All the Ways Jesse James Earned His Bad Boy Reputation

It’s been a long time (since the mid-2000s) since Sandra Bullock and her ex-husband Jesse James flooded the media with their messy divorce. But Bullock is just one chapter in this bonafide bad boy’s Book of Babes. This entrepreneur/mechanic has earned himself a reputation of being Hollywood’s resident bad boy and after reading this, you’ll truly see why.

Kat Von D, Jesse James / Jesse James / Sandra Bullock, Jesse James / Jesse James
Source: Getty Images

If anyone suffered from the James-Bullock debacle, it was definitely Bullock. After all, it was James’s infidelity that the media exploited the most. It’s been about 15 years since the fiasco, and James’s private life has consistently made front news headlines (in the tabloids, at least). For those of you who just love dishing the dirt, you’re in the right place. This is everything Jesse James (and I’m not talking about the notorious 19th-century outlaw).

He’s Back at Monster Garage After 14 Years

Back in 2002, Jesse James became the host of a show called Monster Garage. If you’re a fan, then you already know that it’s a show about a group of mechanics modifying cars under a deadline. The series lasted until 2006, but then all of a sudden it was announced that in 2021 the show would be making its comeback.

Jesse James in the set of Monster Garage.
Photo by Anne Cusack/Los Angeles Times/Getty Images

The fame James found himself in after the success of his very own West Coast Choppers and Monster Garage made him seemingly uncomfortable. He wasn’t a big fan of all of the newfound popularity, especially when the media was exposing all of his bad boy tendencies for the world to see. It also didn’t help that he was married to a Hollywood A-lister.

He Started West Coast Choppers When He Was in High School

West Coast Choppers (WCC) started out as a brand of printed T-shirts and stickers. James founded the company in the early ’90s when he was finishing high school. The brand grew to include tools, beverages, and clothing. They even sold motorcycles, but they were only averaging about 12 to 15 choppers a year, which was actually losing money for the company.

A young Jesse James is lying down in his garage.
Source: Instagram /@popeofwelding

The good thing, though, was that they were attracting positive attention (which doesn’t often happen for James). Soon enough, celebrities like Shaquille O’Neal, Kid Rock, and Keanu Reeves were a big part of the WCC brand. By 2010, however, the company shut down. James moved to Austin, Texas, and eventually reopened a new and smaller version of WCC.

His Net Worth Is Around $100 Million

The 52-year-old entrepreneur is a wealthy man, to say the least. His net worth sits at around $100 million, and that’s thanks to all of his business endeavors. And boy does he have a lot. For one, he had a burger chain called Cisco Burger, which sat across the street from West Coast Choppers (it’s been relocated to Texas).

A headshot of Jesse James.
Photo by Ken Hively/Los Angeles Times/Getty Images

He also produces shows under his production company, Payupsucker Productions. He has a culinary knives company, too, by the way. Jesse James Culinary began in 2018. Oh, and did you know that he has a firearm business called Jesse James Firearms Unlimited? James felt the need to take his passion for guns to the next level, and in 2013 he started making custom firearms.

Is He Related to the Famous Outlaw Jesse James?

According to James’s Discovery Channel website, his great-great-grandfather was the notorious outlaw’s cousin. Of course, we’re referring to Jesse James – the one they made a movie about, with Brad Pitt portraying him.

A 500 dollar reward poster for the arrest of outlaw Jesse James / A portrait of American outlaw Jesse James.
Photo by American Stock Archive, Archive Photos, Getty Images / Kean Collection, Getty Images

However, Eric James, the president of the James Preservation Trust, is doubtful. He tracked the outlaw’s genealogy and couldn’t find a record of James in the family tree. He asked the entrepreneur to provide a family genealogy and DNA sample. It’s unclear if James ever did. But let’s just ignore that part for a moment and assume that the Discovery Channel is right.

His First of Four Wives: Karla James

Not everyone knows that Jesse James has been married four times (although it’s not very surprising). His first wife was Karla James, and they were married from 1991 to 2002 and had two children together, a son named Jesse James Jr. and a daughter named Chandler James. Their split was amicable; they have remained close friends and co-parents.

