Boxed Crook

""If you accept, your sentence will be reduced after we drive off the hobgoblin horde. Or, you can refuse and pray their catapults don't hit the prison tower while you're still locked inside.""

- Hinjo, The Order of the Stick #420

A prisoner or group of prisoners facing either execution or an extended stay at the Greybar Hilton (being guilty of the crime is optional) is approached by a mysterious figure and offered their freedom, provided they do the government a little favor first. The prisoner is very often a highly trained special operator with above average skills who went wrong somewhere. If a group, prone to being a Ragtag Bunch of Misfits who cannot rely on each other; their crimes will vary (and quite possibly their guilt as well).

The mission the prisoner is required to undertake will, of course, have a very low probability of survival. It will also require a high degree of plausible deniability on the part of the government should things go sideways. Very often the government will either have no intention of keeping its end of the bargain should the prisoner succeed, or the prisoner will be locked into doing the government's off the books dirty work until they are killed or escape.

The government will usually have some form of "insurance" to make sure the prisoner actually does what the government wants, such as an Explosive Leash.

Sub-Trope of Leonine Contract.

May stem from You All Meet in a Cell. Sub-Trope of Recruiting the Criminal. Compare Condemned Contestant and Win Your Freedom.

Anime and Manga

 * Witch Hunter Robin: A hacker who broke into the Solomon mainframe is held captive in their HQ as their tech-guy. (It should be noted that this has happened in the real world).
 * The Time-Space Administration Bureau of Magical Girl Lyrical Nanoha has a track record of giving defeated opponents job offers as an alternative to prison time. Said jobs are often active-duty combat positions where said crooks may wind up facing universe-destroying Lost Logia or armies of cyborg super soldiers and the like, but many are also basically community service roles working for civilian organizations like the Saint Church. In contrast to many similar arrangements, the ex-convicts enjoy, take pride in and do well in their jobs, and their superiors, for the most part, trust them completely.
 * The manga Sukeban Deka and its anime and live action incarnations revolve around a delinquent Japanese schoolgirl fighting crime.
 * The in Blade of the Immortal are all death row criminals who are buying back their lives by collecting Itto-Ryu heads.
 * Lind L. Tailor in Death Note is set to impersonate L on a broadcast to try to see how Kira will kill him on the day of his execution. Later on, L proposes having a criminal write names in the Death Note and see if he dies 13 days later to determine whether the 13-day rule is fake, and pardoning the criminal if he or she survived,.
 * Aiber also counts, at least in the manga, where he mentions in passing that L has enough evidence on him to get him life in prison, and he likes the chance to use his con artist skills.
 * The main plot of Cyber City Oedo 808 involves taking three criminals with life sentences, putting explosive collars on them and sending them out to stop other criminals. If they succeed in their missions, they get time removed from their sentences (though all three have sentences of over 200 years, and one of them was once penalized with extra time for disobeying orders during a mission). Their goal is to eventually work off their entire prison sentence, though they hadn't come close yet by the end of the series.
 * In King of Thorn manga, the government recruit a hacker this way. The fact said hacker wants to take revenge on the infiltrated facility's system administrator certainly helps.
 * Argo Gulski in G Gundam
 * In One Piece, we have the Seven Warlords of the Sea. Seven infamous pirates given pardons by the World Government in return for their service, which is spent crushing revolutions or related regime change or dealing with other pirates. While they're often derided as "Government Dogs", many of them actually hate the World Government and all are insanely powerful, so saying that within easrhot of them is not a good idea. There's only one member who seems truly loyal to World Government and that's Bartholomew Kuma, but that's another story...
 * The prison of Impel Down is home to Shiryuu of the Rain, a former Head Gaoler whose habit of killing his charges landed him on death row in the deepest levels of the hellish prison. During a unprecedentedly massive prison riot, he's released to help control it, his sentence postponed for the duration of this second chance. Unfortunately for the staff of Impel Down, his cooperation lasts only until he regains his sword, and after that he proceeds to make things much worse by cutting through the guards and communication system before escaping with.
 * A humorous example is Curly Dadan, head of a bandit gang. Vice-Admiral Garp is willing to look over her crimes, but only on the condition that he look after Portgas D Ace, and later Monkey D Luffy. While Dadad does grow attached to the D brothers, she considers the hardships from raising them to be worse than any prison sentence.
 * In the Final Fantasy V OVA, Rouge the pirate is offered a pardon in exchange for helping the heroes on their quest.
 * In Suzumiya Haruhi,
 * In Soul Eater, witches Eruka, Risa and Arisa are all captured and forced to connect Spartio to the Book of Eibon.
 * In the Mai Hime manga, Nao joins Haruka's Ori-Hime unit so that her rule-breaking will be ignored. Mai questions whether Haruka will keep that promise.

