15 Life Decisions Jesse James Probably Regrets

Jesse James is definitely one of the most famous reality TV presenters when it comes to cars. He was one of the originals with Monster Garage, which aired way back, from 2002 to 2006. But even before that, he was already hugely popular, and even had a documentary about him made, thanks to him founding West Coast Choppers in 1992.

We've all made mistakes, and Jesse has been in the spotlight for many, many years. He’s had plenty of wives—some who were more famous than he was—and has made many regretful life decisions when it comes to business, relationships, and breaking the rules.

He’s done some awesome things, but he also has some skeletons in the closet he’d rather people forget. Here are 15 life decisions Jesse James probably regrets.

15 Not Being Into Agricultural Builds

via StangTV

In an attempt to appease more green-oriented viewers, Monster Garage tried to build more environmentally friendly cars for a bit, such as the 1990 Mustang GT that was transformed into a lawnmower on the first episode of the show. Unfortunately, Jesse didn’t back these agricultural developments, as he was always about cool stuff like rocket cars and hitting 200 MPH. The agricultural builds might have helped with viewership a bit.

14 Absence From The Show

via Pinterest

Jesse James might have been the host of the show, but that was about it—he was only the figurehead for Monster Garage. Insider Larry said that he usually didn’t show up to the garage at all, and if he did, it was for about half an hour everyday. There were many times when he was supposed to show up but didn’t. One of the times he didn’t show up it was because he was out racing. He did minimal work on the cars.

13 Monster Garage: The Video Game

via Reddit

If it were up to Jesse James, he would probably nip this one in the bud before it ever got green-lit. The Monster Garage video game was ill-conceived, boring, had bad graphics, and it definitely didn’t help the brand whatsoever. It has dismal ratings across the board from the big video game companies: Gamespot gave it 3.3/10, and IGN gave it 3/10. If he could do it over (and had any say), Jesse James would’ve made sure this product never saw the light of day.

12 Firing An Employee On The Spot


Jesse James was known to have quite a temper on his show (just look at what he did to the failed builds!). He probably regrets firing a Monster Garage employee over an errant comment. At the time, the team member was transforming a DeLorean DMC-12 into a hovercraft, and Jesse got frustrated about the team removing some of the outer bodywork. A crew member disagreed with Jesse, and instead of hashing it out, he fired the team member on the spot.

11 Not Following Rules With California Air Resources Board

via Autoevolution

Anything that costs you money is usually something you’d like to change. Here, Jesse James could have saved himself a lot of hassle, time, and money. When customizing a car, there are strict rules and regulations you must follow, for health and safety reasons. Disregarding these legal boundaries is a big no-no. But Jesse did it anyway, and the California Air Resources Board ended up fining West Coast Choppers for bikes he made between 1997-2006, to the tune of $271,250.

10 Failing To Hit 200 MPH

via DeviantArt

No one likes to fail, least of all someone with the temperament of Jesse James. Throughout Monster Garage’s five seasons, one of Jesse James’ main goals was to create a build that could top 200 mph. The closest he got was with his Toyota “Hellica” build, a Celica rocket car that managed to reach 185 mph. He was satisfied with the build and didn’t destroy it, even though his ultimate aspiration was never reached.

9 Giving Away Builds To Producers

via Screen Rant

Considering how Monster Garage ended, and how Jesse James pretty much got used by the Discovery executives in the end, he’s probably not too happy that some of the builds from the show went to producers from Discovery. Most of the successful, expensive vehicles that weren’t destroyed were taken home by people who had nothing to do with building them in the first place. Jesse would probably rather destroy those builds, if only out of spite.

8 Breaking A Huge Contract

via Popular Mechanics

Jesse James often broke rules during his time on the show, without repercussions, but there was one rule he broke that got him in some pretty hot water. James failed to create a custom order for Michael Jones, despite the fact that he had paid $270,000 over two years for the vehicles. James never got the job done and requested more money, which seems pretty shady. In the end, the two went to court and it was settled privately (allegedly for $422,680 against Jesse), and this is definitely a tarnish on Jesse’s reputation.

7 Denying Sylvester Stallone

via Speed Society

Not only did Jesse James refuse to build a bike for Sylvester Stallone, but the reason for it is absolutely stupid. Apparently, Jesse hated the color yellow so much that when Stallone asked for a custom bike in that color, Jesse refused to make it. It’s not every day that an A-list celebrity gets turned down over a disagreement about color! I guess it shows that Jesse James has morals and rules he stands by, even if they’re wacky.

6 Fighting With Discovery Channel

via YouTube/Graham Bensinger

Jesse James didn’t only fight with producers of the show, but he also fought with Discovery Channel once his second show was cut. He let his emotions get the better of him and destroyed the long-term partnership he had with Discovery over Outlaw Garage. He put up a blog post saying, “For all those asking about Outlaw Garage, I’m sorry to say that I’m done with Discovery. It’s time to take skills and hard work to a network that appreciates what I offer…”

5 Claiming Outlaw Connections

via National Geographic

This has gotten Jesse James into some hot water, as well as having his reputation and honesty questioned. He claims that his great-great-grandfather was the cousin of the outlaw Jesse James, but many people aren’t so sure. Eric James, the president of the James Preservation Trust, says he couldn’t find any record of Jesse on the family tree. He asked Jesse to provide a DNA sample, but the TV presenter refused, prompting Eric James to call him a fraud.

4 Marrying Janine Lindemulder

via Daily Mail

Jesse James probably regrets this life decision simply because it ended poorly, in a breakup. Janine Lindemulder was his second wife, whom he married the same year he split with his wife (which led to rumors of infidelity). Even though the two had a daughter together, Lindemulder ended up in prison for tax evasion. The adult actress tried to regain full guardianship of their daughter after she served her time, but Jesse fought hard in court and kept custody, giving Janine weekly visitation rights.

3 Cheating On Sandra Bullock

via HotCars

It’s always difficult when a celebrity marries another celebrity, especially one who is so much more famous. Such was the case with Jesse James and Sandra Bullock, the hugely popular actress. The pair married in 2005, just a year after his breakup with his previous wife. But Jesse couldn’t stay faithful to his superstar wife, and they were divorced in 2010. That’s probably something he regrets, big time!

2 Relationship With Kat Von D

via CBS News

Jesse James began dating another really popular star in 2010, the tattoo artist Kat Von D. By 2011, they had announced their engagement, but then they called it off by the summer of that year. A month later, the engagement was back on, but then a month after that it was off again. Kat Von D said she couldn’t stay with Jesse because he had allegedly been unfaithful to her several times during their relationship.

1 Getting In Trouble With Fortune Fashions

via The Star Beacon

Jesse James has been in a number of legal battles: against his ex-wives, against the California Air Resources Board, against clients, Discovery Channel, etc. In 2010, he was in another legal battle, this time when Fortune Fashion Industries LLC claimed he stole one of their executives to work on a project with Walmart. They wanted over $6 million in damages, claiming he had stolen their idea and manpower. Jesse’s lawyer pointed out he was an entrepreneur and had many successful ventures like this one, and eventually, the courts ruled in Jesse’s favor.

References: monagiza.com, imdb.com, gamespot.com, caranddriver.com

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