Karla James poses wearing a gala dress.
Source: Tumblr

The fact that they are close only made the news of her illness even more devastating for James. Recently, Karla was diagnosed with early-onset Alzheimer’s and dementia. James, in his grief, reached out to his followers online. He told his fans that he would be taking care of her and the kids since she didn’t have any other family.

His Second Wife: Janine Lindemulder

In the same year that he divorced Karla, James married his second wife, stripper/adult film actress/producer Janine Lindemulder. They were married for a couple years, from 2002 to 2004, and had a daughter together.

Janine Lindemulder is escorted into a Justice Center by Orange County Sheriff Deputies.
Photo by Jerod Harris/Getty Images

In 2009, Lindemulder, who at that point had been in federal prison for six months for tax evasion, tried to regain custody of their then five-year-old daughter Sunny. Sandra Bullock, his next wife, stood by him as he went through a bitter and long custody battle with Lindemulder. In 2009, James won the battle and was granted full custody of the child.

This only leads us to wife number three – the most famous of them all…

Third Time’s a Charm? Not With Sandra Bullock

A year after his divorce from Lindemulder, James went for his third wife, Sandra Bullock. Bullock and James were married for five years, from 2005 to 2010, but their tale began in late 2003. At the time, Bullock arranged for her godson to meet James because he was a fan of Monster Garage.

Sandra Bullock wraps her arm around Jesse James.
Photo by Eric Charbonneau/WireImage/Getty Images

Sparks flew between the actress and the motorcycle fanatic and, before long, they were dating. In the summer of 2005, Bullock and James walked down the aisle, not long after they adopted their son Louis. For a while there, everything was looking up for both of them. The sun was shining; the weather was sweet…

And then…

The Messiest Breakup in Hollywood

Bullock and James managed to find themselves involved in what might be the messiest breakup in Hollywood history. After a five-year marriage (seven-year relationship), everything blew to pieces when rumors began to surface about James cheating on her.

Sandra Bullock points her finger to Jesse James during an event in an auditorium.
Photo by Christopher Polk/Getty Images

In retrospect, we should have probably seen it coming. But the two really seemed like the perfect couple at first. On the red carpet, the celeb pair looked like a match made in heaven. Bullock was marrying into a packaged deal, too, becoming the stepmother to James’s three children. In those days, Bullock asserted that she loved her husband’s kids as if they were her own biological children.

Trouble in Paradise

By March 2010, the scandal emerged when several women professed their illicit relationships with James while he was married to Bullock. One of those women was model Michelle “Bombshell” McGee. Afterward, other women started speaking up.

Michelle Bombshell McGee poses for a portrait on the beach.
Photo by Larry Marano/Getty Images

The TV personality didn’t shy away (if that makes a difference) and issued a public statement to Bullock: “There is only one person to blame for this whole situation, and that is me.” As soon as all the cheating scandals were exposed, everything took a turn for the worse.

An Ugly and “Unfair” Divorce

Soon after the rumors began, the actress moved out of their California home and started the ugly divorce process. As a result, James lost custody of their adopted child. James was quoted as saying, “Whether that’s fair, whether I should have lost a kid due to infidelity, which I don’t think anybody ever does. But I think with Hollywood Law that’s totally fair.”

The press spots on Sandra Bullock and Louis Bullock going out of the car.
Photo by Jacopo Raule/FilmMagic/Getty Images

The most upsetting part about his split was losing his son – and not being able to see him grow up. According to James, his infidelity caused a heck of a lot of shame and embarrassment for Bullock and the rest of his family.

He Tried to Work on Himself to Get Her Back

The whole thing caused his wife and kids “pain and embarrassment beyond comprehension,” he stated. James’s apology placed the blame on himself. His publicist announced around that time that James had checked himself into a rehabilitation facility to work on his personal issues. In April 2010, he went to rehab for sex addiction.

A close-up on Sandra Bullock while Jesse James stands far in the background.
Photo by Kevin Winter/Getty Images

Apparently, he was hoping to save his relationship with Bullock. But then he went on the Howard Stern and said some things that not only contradicted this but added even more hate to the already messy debacle.

