The most notorious criminals, of course, never make it out of prison, serving life sentences one way or another. The ones who do go on to freedom, though, have to do something. And some have made more … interesting choices than others.

John Hinckley, Jr.

Hinckley on YouTube

(YouTube)

Following his attempted assassination of Ronald Reagan in a bid to please a famous teenage lesbian on March 30, 1981, John Hinckley, Jr. was locked up in a psychiatric facility until 2016 and immediately began securing what he hoped would be his true legacy: a musical career. At first, he had to post his songs anonymously, but after a judge ruled in 2020 that the sale of his music and art wouldn’t technically be profiting from his crimes, he started a YouTube channel that has gained 26,000 followers. YouTube was even monetizing his videos for a while until one of them went viral and put them in a compromising position.

Anna Sorokin

The “Fake Heiress” is still being held by ICE, but during her brief moment of freedom between her 2021 release from prison and the discovery of her expired visa, she went right back to the good life, checking into a hotel and hiring a camera crew to follow her around for vague reasons with all her Netflix money. She’s also made a deal with the Real World people to make a reality TV show and plans to write a book and create a podcast, A.K.A. the modern triple threat.

Al Capone

Capone in 1930

(FBI/Wikimedia Commons)

Capone was only released from Alcatraz in 1939 because his brain was falling apart from syphilis, the least desirable “get out of jail free” card. He might have liked to return to his Chicago empire, but by 1946, he had the mental capacity of a 12-year-old, and no one wants a preteen running their mob. Despite treatment and even being one of the first people in America to receive penicillin, he never improved, living out his days on his Florida estate with his family as a tween trapped in an old gangster’s body.

Karla Homolka

Scene from "Karla"

(Christal Films)

Karla Homolka, who helped her then-husband rape and murder several teenage girls in the early ‘90s, was released after 12 years in prison in 2005 and married her lawyer’s brother shortly thereafter, but being one of the most hated people in Canada hasn’t made post-prison life easy (it takes a lot for those people to hate). She tried working at a Montreal hardware store, but her boss doxxed her to the media, and volunteering at her children’s school, but community outrage put the kibosh on that, too.

Charles Ponzi

Ponzi in 1920

(Boston Library/Wikimedia Commons)

After he was released from prison and deported to Italy in 1934, the man with his own scheme named after him kept right on scheming, according to one account that he conned his way into a lucrative job with Mussolini’s government and then fled with the cash. He might have also gone legit in the airline business with the help of a relation who had connection to the Italian Air Force and Mussolini, later teaching English and French and doing translation work after World War II. Either way, Mussolini was involved.

Eddie Nash

Eddie Nash, long implicated in the Wonderland murders portrayed in Boogie Nights and several lesser films, never actually caught any heat until the 2000s, when he pleaded guilty to money laundering and wire fraud. By then, he was in his seventies, living the peaceful retired life in suburban Los Angeles with his adult children, to which he returned after serving only four and a half years in prison.

John Wojtowicz

Al Pacino in "Dog Day Afternoon"

(Warner Bros.)

John Wojtowicz, played by Al Pacino in Dog Day Afternoon, didn’t fare as well from the movie about his failed bank robbery than most people who get movies made about them. He was only paid $7,500 for the rights to his story, which largely went to his legal fees and his girlfriend’s gender confirmation surgery. She left him while he was in prison, claiming she’d never loved him, and by 2001, he was living on welfare in Brooklyn.

Patrizia Reggiani

Patrizia Reggiani arrest photo

(Milan Police Department/Wikimedia Commons)

The black widow of couture who ordered the murder of her husband, Maurizio Gucci, met a fate possibly worse than prison for a Gucci following her release: designing for Bozart, a Milanese company known for its tacky costume jewelry. The Cut speculated that Bozart only hired her for the publicity it would bring them, which was a real monkey’s paw situation once they found out what dealing with Reggiani was actually like. “Oh, mamma mia, it’s not easy,” one of the owners told reporters, Italianly.

Sylvia Likens’s Murderers

Gertrude Baniszewski in court

(Indianapolis News/Wikimedia Commons)

Gertrude Baniszewski, played by Catherine Keener in An American Crime, served a shockingly short sentence of only 19 years for the months-long torture and murder of Sylvia Likens, a teenage girl in her care. She died five years later, insisting the whole time that she couldn’t remember the ordeal. Two of her children, who also participated in the abuse, ended up working for schools, so that’s fun (although one was fired after her employer found out who she really was).

Bruce Reynolds

No one involved in the 1963 U.K. Great Train Robbery served much time, even mastermind Bruce Reynolds, who served only nine years. After his release, he said he “became an old crook living on handouts from other old crooks," but he wrote nine books and made an appearance in a song about him by the band who played the Sopranos opening credits song, Alabama 3, of which his son happens to be a member.

Charles Colson

Colson with George W. Bush in 2008

(White House/Wikimedia Commons)

After former White House special counsel and Nixon’s personal “dirty tricks” man Charles Colson went to prison during the Watergate scandal, he got born again and founded a prison ministry as well as “the nation’s largest religion-based criminal justice reform group.” He played a pivotal role in uniting America’s various religious communities under a right-wing umbrella, so, you know, blame him.

Frank James

James in 1898

(Library of Congress/Wikimedia Commons)

Jesse James’s fraternal sidekick capitalized on his post-crime fame in some unusual ways. While working as a ticket-taker for a burlesque theater, an occupation you’d think you’d keep low key, the theater used the lure of getting “your ticket punched by the legendary Frank James” as a selling point. Later, he offered tours of the James family farm, where Jesse was buried, for 25 cents. You could even get a souvenir pebble.

Top image: YouTube

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