Comic Books
"Nodwick: Let me get this straight: you damaged public property and that leads to employment? Artax: Odd how that works with governmental entities, isn't it?"
 * Many of the soldiers in Marvel/Epic's Alien Legion were this.
 * In the Spin-Off of Gargoyles called "Bad Guys", Hunter, Fang, Dingo, Matrix, and Yama are formed into the Redemption Squad. This was originally supposed to be an animated spinoff, but the show got cancelled.
 * Marvel Comics blatantly stole the idea of The Dirty Dozen for its war book Combat Kelly and the Deadly Dozen. It's in the name - can't get much more blatant than that.
 * The '80s version of DC Comics' Suicide Squad featured an assortment of supervillains sent on black-ops missions by the government in exchange for pardons. This version was featured on Justice League Unlimited as "Task Force X" in the episode of the same name.
 * 'Task Force X' is the 'official' name of the Suicide Squad in the comics as well. One would assume it was changed for much the same reason as Slade Wilson, aka Deathstroke the Terminator, became just 'Slade' on the Teen Titans cartoon.
 * Intentional or not, Who would join a group called the "Suicide Squad" anyway if they valued their lives?
 * Considering that Deadshot was about to be executed, joining the "Suicide Squad" with the option of possibly surviving is a lot better than staying in jail with no possibility of surviving.
 * Of course, it should be noted that the Suicide Squad was (or at least has been retconned to be) a nickname rather than an official designation. So the question you should be asking is "why would someone call this group they've joined the Suicide Squad?" That question has a much more obvious answer.
 * The "Suicide Squad" nickname came about because the odds of surviving long enough to get a pardon are not good. However, the odds of surviving if you decline an invitation are worse.
 * Plus the fact that many of the squad members were borderline suicidal.
 * The latest reinvention of Marvel Comics' Thunderbolts is as a team of former—and not-so-former—supervillains sent to apprehend superheroes who don't obey the Super Registration Act introduced in the Civil War Crisis Crossover.
 * And an even more recent reinvention has the new recruits coming directly from The Raft a.k.a. Alcatraz for supervillains.
 * The DC Comics series Hunter's Hellcats had a very similar premise to Garrisons Gorillas (see below).
 * The Punisher was given one of these offers by a Mafia don who wanted him to keep the old neighborhood safe.
 * Hmmm... approached by mysterious figure... Check. Government offering amnesty for past wrongs... check. Deniability... check. League of Extraordinary Gentlemen, anyone?
 * Kurt Busiek's short-lived The Liberty Project is an earlier example of super-powered criminals in this trope. Unlike most other examples, it's completely above-board, and done at least partly in the hope of rehabilitating the criminals.
 * In Nodwick the party got one quest this way.

Fan Works

 * In Christian Humber Reloaded, the main character, after turning himself in to the police for murdering Soku and her family, is given the job of hunting down or killing convicts, which he enjoys considerably. The webcomic has a brief scene in which the warden acknowledges that this is a very bad idea.
 * Used in many a Doctor/Master fic.
 * In the Red Jewel Diaries of MGLN Crisis, some of the Numbers who are still imprisoned- - get a mission from Auris while in captivity. The others are essentially free, but still reporting in for probation hearings, at the start of the main stories.
 * In White Devil of the Moon, Sailors Mars and Jupiter, as well as Luna and Mamoru, attack Fate a few times while assuming that she is denying them access to Nanoha for sinister ends. Hayate tells them that assaulting an officer is a severe crime, but they can help the Bureau in lieu of official punishment.
 * Sometimes used in Adventures of the Galaxy Rangers fanfics as Doc's backstory. His Mysterious Past was never covered in-series, aside from Word of God saying he signed on "reluctantly." Seeing as Doc is one of the best hackers (if not the best hacker) in the League...