He Says He’s a Victim of Child Abuse

According to an exclusive interview with ABC’s Nightline in 2010, James claimed that he is a victim of child abuse. James cited his shame and lack of self-worth for driving him to cheat on Bullock and destroy his fairy-tale marriage.

A young Jesse James sitting outside working with his hands.
Source: Instagram /@popeofwelding

“I grew up with a huge amount of shame and fear and abandonment on my shoulders from a very young age,” he explained. The way he reasoned it, he needed to do whatever he could to run her off because she was going to find out who he was and leave either way.

Rehab Was an Eye-Opener for Him

The then 41-year-old said he slept with multiple women and that it stemmed from his own emotional shortcomings. This new insight came after his stint in rehab, where he walked in with “a little bit of an ego,” but learned to open up and figure himself out.

Jesse James sits outside and drinks an orange juice.
Source: Instagram /@popeofwelding

Every day, he had a new revelation about himself and the things he had been doing: “I cried more in rehab in the last 30 days than I have in my whole life. No BS. That’s the truth.” He was there for a month to receive treatment for sex addiction and anger management, but he also touched on the childhood abuse.

30 Years of Repressed Memories

According to James, rehab forced him to confront repressed memories from 30 years ago that he never realized had had such an impact on him. All the choppers, building, the bad boy image – it’s just a “huge smokescreen” for people not to see him for the “scared, abused, seven-year-old” he is inside.

A young Jesse James sits on his bike wearing a helmet and gloves.
Source: Instagram /@popeofwelding

James was raised by his father, the man who was (allegedly) physically and emotionally abusive. He would beat James, and James was always scared of his father. One incident stood out for him – when his dad chased him in the dark.

He Was a “Terrorized Kid”

He recalled tripping over a low fence wire and snapping his wrist as a result. His dad laughed at him when he hit the ground, calling him a “dummy,” James remembered. It was less the actual beatings but rather the “in-between time” that terrified him the most.

An old memory of young Jesse James enjoying a day out with his family.
Source: Instagram /@popeofwelding

He was in constant fear of it happening again. “I was a terrorized kid,” he described, all the while tearing up when recalling these events. James’s father, Larry James, wrote an email to ABC News claiming that his son’s allegations aren’t true.

He Never Felt That She Loved Him Anyway

James may have gone to rehab and may have felt enlightened, but old habits die hard. In that Howard Stern interview, he said he never believed that Bullock ever loved him. “I always felt like any moment that rug was going to be yanked out,” he admitted. Even when Bullock made her Oscars acceptance speech (for 2009’s The Blind Side) and announced to the world just how much she loved James, he still didn’t believe her.

Sandra Bullock and Jesse James are sitting among the crowd at a hockey game.
Photo by Stephen Dunn/Getty Images

“Yeah, she could stand there in front of the world and say she loved me, but in my mind, I was thinking, Yeah, bulls***. You don’t love me,” he told Stern. According to James, he didn’t cheat on her right away.

It Took a Few Years for Him to Do It

He confessed that it took a couple of years for him to cheat on her. James acknowledged that he was unfaithful to “America’s sweetheart,” but that he was “still this f***ed up kid from Long Beach.” He did clarify, though, that he loved her and cared about her.

Sandra Bullock and Jesse James are having a conversation at the Academy Awards.
Photo by Kevork Djansezian/Getty Images

“The stuff that I did that was bad; I don’t think it necessarily nullifies everything I felt… The problem was me.” While Bullock never remarried (or at least hasn’t yet), James did eventually give marriage another try. He moved on to wife number four: Alexis DeJoria, the drag car racer.

But, before his fourth wife, he had a scandalous fling with another TV personality…

He Had a Relationship With Kat Von D

As soon as he and Bullock split (which is a questionably short amount of time), Kat Von D came into the picture. James and the famous tattoo artist became a very passionate and complicated couple. They were together for a little over a year and even got engaged; the announcement came in 2011.

