They could have had him any day
They only let him slip away
Out of kindness, I suppose.
An Outlaw who is trying to add "former" to his description.
Let's face it, the outlaw life isn't for everyone. Sure, being outside the law gives you freedom, but you face freezing, starvation, getting ventilated by bullets on a regular basis, and you can forget about establishing normal relationships when you have to be able to get the hell out of town on a moment's notice. So some outlaws try to go straight.
In fiction, they generally break down into two broad categories.
- Outlaws who have successfully pulled off that fabled One Last Job and then try to go directly from "fugitive" to "law-abiding citizen" with no steps in between. Generally this involves Starting a New Life: changing his name, moving to a different territory, or otherwise obscuring his identity. How well this works depends on the story, but usually at least the main characters (who may be their former partners in crime) will discover the retired outlaw's secret.
- Former outlaws who've served their time in prison, paid their debt to society, and just want to put it behind them. These generally appear in stories returning to the same territory where they committed their crimes, as that's where their wife or surviving relatives live. The Untrusting Community certainly hasn't forgotten the former outlaw's foul deeds, and often they haven't forgiven them either. Sometimes the retired outlaw can earn the town's trust and grudging respect, sometimes not.
It's not unheard of for former Outlaws to become lawmen, the most famous case being Wyatt Earp.
This trope often overlaps with Retired Badass and Retired Gunfighter, but doesn't have to. Some outlaws retire specifically because they don't have the badass attitude necessary to succeed in the field. Compare I Just Want to Be Normal for a similar mindset. If the outlaw was particularly bad, and shows no remorse for past actions, he may be a Retired Monster.
- Love Freak Miyu from Super Gals is a former gang leader. When the show starts she's dating the police officer who arrested her...
- Habara a.k.a. "Archdemon" in Daily Lives of High School Boys is a reformed bully. She's a rather plain girl by the show's beginning, but she has yet to live down her past.
- Taking place in a world of pirates, One Piece has plenty of these. Some are nice, some aren't...
- Captain Kuro grew bored with the high-stakes life of being a wanted outlaw, and faked his death so the Navy would leave him alone. Of course, that didn't stop him from plotting to steal someone else's fortune...
- After he lost his crew and leg, "Red-Leg" Zeff started the Ocean-Going Restaurant Baratie.
- Crocus used to act as a ship's doctor on the Pirate King's crew, but following the crew's disbandment, went back to Reverse Mountain and Laboon.
- Silvers Rayleigh was once the first-mate to Gold Roger himself, but now works at the Sabaody Archipelago, coating ships heading underwater with protective bubbles.
- In at least one of the Masked Raider stories in Marvel Mystery Comics, the sheriff is a retired outlaw who is blackmailed into letting the gang do what they want because they know his sordid history.
- Wonder Woman: In her old age Priscilla Rich, the first Cheetah who operated as a villain in the 1940s and '50s, comes off like this. She's served her time, tried to prevent her niece from becoming the second Cheetah and condemns Barbara Ann Minerva's actions as the third Cheetah. Barbara ended up hunting her down and murdering her in her quest to become the only Cheetah despite Priscilla's advanced age and retirement.
- Both Clint Eastwood and Morgan Freeman's characters in Unforgiven.
- Once Upon a Texas Train has a band of retired outlaws who are reunited for one last job when their leader is finally released from prison.
- Butch Cassidy and the Sundance Kid try to do this by becoming bodyguards. They go back when their legitimate employment comes with a much higher body count.
- The Gunfighter has two men who do this. One succeeds, the other fails. The one who succeeds becomes a town marshal.
- Young Guns II (in one of its great number of historical inaccuracies) portrays Pat Garrett as a Retired Outlaw who was part of Billy the Kid's group before being recruited into being a lawman and hunting Billy for the local authorities.
- In Shanghai Noon, we have Roy O'Bannon, who starts the movie as an outlaw but by the end of the movie he's softened up . The epilogue reveals that he has become a lawman, and that his real name is Wyatt Earp.
- Ronald in The Warrior's Way.
- The title character of The Grey Fox is a former Wild West stagecoach robber who, after spending 33 years in prison, moves to a small town in British Columbia in the early 1900s to quietly spend the rest of his life as a law-abiding citizen. However, while there are no more stagecoaches to rob, trains soon prove to be an all-too-tempting target for the restless retired outlaw.
- Robin and Marian: At the start of the film, Robin and Little John return to England as this but quickly get drawn back into their old lifestyle when the Sheriff tries to kidnap Marian.
- In Johnny Reno, U.S. Marshal Johnny Reno is a former outlaw turned lawman. And he seems very happy in his new position, showing an immense respect for the letter of the law.
- Rachel is one at the start of Gang of Roses. She straps her guns back on when her sister is murdered.