Film

 * The Rock uses this trope with John Mason, who isn't a crook per se, but a British spy who was captured three decades earlier.
 * In The Dirty Dozen, the eponymous twelve were all on death row or imprisoned for life for crimes committed while in the Army. Major Reisman offers them a full pardon - if they survive an almost-certain-death mission.
 * Chicken Run: Ginger gets Rocky to teach the chickens to fly in exchange for hiding him from the circus he escaped from.
 * XXX: Xander (Vin Diesel) works for the NSA or goes to prison for Grand Theft Auto. (No, not that Grand Theft Auto.)
 * His replacement in the second movie, Stone (Ice Cube), was broken out of prison and put to work saving the President.
 * In the French classic Nikita, a woman is recruited from death row to become an assassin by means of a fake lethal injection.
 * Remade for America as Point of No Return.
 * Played with in Kim Basinger vehicle The Real Mc Coy, with the protagonist on parole and trying to go straight. A criminal organization threatens to void her parole unless she aids in a heist.
 * Escape from New York: Air Force One crashes inside the Manhattan penal colony. Prisoner and Former war hero Snake Plissken is offered his freedom if he can get the President out in under 24 hours.
 * Snake has to go through this again to rescue the current president's daughter in Escape From L.A..
 * Both times, it's not specifically the people but the objects they're carrying. The President in the first film has a tape with the secret of on it. The President's daughter in the second film has a controller for a.
 * This is applied to the American military in The Sand Pebbles and the British military in Atonement, with characters given the choice of jail time or military service.
 * The Proposition: "I wish to present you with a proposition..."
 * In Between Heaven And Hell, Sam Gifford (Robert Wagner) beats a lieutenant to death after he accidentally machineguns three of his own men. Becuase he is a Silver Star recipient, at his court martial Gifford is offered the choice of being sent to Leavenworth or being transferred to to George Company, a de facto punishment company in a dangerous area of the line. Gifford chooses George Company.
 * In Rambo First Blood Part II, John Rambo is offered a commuted sentence in exchange for looking for POWs in Vietnam.
 * This describes one of the protagonists of the French action movie Banlieue 13.
 * The titular character in Kurosawa's Kagemusha is a thief saved from execution in order to act as a top-secret double for an identical-looking feudal warlord. How could THAT possibly go wrong?
 * The original The Inglorious Bastards has a bunch of escaped U.S. Army prisoners stumbling across an Allied undercover mission, which they inadvertently foil. To make up for their mistake and secure their release, they take the original crew's place.
 * In a movie of the voyages of Sinbad the Sailor, at one point he is having a lot of trouble getting a crew for his ship because the place he's planning to go to is so dangerous. Finally, he cuts a deal with the government that any convict who agrees to work on his ship will, if he survives the voyage, be pardoned. However, this results in a mutiny since most of his crew are not the loyal type...
 * Virtuosity: Denzel Washington's character is given this deal to try and catch Sid 6.7, but is implanted with an explosive device so the police can just kill him if he goes rogue. Except that his police force ally destroys the software to do it just as they're about to execute him.
 * The main character in Play Dirty is chagrined to discover that the "military unit" he's been given to command on what is essentially a Suicide Mission are nothing but a bunch of convicts given their freedom in exchange for serving as an unofficial special forces division.
 * The Sukeban Deka films, their anime incarnation, and the anime series revolve around a delinquent Japanese schoolgirl fighting crime.
 * Animal Kingdom has Detective Roache, a boxed Corrupt Cop, who's... encouraged to assassinate Joshua, who's under witness protection. The person ordering the hit? Joshua's grandmother.
 * The lead in Point of No Return is saved from lethal injection to become a highly trained assassin. She doesn't want to cooperate but since the alternative is lethal injection...
 * This is the option given to a captured IRA sniper in The Jackal.
 * In The Core, Rat is a young hacker who gets caught violating his parole and is facing some serious jail time. He is offered full pardon (and some other insentives) to help the government cover up the mission. Slight subversion in that his home is raided specifically because they need him. He just happens to be back to his own tricks.