Kat Von D and Jesse James attend Jesse James' book signing event.
Photo by Chelsea Lauren/WireImage/Getty Images

Then, suddenly, they called it off. Miami Ink’s Von D went through an ugly divorce of her own – to Oliver Peck, who didn’t have very nice things to say about his ex. In a 2014 interview, Peck said Von D has “done nothing but screw over every friend she’s had” in addition to cheating on him.

They Were Best Friends for Many Years

Peck also didn’t expect much of her whirlwind romance with James. “Who knows if the relationship is just a publicity scam — she’ll do anything to stay in the limelight,” Peck stated. Von D told Access Hollywood that she actually knew James from way back when – when she was 22 years old.

The press spots on Kat Von D and Jesse James as they exit a restaurant.
Photo by Bauer-Griffin/GC Images/Getty Images

“We’ve been friends forever, and this is definitely something that I think we weren’t expecting,” she said, adding that he may even be “The One.” A few months later, they were engaged. James was apparently over the moon in love, being engaged to his “best friend.” So, what happened?

Our Mothers Were Right, Ladies

Kat Von D confirmed the news of their breakup on her Facebook page (this was 2011, remember). “I am not in a relationship,” she wrote. “And I apologize for all the back and forth if it’s caused any confusion.”

Kat Von D attends an event.
Photo by Tara Ziemba/WireImage/Getty Images

The beauty mogul explained that she and James “were just on two different paths in life.” But people had a gut feeling that it was more than that. And yes, it turns out that our mothers were right when they told us – and you can insert your mother’s voice here – “once a cheater, always a cheater.”

The Truth Came Out

The truth came out: James was still adulterous. It turns out James was on one long cheating streak involving extramarital affairs with nearly 20 other women. Upon hearing the embarrassing news, she made another statement: “I deserve a big fat ‘I told you so,’ from everyone.”

A portrait of Jesse James.
Photo by Desiree Navarro/FilmMagic/Getty Images

While Bullock and Von D (and the other nameless women who were cheated on) knew of James’s antics, one woman either didn’t know or chose to ignore it all. And that’s Alexis DeJoria, James’s fourth (and dare I say naive?) wife.

Lucky Number Four: Alexis DeJoria

In late 2012, James proposed to professional drag racer Alexis DeJoria. By spring of 2013, they were married, at her father’s estate. Alexis is the daughter of billionaire John Paul DeJoria (the co-founder of Paul Mitchell hair care products and Patron Spirits Company).

Jesse James and Alexis DeJoria are watching the Annual Summit Racing in Las Vegas.
Photo by Matt Bolt/Icon Sportswire/Corbis/Icon Sportswire/Getty Images

The union made James a stepfather to DeJoria’s teenaged daughter Isabella, which was pretty nice for his own teenaged daughter Sunny, who was living with him at the time. James and DeJoria met in late 2012 at a race after being introduced by her father.

It Was Perfect in the Beginning

Two months later, James proposed, and they were wed by March 2013. At first, the couple was madly in love. They were excited about their future together. Speaking about her in an interview with in 2017, he said this time was a “different deal” – they like the same stuff, the same music, “the same everything.”

Jesse James and Alexis DeJoria are attending a snowed-themed family event.
Photo by Mike Windle/WireImage/Getty Images

Either way, by the spring of 2020, the two separated after seven years of marriage. Like Von D’s explanation for their split, James said his and DeJoria’s lives “were just headed in different directions.”

She Wasn’t So Lucky in the End

James went behind DeJoria’s back with at least 20 women, leaving his seven-year marriage in shambles. He reportedly scoured dating sites for casual hookups and used Snapchat, Instagram, Voxer and Facebook to send racy messages begging women for you-know-what.

A headshot of Jesse James.
Photo by Peter Kramer/Getty Images

According to The Daily Mail, James would sneak his mistresses into his home in Austin, Texas, while his wife – in this case, DeJoria – was away on race meets or at family functions. There were other women who would fly into Austin and hook up with the ladies’ man in hotel rooms.