- In Mystic River Jimmy Marcus was a juvenile delinquent and later the leader of a fairly sophisticated group of thieves. He retired for good after the combination of going to prison and his wife's death while he was inside, leaving him to raise their daughter when he got out, and now owns a convenience shop in town. Although the younger generation has no idea what he did, some of the neighborhood's older residents have never stopped thinking of him as a thief.
- Jean Valjean of Les Misérables is a mixture of both types. He tries to go straight after getting out of prison, but discovers that so long as people know he's an ex-con, they'll never give him a fair chance, so he's forced to create a new identity to become an honest man. This violates the terms of his parole, turning him into a fugitive.
- Wayne in Mistborn: The Alloy of Law used to be a thief before he accidentally killed a man. He was saved on the brink of being hanged by Wax - a lawman - and ended up becoming a lawman himself, if a bit of a Kleptomaniac Hero. He still sends half of his wages to the family of the man he killed.
- In O. Henry's story, "A Retrieved Reformation," the safecracker Jimmy Valentine has gotten out of jail and is trying to go honest under a new identity so that he can marry a banker's daughter. But when a young child accidentally locks herself in the bank's new super-secure safe, he's the only one with the tools and the skills to have a prayer of getting her out.
- In River of Teeth, Hero Shackleby is a retired Demolitions Expert and Master Poisoner who's bought themselves a little house on the prairie and spends their time sipping poisoned iced tea on their porch. Since that has become really boring really fast, Hero jumps at the opportunity Houndstooth presents to be active again and do One Last Job that will make them known far and wide.
- CSI once had an episode where one of the ringleaders of the Rwandan Genocide moved to America posing as a refugee, trying to put it behind him. It... doesn't work out...
- Alias Smith and Jones has two outlaws trying to retire, but forced into the Boxed Crook role in order to get an amnesty offered by the governor of Wyoming Territory.
- Earl from My Name Is Earl tries to do this by creating "good karma" through good deeds, after getting hit by a bus (as a balance for winning the lottery after all his bad deeds). Unfortunately, all the bad karma from before is still conspiring to force him into it. At one point, he loses faith in his list (of things to make up for) and goes back to his criminal practices. He gets hit by a car within a few days.
- While most of the fugitives in Time Trax continued their criminal activities in the 20th Century, one of them took the chance to get a fresh start and became a lawman. He died helping Lambert take down a present-era criminal (as well as teaching him how to quick-draw). His gravestone had a birth date a century and a half later than the death date, and the inscription "He found his place in time."
- Black Saddle is about Clay Calhune; an outlaw whose brothers were killed in a shootout that left him seriously wounded. After recovering, Clay decides to swap his six-guns for law books and becomes a lawyer.
- The Townes Van Zandt song Pancho and Lefty has Lefty, who retired to Ohio after his compadre Pancho was killed. The song implies Lefty sold Pancho out for the reward money as a nest egg.
- There's a kids' song by Tom Chapin called "Billy the Squid" about a squid outlaw who at the end of the song retires to the suburbs with "Clamity Jane" (yes, the whole thing is a Hurricane of Puns).
- "Ringo" by Lorne Greene, the first-person account of a Western lawman, an ex-outlaw, and his relationship with the title character, a notorious gunfighter.
- A storyline in the newspaper comic Latigo concerns an ex-gunman who goes straight after four years in prison, and becomes the preacher in the town of Rimfire. It originally ran in 1981.
- In The Music Man, Harold Hill comes to River City to find that his old partner, Marcellus Washburn, who still knows him as Gregory, has settled down there:
Harold: Besides how could I know you'd end up in a little tank town like this? You were a pretty big slicker when you were in business like me.
Marcellus: Too many close shaves the way you work. Besides I got me a nice comfortable girl—Ethel Toffelmier—boss's niece.
Harold: Gone legitimate, huh? I knew you'd come to no good.
- Jericho in Fallout 3 is a retired raider, although he doesn't seem to be happy living in Megaton. Also, Moriarty speculates Billy Creel might have killed Maggie's parents and "adopted" her. However, considering Moriarty's character, his claims are very suspect.
- John Marston's family in Red Dead Redemption is a textbook example of the "going straight to law-abiding citizen" variety. His new life as a simple rancher went pretty well for him — at least, until the FBI's predecessor kidnapped his family and ordered John to capture or kill his former gangmates.
- Michael in Grand Theft Auto V starts the game as one of these, having settled down, entered Witness Protection, and raised a family using his earnings from his past days as a bank robber. However, he's soon drawn back in by both ending up in debt to a cartel kingpin and the fact that he doesn't feel fulfilled by "civilian" life.
- The same game also gives mention to previous protagonist, Niko Bellic. According to Lester, he "Went quiet" and left his criminal ways behind.
- Rusty in Scrapland used to be a mercenary in his youth, before he got too old. Now he runs the junkyard.
- As mentioned above, several western notables accomplished this in real life. Wyatt Earp and Doc Holliday both switched sides between outlaw and lawmen at various points in their lives. It was easier for a person to start over in eras before computer networks.