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He may share his name with a notorious outlaw, but famous motorcycle customizer and television personality Jesse James never needed to break bad to make a name for himself. Though, he has had his fair share of controversy over the years.

Whether you know him from his TV shows Monster Garage (which is set to return in 2020) or Jesse James Is a Dead Man, his custom motorcycles for Keanu Reeves or Shaquille O’Neal, or his tabloid-fueled relationship with Sandra Bullock, you know that the guy is great at making headlines.

James’ passion for motorcycles at an early age led to a multimillion-dollar enterprise in West Coast Choppers, which eventually spawned a successful television career and several other business ventures. But, after nearly 20 years in the spotlight, the 50-year-old James has managed to withstand the ups and downs by continuing to do what made him famous in the first place: customizing motorcycles.

Early Life and Career

Jesse Gregory James was born on April 19, 1969, in Long Beach, California. His father ran an antiques shop, which was located right next to a Harley-Davidson parts supplier. Thus, beginning his lifelong obsession with motorcycles.

“I remember seeing a pack of Hell’s Angels blasting by our family car when I was about 6, and they were all riding choppers,” James told a Discovery Channel interviewer in 2000. “I remember all the noise and all the chrome. It was the coolest thing I ever saw. I knew then that I was going to be involved in motorcycles in some way.”

When a career in football didn’t pan out after several injuries, James dropped out of college and worked as a bodyguard for bands like Danzig, Slayer, and Soundgarden. In 1992, James opened West Coast Choppers, a clothing line and motorcycle customization shop. After falling off stage during a concert in 1993 and dislocating his elbow, James decided to put all his eggs in the WCC basket. Needless to say, it ended up paying off.

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West Coast Choppers

Starting in his mother’s garage and eventually moving to a small shop in Long Beach, Jesse James would find that success with West Coast Choppers wouldn’t come overnight. In the early days, James found himself overworked and underpaid, and even got the words “PAY UP SUCKER!” tattooed on his palm to express his frustration over money issues.

James’s big break came in 2000 with the Discovery Channel documentary Motorcycle Mania. Giving an inside look into Jesse’s day-to-day life, the multipart series introduced his brand to the masses. West Coast Choppers would move from a one-man crew grinding in a small shop to an organization with more than 50 employees working out of an 18,000 square-foot warehouse.

James would go on to design custom bikes for such A-listers as Shaquille O’Neal, Keanu Reeves, and Kid Rock. With a West Coast Chopper motorcycle fetching anywhere from $60,000-$150,000, we’re guessing James rarely needs to show that “PAY UP SUCKER!” tattoo these days.

While WCC’s Long Beach location shut down in 2010, James reopened the shop in Austin, Texas in 2013.

Television Success and Other Business Ventures

Following the success of Motorcycle Mania and his growing celebrity clientele, James was tapped to host the Discovery Channel competition show Monster Garage. The highly-successful series spawned a UK version, two video games, and a number of books. On top of that, 42 of the surviving project vehicles were sold at the 2008 Barrett-Jackson Scottsdale auction. While Monster Garage only aired from 2002-2006, it is set for a 2020 revival.

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With appearances on Sons of Guns, Celebrity Apprentice, Street Customs, and American Chopper, James also starred on the Spike TV show Jesse James Is a Dead Man, where he performed death-defying stunts. Under his own company Payupsucker Productions, James has also produced such shows as History of the Chopper, Iraq Confidential with Jesse James, and Green Scream.

As far as other business ventures go, James opened Cisco Burger in 2006, right across the street from West Coast Choppers. In lock step with WCC, the restaurant has since moved from Long Beach to Austin. Since 2006, James has nationally published Garage magazine and also owns Jesse James Firearms Unlimited. To say that this guy keeps busy is an understatement.

Read More: Danny Koker: From Motor City Beginnings to “Counting Cars” Stardom

Controversy and Legal Issues

For as much success as Jesse James has enjoyed over the years, he’s had an almost equal amount of controversy. For one, you could write an entire book chronicling his relationship issues alone.

With three children from his first marriage to Karla James, James was married to adult film star Janine Lindemulder from 2002-2004. It was a relationship fraught with drama, including assault charges against Lindemulder and a messy custody battle over the couple’s daughter after Lindemulder’s release from prison over tax evasion charges.

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James later married actress Sandra Bullock in 2005. That marriage deescalated into tabloid fodder following the revelation that James had cheated on The Blind Side star with multiple women while the couple was in the process of adopting a child. To make matters worse during this time, a photo also came out of James in a SS officer’s hat and doing the Nazi salute, though he claimed the hat was a gag gift from his Jewish godfather.

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James and Bullock divorced in 2010. Following the intense fallout from his infidelity, James checked himself into an Arizona rehabilitation facility for 30 days, where he received treatment for anger management and sex addiction.

James is also no stranger to litigation. In 2007, he was fined more than $270,000 by the California Air Resources Board after authorities determined that James’ bikes were in violation of California’s clear air laws and emitted 11 times the legal limits of hydrocarbons. In 2008, James faced two costly lawsuits and was fined $422,680 over a breach of contract with a customer, and later $327,533 for unpaid lawyer fees.

Jesse James Net Worth and Personal Life

Jesse James has an estimated net worth of $100 million. While he’s clearly doing much better from a financial aspect than he was during his early days, he’s also been thriving on the relationship side as well, having been married to drag racer Alexis DeJoria since 2013. Alexis is the daughter of billionaire John Paul Dejoria, the founder of the John Paul Mitchell hair brand and The Patron Spirits Company. Clearly, Alexis didn’t need to marry Jesse for his money.

This post was originally published on March 9, 2020.

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