Literature

 * In Terry Pratchett's Discworld novel Going Postal, con artist Moist von Lipwig, after his apparent execution ("apparent" thanks to Lord Vetinari, the Patrician of Ankh-Morpork), is tasked with getting the Ankh-Morpork Post Office up and running again. Two books later, as Moist is getting bored with the post office (practicing breaking into it, even though he has all the keys, for example), Vetinari plucks him up again and sets him to fixing the banks.
 * This happens twice to a master forgery artist, once by Moist and once by Vetinari, in Making Money.
 * It should be noted that Moist's Evil Counterpart from Going Postal was offered one at the end of the book.
 * To some extent, both the first two Hannibal Lecter novels (Red Dragon and The Silence of the Lambs). Instead of a pardon, which is out of the question, he wants information about the private lives of his interrogators.
 * However, since he is Hannibal Lecter, the end result is the same as if they had just left the door to his cell unlocked.
 * In The Stainless Steel Rat, a society that has all but obliterated crime (by catching the potential criminals early and "reforming" them) finds itself ill-equipped to deal with the few criminals who slip through the cracks. So an organization captures the more "moral" criminals (those who value human life) and sends them off to tackle the less moral criminals who pose a more significant threat. Minus A Stainless Steel Rat Is Born, this is the backbone of almost all the books, starting with our hero's capture by the agency in the start of the first book. Oh, and he meets his wife, an insane Serial Killer, via his new job, and after she has a minor lobotomy, she joins up too.
 * Said minor lobotomy does involve needing to know why she's an amoral psycopath, so there's at least a possibility that it's a relatively humane version. She's still casually violent afterwards- but only for a good cause.
 * Frank Abagnale, author/protagonist of the book and movie Catch Me If You Can, ultimately went to work for the Feds to help them spot check forgeries.
 * An unnamed Boxed Crook is used in Personal Demon by Kelley Armstrong to pose as another character.
 * The basic plot of Raymond E. Feist's Shadow of a Dark Queen, complete with slightly sadistic sergeant.
 * Sean Dillon, Jack Higgins' most frequent hero, is an ex-IRA member who goes to work for British intelligence after he's caught smuggling missiles in the Balkans.
 * Also by Higgins, though written under the name James Graham, was The Wrath of God, with a team of three boxed crooks, including the narrator (another ex-IRA man), in 1920s Mexico. One of the three was a defrocked priest who usually pretended he still was clergy — until the time came to pull out his Tommy gun. "That was one hell of a mass, Father!" It was made into a movie with Robert Mitchum as the "priest."
 * In the Stephen King short story The Jaunt, a prisoner on death row is offered the chance to walk if he agrees to make a dangerous trip through a new teleportation system. It turns out
 * This is the entire plot of Poison Study by Maria V. Snyder- the heroine becomes the Commander's food taster.
 * The novels by Sven Hassel about the (fictional) 27th Penal Panzer Regiment.
 * In Red Seas Under Red Skies, the archon poisons Locke and Jean and bribes them to work for him with the antidote. This does not work out well for anyone.
 * In The Destroyer this was the set up for Remo Williams joining C.U.R.E. after they framed him for murder.
 * The X Wing Series has the Rebellion actually go to an Imperial prison planet, raid it, take the Rebels, and tell the surviving members of the Black Sun criminal organization that if they want out, they have to help the Rebel Alliance take Coruscant from the Empire. If they do help, the slates will be wiped clean; past offenses will be ignored. Later on, once they're actually on Coruscant, a Space Cop turned Rebel pilot tells the man he put away that if he doesn't behave he'll be hunted down again.
 * To nobody's great surprise, they end up turning on the New Republic before the end of the book. This is about as conducive to their well-being as you'd expect pissed off Rogue Squadron to be.
 * The opening of The Thief by Megan Whalen Turner finds Gen in a dungeon after being caught stealing. He agrees to help find an artifact in order to get out.
 * In the first Artemis Fowl book, the LEP offers Mulch Diggums a reduced sentence in exchange for breaking into Fowl Manor.
 * The UNACO series by Alistair Maclean various other authors is a UN crime-fighting force whose agents are former criminals.
 * The Red Dwarf novel Last Human features a prison that tried to make a planet inhabitable by using convicts. The cons were given a choice between a nightmarish hell made by whatever their subconscious thought was worst or their soul being used to bring a planet to life. The first planet used guilty cons and so was evil. For the second, they framed innocent people and forced them to choose between going back to their own personal hell and finish their sentence or become the next life force of the new planet. This caused the second planet to be plagued by an entity known as The Rage, a tornado thing possessed of the anger of the injustice the innocents had to face.
 * Robert E. Howard twists it in "Rogues in the House". A mysterious figure does approach Conan the Barbarian and offer him a way out in return for an assassination. On the other hand, he does make it clear from the beginning that he's offering a jail break.
 * In Mara Daughter of the Nile, Sheftu, leader of La Résistance, tries to turn Mara into this, believing her to be a slave on the run from a cruel master and promising to not reveal her if she serves him. He has a mini-Heroic BSOD when he realizes the truth: she was bought and employed by his archnemesis and he never had a hold on her. Well, except for The Power of Love.
 * The first Ciaphas Cain novel has him deal with the aftermath of a riot by getting all the instigators as light a sentence as possible (both because he wants to avoid damaging the recently created regiment's morale even further and to get himself a nice, friendly-fire-preventing reputation for putting The Men First ). He sentences the soldiers who actually committed murder in the riots to "death" via penal legion (see the Warhammer 40,000 example in the Tabletop Games section). In the end
 * The highly mischievous Sun Wukong was put in a multi-millennium-long time-out by the Buddha until Guan Yin recruited him to guard the monk Xuanzang on his Journey to the West. What, you thought this was a modern trope?
 * In Colin Kapp's The Ion War, "para-ion transformation" will temporarily turn someone into a Super Soldier of sorts, almost invulnerable to most weapons, able to walk right through Force Fields, things like that. But the procedure is so horrifically painful -- every time -- that only men already under sentence of death are recruited, because anyone else would refuse to go through with it after the first time or so. Well, except for the ....

