"Of course he can get out of there whenever he wishes. He can even be declared innocent if he wanted. But he doesn't do that, because he has no need to leave the building."Sometimes the Big Bad is such a Manipulative Bastard that throwing him into prison isn't much of a hindrance to him. It's not necessarily that he's in a Cardboard Prison and can get out at any time, or that he's in a Luxury Prison Suite and thus might not even notice his circumstances. Rather, it's that while he's in prison, he is still capable of leading his organization and moving his schemes against the good guys forward. Prison is just a change of location for him, and won't slow down his evil plot to take over the world for one nanosecond. Even better, he's now in a secure location protected by high walls and armed men, and surrounded by fellow criminals who are easily manipulated thanks to their own lack of opportunities. It's like a made-to-order Supervillain Lair provided by the taxpayer! In fact, the greatest of chessmasters actually plan for their eventual imprisonment and make getting caught a part of their overall Evil Plan from the beginning. This way they benefit regardless of their plan's success or failure. Often combines with a Luxury Prison Suite in the worst cases. Compare Leaking Can of Evil for similar effects with supernatural evils.
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Anime & Manga
- Polpo, the high-ranking mafia operative from JoJo's Bizarre Adventure, stays in his cell partly because he can still give orders to his men and he can get anything he wants in prison, but mainly because he's so massive that getting him out would be a pain.
- In Zettai Karen Children, Kyosuke is the world's most powerful psychic. He is kept in a cell that is supposed to block all psychic powers. He has no difficulty leading his esper organization PANDRA from there (even going as far as having some of the members in the same cell without anyone knowing).
- In Gunsmith Cats, Gray is able to keep control of his gang and even orchestrate his own escape from inside prison.
- In the Green Lantern comics, powerfully telepathic arch-villain Hector Hammond's body is imprisoned (he's serving multiple life sentences) and is supposedly under the effects of a psionic inhibitor... but Hammond's mind is so powerful that he can still telepathically control people hundreds or even thousands of miles away from the prison without ever leaving his cell.
- Pre-Crisis on Infinite Earths Lex Luthor regularly ran his criminal enterprises from the inside of his prison cell. Of course, it was basically understood, if not ever explicitly admitted, that Luthor was in prison only as long as Luthor wanted to be in prison. Post-Crisis, that is still true, but this time he'll usually just wait for his lawyers to get him out instead.
- The Kingpin zig-zags this trope. On the one hand, he is still fully capable of running a criminal enterprise from inside prison and once even tricked Iron Man into eliminating a competitor on the outside for him, able to do so because he still had enough information on the wider criminal underworld to make deals and manipulate the authorities. In a one-shot an ex-con who had been in prison for years remarks that the Kingpin is still the number 1 crime boss in the city after all that time, despite Fisk being behind bars at that point. On the other hand, he's only in prison after Daredevil managed to bring down most of his old criminal empire so what he had was just a shadow of his former glory, and while in prison he had made enough enemies that a lot of guys — even some of his own men — made repeated attempts to kill him. It's blatantly clear from his numerous failed deals and escape attempts that he didn't want to be in prison, and Daredevil as well as the Feds took twisted pleasure in making sure he stayed there every time he thought he was about to get out. Eventually, he only does because his wife convinces Matt to be his lawyer and gets all charges dropped.
- An unusual version in the Marvel Universe: The Mad Thinker spent several years of real time in an ordinary prison cell—but his brain implant enabled him to project his mind into android duplicates, enabling him to enjoy life and go on the occasional crime spree.
- Foe Warren White, aka the Great White Shark, runs a profitable criminal empire (mostly catering to fellow members of Batman's Rogues Gallery) from inside Arkham Asylum. White was originally just a white-collar criminal who very stupidly used the Insanity Defense to avoid going to prison for committing the biggest fraud in U.S history — the judge chose to send him to Arkham, which was a hundred times worse. White only became a psychotic crime boss after he was sent to Arkham and endured all the abuse and trauma and mutilation that came with it (with half the staff turning blind eye since White's crime touched them too) — he didn't even have a criminal empire before he went in!
- The Ratcatcher can control the massive amount of rats in Gotham from inside of his prison cell.
- In The '70s, when The Joker had his own bimonthly comic book, the writers had a conundrum. On one hand, the Comics Code Authority at the time required that villains never get away at the end of a story, to show that Justice Will Prevail. On the other hand, showing a new elaborate escape at the beginning of every issue would get tedious and take precious pages away from the story they wanted to tell. Their solution? Give the Joker an Elaborate Underground Base located directly beneath Arkham Asylum, called the "Ha-Hacienda". He even had a Secret Underground Passage in his cell. Apparently, nobody at the CCA tripped to the Fridge Logic of "punishing" someone by imprisoning him in a place he can walk out of at any time.
