without ever needing to do actual work.
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Cobra Kai: After the big school brawl in the Season 2 finale, the West Valley High School parents are furious that the school staff members not only let the incident happen but that they've avoided any consequences for it. The school counselor explains that they were following the NEA's guidelines on student fights.
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