Live-Action TV

 * The Mod Squad
 * The A-Team's final season deals with the titular heroes being this in nearly every episode.
 * 2000 television show The Invisible Man had a con released from prison by an intelligence agency so he could become a guinea pig and agent by undergoing surgery to give him a gland that made him invisible. In this case, the government didn't break him out for his skills; nepotism got him out, since his brother was the lead scientist of the project. It was only after his brother was murdered and the government realized that nobody else knew how to remove the gland and place it in somebody more suitable that he was drafted as a secret agent.
 * They still have a hold on him in the form of the counteragent, a drug meant to keep Darien from going insane due to a nasty side effect from the gland (that the Big Bad deliberately introduced into it in order to control potential buyers). The flaw is removed in the series finale, but Darien chooses to come back to the Agency to work of his own free will.
 * Season 3 of Heroes has Hiro briefly doing this to a former enemy.
 * It Takes a Thief: U.S. TV series, 1968-70: Suave cat burglar Alexander Mundy, finally captured, is granted limited freedom on the condition that he ply his thieving trade for a U.S. intelligence agency.
 * This was the premise of She Spies, with the added twist that even if they cooperated fully, the girls would be sent back to prison if they failed a single mission.
 * The TV series Garrisons Gorillas chronicled the adventures of a group of convicts recruited into the U.S. Army by the offer of a post-war parole. Commanded by West Point graduate, Lt. Garrison, the "Gorillas" functioned as commandos behind Nazi lines.
 * Happens to our heroes on Hustle about once a series. On every occasion, the authorities are confident they can outsmart Mickey Bricks.
 * The fourth season premiere of Prison Break kicks off the season with this, involving almost every major character.
 * An episode of Dark Angel reveals that Manticore used death row inmates to train their soldiers. If the inmate makes it to the perimeter before the soldiers catch him, he gets to go free. Of course, that doesn't happen.
 * In a later episode, Alec is captured by government agents and ordered to kill three other Manticore escapees in exchange for his life. If he doesn't bring back their barcodes as proof within 24 hours, a bomb implanted in the back of his neck will explode.
 * This is how Toshiko joined Torchwood in the Torchwood episode "Fragments".
 * The whole point of the short-lived series Thieves.
 * In Brimstone, the Devil releases Ezekiel Stone from Hell to capture the 113 damned souls that had escaped. If he returns all 113, he gets a second chance at life. If he fails, he returns to eternal damnation.
 * In the series premiere of Star Trek: Voyager, Tom Paris is let out of prison to help Janeway track down a Maquis ship. (Not that Paris is much of a crook.)
 * The only reason Paris was in the penal colony was because he confessed to making a mistake that got people killed. Originally, it was ruled an accident. Unfortunately for Paris, he has a conscience.
 * The premise of the USA Network series White Collar.
 * This is a less sinister variation than the page description would suggest, though: Neal is working with the FBI openly and on the books as a consultant, not as an expendable resource. At least, not officially expendable. It's not a bad deal for him, really: instead of four years in prison, he spends four years consulting for the FBI and in his spare time he can go where he likes... within the two-mile radius of his tracking anklet, of course.
 * Except when he leaves the radius and hangs out in the bad guy's HQ, to which the Bureau can't get a warrant. Of course, any evidence of criminal activity they may find in the course of apprehending him is perfectly admissible...
 * Also, it was Neal's idea.
 * In the second episode of The Magnificent Seven series, the judge offers Professional Gambler and Con Man Ezra Standish a pardon for his crimes in exchange as acting as one of the town's peacekeepers for thirty days. It seems to have worked out well, since he's still there a couple of years later.
 * Players. Premise of the 1997 Ice-T series.
 * To kill the crew of the Lexx, Prince sends a NASA shuttle on a One-Way Trip with a death row convict he recruited "to do some more maiming, mutilation and murder before entering oblivion yourself." The quickly-dispatched killer is really there to keep the crew from realizing that there's also a ticking nuclear time bomb on the shuttle.
 * The Fixer. A special forces soldier turned Vigilante Man is released from prison to become an assassin for the British government.
 * In Doctor Who in "Flesh And Stone" is this. In "The Wedding of River Song", we learn.
 * The Prisoner has an episode where Number Six is used as one of these without his knowing it.
 * Alias features three major examples. Arvin Sloane spends most of season 3 working with the CIA as part of his pardon agreement after turning himself in, even working as a double-agent within the Covenant. . Nadia Santos is initially recruited into the Argentine secret service as an alternative to prison when she's finally arrested after a several-year-long crime spree (mainly theft and assault) in her teens, which leads to her eventually joining a CIA black ops division. Renée Rienne also appears to be heading this way in season 5, with Sydney offering to secure a pardon agreement in exchange for Rienne working full-time for the CIA,  . Furthermore, there are many other partially-valid examples (such as Rachel, Dixon and Marshall all being recruited into the real CIA, despite having technically been criminals when working for the Shed/SD-6, on the grounds that they had been conned into believing they were already CIA operatives) and more minor straight-up examples (such as Vivica A. Fox's crooked security expert in season 3)
 * Many of the Big Bad's on Burn Notice use Michael like this.
 * Leverage uses this as the basis for its season 3 arc, with a few flourishes.
 * It was more like "Nate will go to jail (again), and his crew will be killed".
 * The Sukeban Deka series, their film incarnation, and the anime series revolve around a delinquent Japanese schoolgirl fighting crime.
 * Hardcastle and McCormick: Ex-con Mark McCormick is arrested for grand theft auto (the person he stole the car from having murdered Mark's mentor to get his hands on it), and newly-retired judge Milton Hardcastle offers to get Mark paroled into his custody if Mark agrees to help him go after criminals who have escaped conviction.
 * Breakout Kings is about three criminals who get one month off their sentences for every escapee they help the US Marshals recapture.
 * In Power Rangers SPD, Z and Jack were initially both thieves doing time for stealing clothes; they considered themselves to be Just Like Robin Hood, the likely reason Cruger offered them the positions of the Yellow and Red Rangers as part of their parole.