- Daredevil villain Mr. Fear at the end of the Hell to Pay storyline. In addition to the above mentioned Kingpin. Hell, most of Daredevil's higher tier villains...
- In one story during The Clone Saga, Ben Reilly suspected Carnage was loose when a red and black Symbiote started assaulting people late at night, even though Cletus Kassidy was still locked up securely in Ravencroft. This proved a certainty when Kassidy's Symbiote (without Kassidy) attacked Ben and tried to bond with him, nearly driving him to madness. As it turned out, Kassidy was sending it out of Ravencroft through the plumbing, using the sink in his cell, which was not as heavily fortified as the rest. Eventually, Ben drove it away, and it returned to Kassidy via the pipes again.
- In X-Men Noir, Warden Halloway gives the prisoners at the Welfare Island Penitentiary free rein to do whatever they want - because crime lord inmate Sean Cassidy is running a heroin trade out of the joint and bought him off with the proceeds.
- Ethan Harrow in Hard Time has the power to leave his body as an invisible force that can manipulate objects and people. He doesn't use this to commit crimes, but being able to more or less leave the prison freely at night goes a long way towards keeping him sane. He's serving 50 to life, he needs something to hold onto to keep him from losing his spirit.
- The Punisher's higher-up criminals often do this in high-security prisons (given the Crapsack World nature of the legal system here), leading to Frank occasionally getting deliberately arrested and sent to the same prison so he can do some cleaning.
- In one issue of Batgirl 2000, David Cain easily escapes from prison (where he'd been even since the conclusion of Bruce Wayne: Fugitive.) to deliver his daughter a knife as a birthday present, and then casually waltzes right back in during the middle of the investigation into how he did it.
- Mr Bridger from the original The Italian Job (1969) ran his gangland empire from his Luxury Prison Suite. To the point that when ex-con Charlie breaks back into prison to get his permission for a job, he complains to the governor about the lapse in security.
- In Law Abiding Citizen, Clyde Shelton is a grieving husband and father whose Roaring Rampage of Revenge against everyone involved in the Philadelphia criminal justice system is not even slowed by incarceration in solitary confinement. Eventually, it's revealed that he has spent the past decade digging tunnels and installing secret doors into every solitary confinement cell in the prison. Getting sent to jail and solitary was all part of his Evil Plan.
- Corsican mob leader César in Jacques Audiard's Un prophète. His gang and the prison administration obey him; he helps the protagonist, Malik, get day leave so he can run his errands for him. (Well, for most of the film anyway...)
- In American Me, la Eme gradually takes control over the drug trade on the streets of East L.A. by leveraging their control over prison into influence out in the free world. Granted, this is Truth in Television, as the real la Eme did the same thing...
- Peter Falk in Undefeated.
- An Older Than Television example, albeit an asylum variant, is The Last Will of Dr. Mabuse. Evil Genius Mabuse writes his plans for spreading chaos For the Evulz, and his entranced supervisor passes them on to the outside. So powerful is the will of Mabuse that he commits Grand Theft Me upon death to keep up the work.
- Theoretical comedy Buy & Cell is pretty much all about this. A whole prison full of convicts carry on an extensive and successful stock trading operation, as "Con Inc.", from inside the prison, even installing a whole room full of trading screens and consoles which instantly reverts to bare concrete at the touch of a button, all without the warden ever getting the slightest clue that anything out of the ordinary is happening.
- In The Apple Dumpling Gang Rides Again, the toughest guy in the prison is a robber baron named Big Mac, who pretty much rules the place, he and his gang using it as a base while continuing his crimes with a perfect alibi. Unfortunately for him, he believes Amos and Theodore's unearned reputations, and recruits them for a train robbery, getting caught in the process after the bumbling pair accidentally - as they always do - foil his plan.
- Mechanic Resurrection. Arthur Bishop's first job involves the Get into Jail Free trope, as his target is an African warlord incarcerated (along with several of his men as bodyguards) in a maximum security prison in Malaysia, on an island with shark-infested waters. He runs his arms dealing business from there, secure in the knowledge that none of his enemies can get in to kill him. Until now.