Their Marriage Turned Toxic

Apparently, James would get aggressive when confronted by DeJoria, who said he was “mentally and emotionally abusive” and turned their marriage “toxic,” according to a close friend of hers. This friend told The Daily Mail that DeJoria felt humiliated and disrespected.

Alexia DeJoria and Jesse James appear during a launch party event.
Photo by Gary Miller/FilmMagic/Getty Images

She stated: “Jesse has been cheating on her since they first met, it never stopped; she’s only now realizing just how bad it was.” DeJoria tried to save the marriage, but James allegedly wasn’t interested – he never came clean. When The Daily Mail reached out to him for his response, he declined to comment.

His Facebook Post Infuriated Her

When James announced their split in March 2020, he posted a lengthy statement on his Instagram profile along with photos from their rosier days of marriage. He said in his post that working on DeJoria’s race car for five of their seven years together was one of the highlights of his life.

Alexis DeJoria prepares for the opening round during the NHRA Nationals.
Photo by Will Lester/Icon Sportswire/Getty Images

According to DeJoria’s friend, James’s public statement infuriated his estranged wife. Claiming that they split because they were going “in different directions” instead of telling the truth was beyond frustrating for the woman who, in reality, had had enough of his infidelity.

In Their Own Bed!

DeJoria had to discover that her husband was not just sleeping with other women, but doing it in her bed. It was devastating and something she couldn’t just put behind her. The 43-year-old racer discovered his infidelity three years ago; he just relentlessly denied it.

Alexis DeJoria takes a photo next to Jesse James while sitting inside the car.
Source: Instagram /@popeofwelding

Even after a period of marriage counseling, he still refused to open up. DeJoria first grew suspicious when random women would just show up at his gun shop or on social media. Any woman’s radar would start beeping, and DeJoria was no exception. She was definitely suspicious, especially given his history with women.

The Night Before His Proposal!

More embarrassing information came to light when a woman contacted DeJoria in late 2017. The woman, named Debra, told her that James had reached out to her on the dating site Badoo. She revealed that James cheated on her as early as November 2012, which would have been two months after they met.

Jesse James and DeJoria smile at the camera after tiding the knot.
Source: Facebook

Debra had sold a car to James, which he gave to DeJoria. According to Debra, she slept with James the night before he proposed to DeJoria. Messages between James and Debra were released, and the Daily Mail reported that he wanted her to be his “sex slave.” (More details were included, but we can’t really expose them here).

An Exposé of Racy Messages

The man’s womanizing first came to light when a hairstylist named Myla Harris contacted DeJoria’s mother and sister in 2017. Harris showed the DeJoria women numerous screenshots of racy messages she exchanged with James on social media.

Kylie McCollough and DeJoria's mother pose for a photo outside their house.
Kylie McCollough, Jamie Briggs. Source: Instagram /@alexisdejoria

Harris then went ahead and exposed everything to InTouch magazine, claiming that for three months, she and James were messaging each other back and forth, referencing specific illicit meetups. James allegedly invited Harris to his Texas home that he shared with DeJoria. However, Harris never took him up on his offer. Whether or not she purposely got involved with James to unmask his infidelity is not clear.

The Cherry on Top

For the cherry on top, DeJoria was recovering from a fractured hip at the time and was feeling awful as it is. Even worse, the kids were around, too. Eventually, his messages with women usually transferred over to Snapchat. It’s sneaky but smart because messages there tend to disappear after a certain amount of time.

DeJoria takes a photo at home.
Source: Instagram /@alexisdejoria

While most of the time, James’s responses to DeJoria’s accusations were hostile and aggressive, there were times when he was remorseful and would apologize. But his words were empty. Eventually, more women reached out to the drag racer.

DeJoria Did Her Own Sleuthing

Rather than just wait for these mistresses to come to her, DeJoria’s friend explained that DeJoria started doing her own sleuthing online in order to gain more evidence (as if what she already knew wasn’t enough?). One night, James left his computer on in their home office. Obviously, DeJoria went through it.

Alexis DeJoria is talking on the phone next to the car.
Photo by Michael Allio/Icon Sportswire/Getty Images

What she found was worse than she expected. He was inappropriately conversing with at least 30 women, many of them sending him naked photos of themselves. After confronting him at that time and providing him with actual proof, he still denied it.