Tabletop Games

 * Warhammer 40,000 does this with the penal legions, most notably Colonel Schafer's Last Chancers, who are basically The Dirty Dozen IN SPACE!
 * Dungeons & Dragons module C2 The Ghost Tower of Inverness. The pre-generated team of PC's almost entirely consists of prisoners from the local dungeon given a chance for freedom if they complete the mission.

Video Games

 * Team Korea in King of Fighters is made of two former criminals and their "supervisor" who's intent on reforming them. Since their alternative is jail time, they go along with it.
 * In the backstory of City of Villains, Dr. Carl Egon, a Mad Scientist who was recklessly endangering the citizens of Cap Au Diable and ultimately killed its governor, was captured by Arachnos, publicly executed, and
 * Thomas Standish, aka "The Turtle," helps out Sam over the radio in Splinter Cell: Chaos Theory when a mission is a bank robbery.
 * Gannayev in Neverwinter Nights 2: Mask of the Betrayer
 * A significant portion of the Terran military in StarCraft are convicts guilty of often-horrific crimes who were "resocialized" (read: basically mind-scrubbed and given artificial personalities) and sent into the military. Their new, excessively kind or chipper personae are often noted as quite unnerving to be around by other characters in books set in the 'verse.
 * Then there's Reapers, who are criminals that are so tough they resist resoc, and are sent to train in Reaper Corps. If they serve for full 2 years, they get released...but currently the longest-served is only 6 months.
 * Averted, to an extent, by the Marauder heavy infantry - because they get goodies like grenade launchers, much effort is put towards placing the most (relatively) well-adjusted soldiers in these suits.
 * And there's the Wings Of Liberty campaign's Token Evil Teammate, Tychus Findlay. A former outlaw and one-time partner of Raynor, he's let out of prison in the opening cinematic by order of.
 * Colonization has, as some of the more undesirable colonists, Convicts, which are not as productive as normal colonists. However, give them some rifles and convert them to militia! If they win a few battles, they don't advance in military experience, but become full-fledged colonists and actually useful around the town.
 * In the Chzo Mythos, Trilby is captured sometime after the events of 5 Days a Stranger, and is recruited to the Special Talent Project.
 * Battlefield: Bad Company is a video game portraying a company made up of the men whose offenses within the US Army aren't serious enough for a court martial and as such are used as essentially cannon fodder.
 * At least two of the three main teams in Raizing's Armed Police Batrider - rogue cops and inveterate criminals who just like violence - fit this trope like a glove. The third, made up of powerful psychics held by the government for study, only half: while they were implanted with bombs to be detonated on failure or insubordination, none of them were actually offered anything in exchange for success.
 * System Shock plot started when the hacker was caught breaking into Mega Corp machine. One of bosses offered freedom and a new neural interface if he agree to covertly disable some non-essential components of their space station's AI.
 * Mass Effect 2: You are ordered to recruit Jack, the most powerful human biotic in the galaxy, who just happens to be homicidal, insane and in lockup on The Alcatraz In Space. Unfortunately, the prison warden gets greedy and decides to capture you as well, forcing you to release Jack and every other prisoner in her block. She agrees to work for you in exchange for info on the people who experimented on her - the same group you're forced to work for.
 * In the third game, she appears to be fully reformed and is busy training young biotics on how to best use their abilities to help the Alliance. She comes up with the idea of "biotic artillery". She even stops dropping Cluster F Bombs in her new role as a teacher, unless you tease her about it.
 * Unreal: Return to Na Pali has you return to the planet you spent so much time trying to escape or get Thrown Out the Airlock. Of course, after you've recovered their lost property,.
 * In Halo 2, the condemned Elite being offered the chance to become the Arbiter is a variation of this: it was made quite clear to him that he would die either way. However, by becoming the Arbiter, he would have the opportunity to regain his lost honor, and cleanse himself of his status as a heretic. The Arbiter in Halo Wars appears to be in a similar situation, except he's been doing his job long enough to be a very dangerous physical combatant.