- In the massive Neal Stephenson trilogy, The Baroque Cycle, Newgate and the Tower of London can look like this: visitors freely come and go and some prisoners have a kind of parole. Humorously, high class is another kind of prison: in the Tower, you are allowed to live on the publicly accessible grounds on the entirely reasonable assumption that leaving is tantamount to admission of guilt and the forfeiture of rank, which latter is tantamount to death.
- In the Dale Brown novel Wings of Fire it eventually comes to light that Pavel Kazakov is still a real threat despite having been arrested at the end of the previous book in the series.
- In Chronicles Of Nick, Nick's father, Adarian Malachai is the ultimate evil. He was arrested for killing a multitude of people that he claimed were demons (which is later speculated to be true) and sentenced to multiple life sentences. He can break out at any point, and is virtually unbeatable to the point of guards shooting him with bullets didn't even phase him, but prefers to stay inside jail because human hate and malice power him up. of course while in jail he sets up as much as he can to get to his son.
- Averted in Soon I Will Be Invinvicle, where Doctor Impossible notes the great lengths they they go to to keep him from getting out or doing anything. Yet, it doesn't stop the heroes from thinking this trope is in play, such that even though he's been locked up for a year he's still the prime suspect in the disappearance of his Arch-Nemesis Core Fire.
Live Action TV
- Angelus in two episodes of Season 4 of Angel. He was stuck in a cage but was still able pit the team members against each other and manipulate his way out.
- Dumont, the recurring sociopath hacker from Jake20, could manipulate events, hack computers, and even order hits from behind bars.
- Avon Barksdale during Season 2 of The Wire. While locked up in prison, he still manages to maintain control of his business through outside correspondence with Stringer, take over the supply of drugs flowing into the prison, and spend his free time playing video games and eating KFC.
- Hogan's Heroes: The main characters are operating an underground resistance movement out of a German POW camp. They also pretty much run that prison camp in everything but the official paperwork. They also have a habit of leaving whenever they feel like it.
- In a variant on Hustle, Albert Stroller is kept hostage in a holding cell by a publicity-seeking detective, who forces his fellow con-artists to lure a bank robber into a trap. While he doesn't stay inside long enough to run a criminal empire, Albert quickly befriends the guards by (deliberately) losing poker games to them, then commits a series of crimes inside the gaol to dispose of the false evidence against his crew.
- "Genial" Harry Grout from Porridge wasn't necessarily shown to be running any business outside the prison, but he certainly was more in control of the prison itself than the governor was.
- In The Shield Antoine Mitchell taunts Vic with this fact after Vic accuses him of having Lem murdered. He didn't; Shane killed him. He says he could have, but what would be the point, since he has practically everything he had on the outside in prison and killing a cop would blow all that. He punctuates this by giving orders to a nearby prison guard, who calls him "Mr. Mitchell" in response.
- The Season 2 Story Arc of Bugs has Big Bad Jean-Daniel casually manipulating events from his prison cell to make enough money to pulling off possibly the most audacious escape plan in history: he buys the prison and lets himself out.
- Megalomaniac Dale Biderbeck is sent to prison in his first appearance in season one of Monk, but he still manages to orchestrate quite a bit of mayhem from behind bars, including an assassination attempt on the governor of California, which very nearly succeeds.
- Seemed to be the case in an episode of Psych, until the "boss" in question turned up as the next victim and it was revealed that he was never really running things at all.
- David Robert Jones of Fringe leads ZFT from prison and also orchestrates his own escape.
- In the White Collar episode "Payback", Matthew Keller arranges the kidnapping of an FBI agent from his prison cell. He then uses the proceeds of his crime to escape before he can be transferred to a more effective prison.
- On Once Upon a Time, Rumpelstiltskin is being kept in a magical prison inside a repurposed dwarven mine, but still manages to pull the strings anyway. (Admittedly, he's aided by the prison's Swiss Cheese Security, which allows the Evil Queen to just stroll up to his cell whenever she likes.) It's also later revealed that he could have walked out anytime he wanted, but he stayed because of his Xanatos Gambit.
- A Smallville episode featured people buying strategic places in Metropolis in order to buy the city's natural water supply. Winslow Schott (the Toyman) masterminded the whole operation from inside his prison cell.
- In an episode of The West Wing, some DEA agents are captured by a Colombian drug cartel, which demands that a Pablo Escobar stand-in be released from prison in exchange for their return. The Colombian government is willing to do it, leaving the White House to debate whether to give in to a terrorist demand, with Sam arguing (unsuccessfully) that because the guy has been able to order kidnappings and murders from his cell, it doesn't make any difference whether he's in prison or not.