He Blamed Her

Apparently, all he said at that moment was that he shouldn’t have married a famous drag racer. He told her that he knew she was “too popular” – that too many people knew who she was, and that’s why “all these crazies have come out.”

Alexis DeJoria autographs a poster.
Photo by Jeff Speer/Icon Sportswire/Getty Images

He went so far as to blame DeJoria. (What happened to all those new insights a decade ago, Jesse?) According to Dejoria’s anonymous friend, his philandering was “so prolific” that he even reached out to some of the women he slept with years before. He was talking to the women he was with while he was with Kat Von D.

She Quit Racing for Him

What makes the whole thing even more frustrating for DeJoria is that she quit racing for him! Once their marriage hit the rocks in 2017, she decided to give her husband a second chance and really focus on the marriage, and so she made the difficult decision to quit racing.

A studio portrait of Alexis DeJoria holding a white helmet.
Source: Instagram /@alexisdejoria

She was hoping that if she was home more, it would help make their relationship and family unit better. But James wasn’t on the same page. He continued with his behavior and would repeatedly find his way out of her family get-togethers at the last minute, saying he had work to do.

The Final Boiling Point

According to the anonymous friend/source, James owes his father-in-law $1 million, which was lent to him for establishing his gun company in Austin. In late 2019. DeJoria packed her bags and left, only to take him back soon after.

DeJoria hugs her father after a race / A Christmas Tree inside DeJoria's house.
Source: Instagram /@alexisdejoria

Still, tension was building, and the relationship hit a boiling point five days before Christmas when the couple had a bad fight and James kicked her and her daughter out of their own home. The two were forced to move in with the girl’s father for a few months until they found a permanent situation.

He Doesn’t Think He’s a Sex Addict

When James was in rehab a decade ago, he said that he determined he wasn’t an actual sex addict, at least not in the traditional sense. He explained that he’s not “running around trying to have sex with everyone, and I can’t stop.”

A portrait of Jesse James
Photo by Luca Ghidoni/Getty Images

The way he saw it (at least back then) was that he was doing things to sabotage his life, including extramarital affairs, texting, overworking himself, injuring himself, and simply doing “stupid things.” But he went on to say that not all abuse victims go on to cheat on their wives.

Okay, enough bad talking the guy…

Outlaw Garage Only Lasted One Season

In 2012, James was offered the possibility of doing a reality show on the Discovery Channel about building custom motorcycles. The show was called Outlaw Garage if you remember it, and although it only lasted for one season, he loved it.

A portrait of Jesse James.
Photo by Spencer Weiner/Los Angeles Times/Getty Images

Alongside James was his best friend Hildie Katibah, whom he says was his “pilar in life” for the last 12 years while they were producing Monster Garage and PayUpSucker Productions. In his eyes, the two of them made some amazing TV together, but he gives most of the credit to her.

He Lost a Close Friend

It’s never easy losing a loved one, and Jesse James has to deal with his own loss. Candace Muzny was a NASCAR driver who struggled with drug addiction. She and James were very close, and so when the news of her death came, James was devastated.

A headshot of Candace Muzny after a race.
Photo by Jerry Markland/Getty Images

It was especially difficult for him since he had done his best to help her overcome her addiction (being an addict himself). He addressed the issue and his grief over the loss of his friend in another public post. In it, he encouraged people to reach out for help. (Eye rolls, anyone?)

He’s Got a Granddaughter

One of the biggest milestones in James’s life recently was the birth of his granddaughter – his daughter Chandler’s first child. He announced the great news in a post (of course), asking his fans if they remember the “little blonde girl from Motorcycle Mania?”

Chandler and her baby girl Ginger dressed in a unicorn outfit.
Source: Instagram /@popeofwelding

Well, that little girl grew up and is now a mom. He shared his excitement over being a grandpa, which truly seemed genuine. He said such nice words about his daughter – that she’s “a strong, kind, beautiful woman” and that she’s going to be an amazing mom.