 * He isn't actually guilty of anything. However, somebody has to be blamed for the, so the Prophets take it out on the fleet commander who let it happen. It was a clear Kangaroo Court.
 * Lobelia from Sakura Taisen 3 definitely qualifies. Unlike the rest of her sweet, innocent team, Lobelia fights not for Paris, but for the reduction of her one thousand year prison sentence. Also, fair is fair, as she's responsible for roughly 85% of all crimes in Paris anyway. Oh, and any failure most probably means death.
 * After General Keyser is defeated and captured in Exit Fate, his rival Bast (whom you recruited specifically to outwit Keyser) wants to draft him for your side. Keyser rightfully thinks the idea is ludicruous, but Bast points out two important things - the war is turning, with your side looking to be winning, and Keyser is more concerned about furthering his career than loyalty to a losing side. Bast then adds, "Wouldn't it be interesting to work with me instead of against me?" The General stands no chance.
 * Daveth from Dragon Age is a thief forced to join the Grey Wardens;.
 * Close to the end of the game, you can also do this to.
 * In the expansion Awakening, the majority of your party members are this: Anders is an apostate mage in danger of being captured by the Templars, Nathaniel is in jail for trying to kill you and steal back his family's possessions from your stronghold, Velanna, and Sigrun fled from a battle (considered an unforgivable offense among the Legion of the Dead).
 * Heck, your player is a Boxed Crook if you chose the Mage or City Elf origin; Mage Warden (unwittingly) helped a blood mage escape, and City Elf Warden slaughtered a bunch of rape-happy thugs (and possibly the evil nobleman employing them), and both would have ended up in jail or worse if Duncan hadn't invoked the Rite of Conscription. In short, the Grey Wardens are very fond of Boxed Crooks.
 * Duncan himself in The Calling novel. A pickpocket on the streets of Val Royeaux (especially since he's not even Orlesian). He gets caught by the guards and is facing severe punishment. Luckily for him, a Grey Warden commander happens to be in town and invokes the Rite of Conscription.
 * The .34 update to Dwarf Fortress adds vampires, who infiltrate your fort and drink your useful workers. The intended manner of dealing with them is to have them executed, but their supernatural qualities give them an alternative function.
 * Hans from Fire Emblem Fates is a hardened criminal that the crown prince of Nohr arrested. Garon not only keeps him around for killing off the occasional rebellion, he's actually a general in his army.

Web Comics

 * Goblin Hollow: the motive for their D&D quest
 * In Order of the Stick, Hinjo recruits high-level prisoners to defend the city, offering to reduce their sentences by five years if they do. This example demonstrates the importance of "insurance" and how easily an employer can be screwed over without it- one is hired by an ambitious politician to assassinate Hinjo and the other defects to the Big Bad before she even starts fighting. By contrast, Belkar considers turning on Hinjo but is forced to decide against it due to the mark of justice that only Hinjo can remove- the only incentive for the other two was a reduced sentence. Being a paladin, it is possible that binding "insurance" either didn't occur to Hinjo or would have directly conflicted with his code.
 * In Girl Genius, the second time Othar Tryggvassen, Gentleman Adventurer! was caught and brought to Klaus, the Baron reminds him he's not a cardboard villain, so there will be no deathtraps... but a "job".
 * Of course, the "job" sends him into Castle Heterodyne, which is chock full of deathtraps... and he's also fitted out with an explosive collar, just like every other prisoner in the Castle.
 * The "dirty half dozen" in SSDD were a bunch of hackers that were caught and offered pardons by a shadowy (and under funded) government agency to create the Oracle. Three ended up in jail anyways when they used the Oracle to continue hacking, one was unexpectedly hit by a bus, and the last one ran away.
 * In General Protection Fault, Agent #18 tells Yoshi that if he helps out with running the MuTex to, he won't tell his parents about his hacking.
 * Impure Blood The offer to the Abomination to escape the Gladiator Games.
 * In Tales of the Questor, how the squire was compelled to accompany Quentyn. He reminds Quentyn of that fact when persuading him not to go back to the duke.