- In an episode of Sabrina the Teenage Witch, Sabrina's Evil Twin Katrina is able to cause trouble even while behind bars, sending her a curse over the internet that turns her into a Dumb Blonde.
- Leverage: Season 4 Big Bad and former Mark Victor Dubenich, masterminds the entire eighteen episode arc from inside his prison cell, only escaping in the finale. He may not want to be in prison, but with some help from corrupt investor Jack Latimer, he doesn't let it hinder him at all.
- An episode of Bones has one man have someone murdered while in prison.
- Person of Interest: The good news is that Carl Elias has been put in prison. The bad news is that his control over organized crime has not been affected. Subverted in a later season when his enemies have regained enough power that they can arrange for a prison transfer that will result in Elias being killed 'while escaping'. Suddenly prison is no longer so safe for him.
- This also could zigzag from good to bad. As on the good side he is indebted to Team Machine and is always willing to use his underground connections to keep the various criminal organizations off their backs.
- Jimmy In And Out from Breaking Bad is a variation. Prison is nothing to him, not because of his capacity for scheming, but simply because he's been in and out of prison his whole life and is so institutionalized that it barely matters to him whether he's in prison or not. For this reason he makes money by confessing to crimes committed by people who have more to fear from a prison stretch.
- MacGyver: Jack Dalton is moving around relatively freely in his barrack in prison in "Jack in the Box", is plotting his schemes, and is eating decent food.
- Substitute "Insane Asylum" for "Prison" and you have Mona Vanderwaal's situation during the first part of Season 3 of Pretty Little Liars: Even while kept in Radley Sanitorium, she was able to freely issue instructions to the A-team and receive instructions from the leader. To hammer home just how little it matters whether or not she's in the asylum, she sneaks out during the Season 3 Halloween Episode, then promptly returns to her room at the end of it.
- Mission: Impossible: In "Reprisal", a inmate masterminds a scheme to take revenge on Jim Phelps from inside a maximum security hospital for the criminally insane.
- Doctor Who, River Song, aka Melody Pond spent her days in Stormcage Containment Facility (her nights, well, that's between her and the Doctor). She even lampshades it while returning one morning, telling the staff to shut off the alarm because, "I'm breaking in, not out!" and that she'll take breakfast "at the usual hour".
- Daredevil: Wilson Fisk is imprisoned after having having his criminal operation exposed in Season 1, but as the following season shows, he still has people working for him while he is behind bars. After Frank Castle is also imprisoned, Fisk manages to play events so that Frank kills his competition, allowing Fisk to run the entire prison. It's made clear that he is just biding his time before his inevitable release, and even gets Frank out of prison early so he can continue on his crusade against crime and get rid of any possible rivals.
- Elementary: Midway through Season 3, a cartel boss that Watson helped take down in the season premiere manages to arrange an attempted revenge hit on Watson from her prison cell. Afterwards, the cartel boss is assassinated on the order of Moriarty, who is herself still in federal custody, for daring to go after one of her Worthy Opponents.
- In the mini-series Red Fox (based on the novel by Gerald Seymour), a terrorist orders an assassination from her prison cell via a lawyer, despite their entire conversation being videotaped. As they're speaking in Trouble Entendre, no-one understands what is really being said until after attack.
- In Monopoly, a late-game tactic is to stay in jail for as long as possible. While in jail, you're still free to conduct business as usual - collecting rent from, bidding on or selling properties. Moving around the board has only two major advantages - collecting $200 for passing "Go" and having right of first refusal for landing on an unsold property. But since there are very few unsold properties in the late game and the $200 for passing "Go" is a pittance compared to landing on another player's developed property, Jail is actually the best place to be. Some players enact House Rules for this reason that rent on a jailed player's property is either free or goes towards that other popular House Rule, the "Free Parking" kitty.
- In Batman: Arkham Asylum, we learn that The Joker discovered that one of the doctors had plans to create a Venom-variant using Arkham inmates as test subjects- supported by the Ax-Crazy Knight Templar Warden-, and using a Secret Identity agreed to fund her project with his secret stash of millions of dollars. He later escapes solely to trap Batman inside while Harley Quinn stages a takeover (with the help of at least one corrupt guard), but by that point you might as well say he was running the Asylum before the events of the game even took place. And the people in charge didn't even know it.
