5 Criminals Who Became Famous Entrepreneurs

Many criminals have failed to complete a formal education, another thing that’s been debunked as necessary for success.

It’s pretty clear that depending on your level of skill, crime really can pay. A lot. Drug trafficking, murder-for-hire, car jacking, check fraud, and identity theft are all booming industries right now. Many criminals have failed to complete a formal education, another thing that’s been debunked as necessary for success. Intelligent deviants who choose a life of crime often profit — and sometimes, they go legit and become incredibly successful in business. Here are five criminals who became entrepreneurs.

Judge Mathis

Although not nearly as entertaining as Judge Judy, Judge Mathis is a popular and well paid daytime television judge. Instead of enforcing the law, Mathis routinely broke it as a teenager. In his high school years, he joined an infamous Detroit street gang called the Erroll Flynns. At age 17, Mathis was arrested and sentenced to prison time after the judge saw his heap of past arrests. Mathis had had enough of crime.

Upon his release, Mathis attended college and became a campus activist. After graduating, he went on to become a court judge for Michigan’s 36th district and never looked back. His show has now been running for ten seasons (since 1999), taping over 2000 episodes. Mathis’ laid back, jovial attitude has gained fans who love his sense of humor. Not only does he allow long, angry diatribes by the disputing parties, but he often lets aspiring rappers and singers showcase their talents for a few seconds during the show. What a guy.

Tim Allen

Yes, really. Before becoming famous for the quirky show Home Improvement, Tim Allen Dick (his real name) was an avid lover of cocaine. That’s not to say he gave up the stuff once on the show — just that he stopped getting caught. In 1978, Allen was caught trying to board a plane with over a pound of cocaine. Instead of taking the mandatory life sentence, Allen Dick ratted out 21 accomplices and got off with only five years prison time.

As most people would, Allen dropped the ‘Dick’ from the end of his name and began doing standup on a dare. When the crowd loved his ‘lovable loser with tools’ persona, he developed it into what would eventually become Home Improvement.

Although he became very successful, Allen didn’t leave his Dickish ways behind him. In 1997, Allen drunkenly crashed his car into a 72-year-old man… and then sued the guy for “damaging his well-known and well-respected name.” Allen dropped the lawsuit after learning the man had brain cancer. He actually went on to call this a humanitarian gesture.

Ironically, Allen’s dad was killed by a drunk driver. This didn’t stop Allen from getting arrested again on a DUI in 1999 for literally falling over during a sobriety test. So maybe he turned around — and then turned back around.

Jay Z

Jay Z started out as a drug dealer in Brooklyn’s Marcy Projects who shot his own brother over stealing his jewelry. Today, he’s one of the richest guys on earth and really knows how to run a business. Jay Z has released multiple rap albums, many of which are considered ‘landmarks’ of the rap music genre. He’s had four number one songs on the Billboard Hot 100. Jay Z owns clubs in multiple cities, will be partial owner of the soon-to-be Brooklyn Nets, has a stake in Roca Wear, is a partial owner of the NJ Nets, and owns an investment company which has equity in a number of odd but profitable ventures. Combined with wife Beyonce, the couple has a value of around $150 million dollars.

Danny Trejo

Danny Trejo could win a Grammy with zero acting skills whatsoever. All he has to do is stand around and stare at stuff to look pensive, terrifying, badass, and/or angry. He used his intimidating appearance to rob convenience stores and was in trouble so much that his own mother “stopped being surprised” when the cops would show up at their house. After his drug habits and life of crime landed him in prison for 15 years, Trejo decided to do something better with himself.

Trejo learned how to box and took a 12-step program to get clean and stay that way. One of his friends in the program happened to be a film production assistant, and asked Trejo if he could ‘look like a convict’ for a role in Runaway Train. Of course he could. Trejo has been in 124 movies since then, always playing the same character but never becoming uninteresting or trite.

Georgia Durante

You may not have heard of Georgia Durante, but her story is the most badass one in this list. A model by 12 and nationally known as the model for Kodak by age 17, Durante was legit from the beginning. She turned to a life of crime after marrying mob man Joe Lamendola, who convinced her to become the getaway driver for many of the mob’s crimes. Durante learned tricks, stunts, and all-around crazy driving moves to elude the police.

It came to an end when Durante decided she had finally had enough of her husband’s abusive ways. During her divorce, she testified against many of the criminals she used to work for and with. Consequently, Durante started her own performance driving school and wrote a book about her life experiences. Her company has been used for the stunts in over 100 films, and Durante has personally been the body double for Cindy Crawford and Priscilla Presley.