Web Original

 * The SCP Foundation's "Class-D Personnel" are convicted criminals sentenced either to life or execution. Unlike most boxed crooks these guys aren't likely to be granted freedom after their missions-they're used exclusively as expendable manpower in dangerous research. Any that survive the assorted testing are terminated at the end of the month. They appear to be specifically chosen so that the scientists don't have to worry about petty morality like they do with their less doomed coworkers.
 * Of course, since a lack of Ds could cause The End of the World as We Know It, they recruit from the general population in the event of a shortage . ..

Western Animation

 * On Space Ghost Coast to Coast, Space Ghost kept Zorak and Moltar as prisoners on his talk show, with Zorak leading the band and Moltar directing.
 * The Villain Episode "Task Force X" from Justice League Unlimited followed the Task Force (see the comics section) in their planned infiltration of the Watchtower.

Real Life

 * Frank Abagnale, author/protagonist of the book and movie Catch Me If You Can and almost undeniably at least a partial inspiration for White Collar, ultimately went to work for the Feds to help them spot check forgeries. Although in reality, unlike the movie, he was paroled normally before ever consulting for the Feds. At the same time he also began consulting for the private sector and began making rather large amounts of money.
 * Truth in Television: Penal military units were commonly used during the Second World War.
 * Especially dangerous in the Soviet Union, where common criminals were given the chance to 'redeem' themselves by entering penal battalions. Many of them just committed new crimes in hopes of being sent back to prison where their chance for survival was greater.
 * Best way to catch a hacker? Have someone who thinks like a hacker. Best way to have someone think like a hacker? Hire a former hacker. Happens to many criminals to help find a flaw he would look for in his employer's plan.
 * On occasion, hackers have actually hacked their desired employer, as a sort of job interview. One that the employer didn't know about. It tends not to go so well; most so-called "hackers" who find a job this way are normally just professional web developers using nothing but the View Source function of their browser and perhaps an ordinary network traffic-analysis tool. Gaining access to confidential information this way is not going to make you popular, even if the only thing you do with it is email the company's tech support centre with a warning.
 * Eugène François Vidocq embodies this trope: after having been sentenced to death, he bargained his life for his cooperation with the police as an informant. He then organized the Brigade de la Sûreté, which was to become the famous Sûreté Nationale under Napoléon, and spent his last years leading a detective agency.
 * The French Foreign Legion was famous for not asking too many questions of its recruits. Those who survived their tour of duty were rewarded with French citizenship and new identities, so this was a possible exit from a life of crime. Nowadays they have tightened up their recruiting policy and no longer accept known criminals.
 * In the days of early vaccine, some royals had criminals vaccinated to ensure they wouldn't catch the illness from it before giving it to their family (if they survived they wouldn't be hung, although there was at least one case of a criminal who already survived the disease in question).
 * The Englishman, Eddie Chapman was a career criminal who was caught up by Nazi occupation in WWII while doing a stint in a Jersey island prison. He offered his services as a possible Nazi spy so he could get out and get back to England. With a rap sheet that could land him 14 years in prison if he was ever found by the British authorities and the ease he could blend into the English culture, the Nazis accepted Chapman's offer and spent a good chunk of 1940s cash to train him in espionage. The trope was later subverted however when, over his time training with the Nazis, Chapman changed his mind and immediately sought out MI5 when he landed in Britain so he could be used as a double agent against the Germans.
 * Isaac Boro led a failed secessionist struggle against the Nigerian Government in the 60s, for a "Niger Delta Republic". When, in 1967, the more serious secession of Biafra led to the Nigerian Civil War, the Federal Government released him in exchange for military service. He led a group of commandos familiar with the dense Niger Delta Rainforest, and was instrumental in the Federal Army's retaking that region. During a battle where his unit was mixed in with Federal troops, he was shot in the back of the head.
 * The South Korean Unit 684 was composed of petty criminals and unemployed youths, brutally trained and sent to kill the North Korean leader. However, relations improved and the mission was cancelled, leading to a mutiny and the unit being exterminated. It had a movie made about it, Silmido, which was pretty good.
 * George Steinbrenner apparently spent years as an FBI informant to avoid prosecution for illegal contributions given to Nixon until he was granted a pardon at the end of Reagan's term.
 * Armin Meiwes, the notorious German computer repairman who murdered and cannibalized a man whom he claimed gave him consent to do so, also claiming to have a fetish regarding such an act. Now serving life in prison (having become a vegetarian), Meiwes has aided the police in similar murder cases, claiming there 800 men in Germany who have fantasies similar to his, a rather frightening concept.