- BioShock 2: Sofia Lamb, First-Rate Bitch that she is, not only planned her jail-sentence and the circumstances that led to it, but did so specifically because it was everything she needed when she needed it, being the perfect place for a Dark Messiah Villain with Good Publicity to expand The Rapture Family during the city's descent into madness. The fact that it wasn't a Cardboard Prison made it the perfect place for a Supervillain Lair: what's better than a tightly-guarded, easily-forgotten fortress full of potential Mooks to help her retake the city After the End?
- Infinite Space: The Krieos pirates are seemingly unaffected by the imprisonment of their leader. Turns out the warden murdered and impersonated him.
- Played with in Apollo Justice: Ace Attorney, Kristoph Gavin manages to poison two different people from behind bars, without seeing any of them for seven years... by complete coincidence, as he intended for the trap he set to kill them seven years prior. And, of course, he has Luxury Prison Suite.
- In The Elder Scrolls V: Skyrim, within Cidhna Mines, Madanach not only has a private cell with various accommodations but still holds power as the leader of the Forsworn, which Thonar Silver-Blood uses to get him to use them as his personal assassins.
- In The Elder Scrolls IV: Oblivion, the master trainer for Security, J'Baana, is currently locked up in the Imperial City's Legion compound. He still regularly participates in Thieves' Guild business, however, and a quick check of his inventory reveals that he holds the keys to every door in the compound, as well as thirty lockpicks, making the reason he even bothers to stay in the prison a mystery.
- In one episode of Justice League, Batman allowed himself to be captured by the Injustice Gang; he feigned helplessness in order to manipulate one of the Gang's members. He later revealed he could have escaped at any time, but if he did he wouldn't have had a resource "on the inside". In fact Joker was the only member Genre Savvy to flat out state they should just shoot him when they had the chance.
- The pilot episode of Darkwing Duck had its major villain, Taurus Bulba, running his operation from a prison. He could escape at anytime and he chose to remain in prison because he felt that it was the perfect hideout for him, despite constantly having to deal with an annoying warden. He even had his cell converted into an office, complete with outside phone line, and he can press a button to transform it back into a prison cell whenever the warden comes along.
- This culminates in an epic jailbreak, as he reveals he had the entire cell block he was in converted into a flying forteress, which launches, leaving behind the rest of the prison.
- In Gargoyles, David Xanatos spends a few of the early post-pilot episodes in prison for a Possession of Stolen Goods charge. It doesn't stop him from having the Manhattan Clan repeatedly attacked while he sits tight to run out his jail term for that relatively minor charge.
- As an added bonus, when he got out of prison, whenever someone brought up his criminal record, he would just respond that he paid his debt to society legally; and do they believe in the judicial/correctional system or not?
- Towards the end of the second season, Tony Dracon turns out to be just as good at running his crime syndicate from his prison cell as from his mansion. It's even implied that he could have ordered a breakout.
- In Lilo & Stitch: The Series, although the authorities think that Hamsterviel is perpetually trapped in the ceiling of his holding cell unable to do anything destructive, he's actually somehow managed to trick out the dungeon cell with various gadgets, contacts Gantu frequently, and even has objects teleported between his cell and Gantu's ship... all while the prison guards aren't looking.
- Willy Watt in Batman Beyond was fully capable of exerting his telekinetic abilities to do whatever he wanted wherever he pleased while still being in juvenile hall. Though he admits he does this on purpose because in a short time he will be let out legally and with all this power that no one is aware of. That all ends after his powers are exposed and Terry recaptures him. He's last seen shackled and wearing a Power Limiter helmet that negates his telekinesis...and he still doesn't get any visitors.
- In one episode of the western Street Fighter animated series, Bison is captured by a British team of super agents (Cammy was a former member) and sent to prison. This turned out to be a distraction on Bison's part that allowed his agents to enact a scheme that threatened all of England. Bison then forces the British government to hand over a ransom of one billion pounds sterling — all while chilling in his cell and sipping tea.
- Most of the villains of The Spectacular Spider-Man are like this. Doctor Octopus fakes a return to his old, harmless self and by pretending to have been insanenote is able to get himself into a psychiatric treatment center that's a lot less stringent than prison would be, and he starts running a criminal empire from there. Most of the other villains do their time in a maximum security Cardboard Prison and go in knowing they only have to bide their time before their underworld connections break them out. Mysterio has a robot double doing time for him, so he literally isn't in prison at all.
- in the Batman: The Animated Series episode "Dreams in Darkness", the Scarecrow is using the cave system under Arkham itself to pull off his plan, and never has to leave the actual facility at all
- In the very first episode of Young Justice the villains Captain Cold, Icicle Jr., Killer Frost and Mister Freeze are captured by different heroes and their sidekicks in separate incidents but on the same day. Batman doubts that this was a coincidence, and thought they all went down too easily, but they are all carted off to Belle Reve prison. A few episodes later, it turned out Icicle Sr., who was already in Belle Reve, arranged the whole thing and wanted them to get caught so they could help him and the other incarcerated villains stage a mass breakout, but this is foiled. Then in The Stinger, it was revealed the whole thing was an Evil Plan orchestrated by The Light to get Warden Amanda Waller fired and replaced by their man Hugo Strange, the prison psychiatrist, so that they control the prison. Over the rest of the season, various prisoners such as Mad Scientist Professor Ivo are secretly broken out of and returned to their cells, or simply asked for advice in other crimes, in order to help out the Light with their various criminal schemes, and they all seem comfortable there knowing that they secretly run the place and can leave when needed. By the penultimate episode, Batman has the proof he needs to shut the operation down, but if the matter is resolved it happens off-screen as we are never shown it. Neither Belle Reve, Strange or any of the prisoners have shown up in season 2 yet as of the mid-season summer break.
- Ben 10: Omniverse episode It Was Them has Rook mention a case where an alien criminal did this. We have yet to actually see said criminal however.
- Springfield Penitentiary doesn't exactly do a good job in holding their prisoners in The Simpsons. Look at Sideshow Bob, who easily makes parole on a regular basis.
- There are, unfortunately, a number of Real Life examples of this; mafia-dons and drug kingpins who continue to run their organization with unabated effect while behind bars, often through crooked lawyers who can pass on orders under the cover of 'Client Confidentiality', or 'bought' cops who can turn a deaf ear.
- Pablo Escobar, then Colombia's richest man, had a plea deal that meant he hired the contractors to build his own prison, "La Catedral." Rather than be a punishment, being imprisoned basically just meant he had to change his drug business' headquarters to the prison, where he was protected from his enemies and had a staff of people (that is, the guards) waiting on him hand and foot. He allegedly even used the prison to execute members of his crime syndicate who had betrayed him. There were rumors that he was seen outside this prison, visiting and shopping in local towns and cities.
- Warren Jeffs, the leader and self-proclaimed "prophet" of the FLDS Church. He's currently serving life, plus twenty years for felony child sexual assault. Unfortunately, this hasn't damaged his follower's faith in him in the slightest, and while in prison he has continued to pass edicts down to his believers through intermediaries, and written what he claims to be a new gospel, that for some reason revolves around how God would really like it if he would be allowed out of prison. Although he doesn't exactly live in luxury, a large part of sending Jeffs to prison was because it would behead the FLDS, but they just keep on going as if he was still with them.
- According to Wola (The Washington Office on South America) this is commonplace in corrupt Mexican prisons where drug cartel bosses often continue their business dealings in relative safety.
- Explicitly Defied in Italy with the 41-bis prison regime: a convict sentenced to this suffers from various communications bans intended to cut him off from contact with his former criminal associates. This was originally devised to deal with terrorists, but was later extended to Mafia members, members of child pornography/prostitution rings, kidnappers for ransom or robbery, slavers, human traffickers, gang rapists, drug traffickers and cigarette smugglers.
- To the surprise of absolutely no one familiar with him and his M.O. James "Whitey" Bulger is taking full advantage of his celebrity in prison despite being over 85 years old and in failing health. He allegedly formed an improper relationship with a female psychologist who did favors for him ala Harley Quinn and has managed to still make money off of autographed merchandise and other memorabilia that's been smuggled out.
- Prison gangs often make this trope play out in real life. Career criminals on the street have to consider what will happen if they or their friends or loved ones serve time in prison, which, given their activities and lifestyles, is very likely to eventually happen sooner or later. Prison gangs can very often become the most powerful criminal organizations outside of prison, as well as inside, by relying on this fact, and promising retaliation against people who have crossed them on the outside.
- Minimum security prisons, or "country clubs" as they are often known, are barely prisons at all. They rarely have fences, and aren't always guarded. The prisons themselves are fairly comfortable places (if not as lavish as the convicts are probably used to, more on that later.) The main incentive to stay inside them is that if a convict is caught outside them, they will have to go to a medium security prison. Given that minimum security convicts are generally white collar criminals, who would have real trouble surviving a medium security prison, this is a fairly scary thought for them.
- General Malet plotted his coup d'état of 1812 from his prison cell; the security was so relaxed that he and his accomplice Lafon managed set up a "recruiting bureau" of sorts without drawing any attention. note