This was supposed to be Jose Maria “Chille” DeCastro’s year. Really. He was supposed to be in a much better place in 2023. Instead, he poops in a bucket while living in a former pot dispensary and plotting changes to society for when he’ll be governor… one day.

In our “Chille DeCastro at a Crossroads” series last year, we left off with Jose DeCastro lost in the proverbial wilderness and having to make a serious decision about his future.  After losing his previous studio and making the choice to head to Las Vegas, he was in control of his destiny for the new year. Let’s see how he did and if he was a winner or loser of 2023.

As the year began, DeCastro decided to become a social warrior, defender of the rights of anyone who had made the news. Jacquline “Laney” Hudson, a West Virginia teen killed in a traffic accident in the closing days of 2022, became his first real focal point of the year.

Hudson was killed in Huntington, West Virginia, which is near DeCastro’s previous obsession, Ironton, Ohio. Using his old contacts in the area, she was intoxicated and allegedly playing chicken with cars in the middle of the street when she was struck and killed by an off-duty police officer as she apparently ran in front of his car.

DeCastro pounced on the story, using his contacts within Ironton to put him in touch with the family which eventually led to DeCastro becoming the media mouthpiece for the family without needing to visit the state.

Laney’s family, desperate for justice for their little girl, ignored warnings by many community members of DeCastro’s checkered past and accepted the money DeCastro fundraised in Laney’s name. Their resolve was hardened and DeCastro used the issue to attack police in video after video attempting to gain fame from their misfortune.

As with all of DeCastro’s interests, his attention began to wane quickly as he had to put real effort into keeping up with the family’s needs and as the fundraising efforts dried up. By late spring, DeCastro had a falling out with the family and Laney Hudson became an occasional mention only used to attack police officers.

DeCastro started to act more irrationally than normal starting in the winter and into the spring of 2023. The YouTuber would read about an issue, ignore when the issue actually happened, and then call the local number for the police force in order to complain about the issue.

His actions led to some unintentionally hilarious moments as DeCastro, on more than one directing his audience to call flood and review bomb the wrong location. DeCastro himself again, on more than one occasion, called and threatened the wrong person as he became so upset at the videos he watched on YouTube that he couldn’t be bothered to double check the contact information before taking action.

During the early part of the year, DeCastro also attempted to rebrand himself as a dietary expert, advocating for intermittent fasting. The YouTuber advocated for fasting for 16 and 26 hours “a day” and only eating in one-hour windows.

This dangerous dieting impacted both DeCastro’s physical and mental health during the year. With massive fluctuations in his weight and DeCastro going for days without eating, there were times when DeCastro was incoherent for hours at a time, rambling at his audience while appearing malnourished and sickly.

2023 was also the year when DeCastro turned his attention to fundraising for other creators and personalities on YouTube who ran into legal trouble. At one point, DeCastro was doing so much fundraising that announced that he had filed for and received approval for a 501(c)(3) charitable organization so that any donation made to him would be tax exempt. After announcing it, he immediately forgot about it and never mentioned it again.

Insiders in DeCastro’s camp would eventually reveal that DeCastro had engaged in questionable accounting during his fundraising campaigns. The insiders claimed that while the person he was fundraising for would get most of the money DeCastro raised funds for, they wouldn’t get all of the money from that fundraiser. They would only get up to the amount DeCastro said he was fundraising for, whith the rest going directly to DeCastro’s pocket.

DeCastro’s support of Deboraugh Rodgers carried over into early 2023. The YouTuber had been providing Rodgers with legal advice for most of 2022 and pledged that he would do a monthly fundraiser to reimburse Rodgers for legal fees from her unsuccessful attempt to fight DUI charges in Oklahoma.

Rodgers disappeared from DeCastro’s world after losing her court case in the late spring of 2023. Insiders claimed that DeCastro simply grew tired of holding low-value fundraisers on her behalf and he no longer had an urgent reason to do anything for his once “great friend.”

Jeremiah and Samantha Payne’s spring arrest gave DeCastro a new target for his fundraising efforts. After failing to contact bigger YouTubers such as Lackluster and James Freeman, Payne begged his fans to contact DeCastro when both were arrested for outstanding warrants during a livestream.

DeCastro worked overtime for the Payne family. Fundraising for their bond and was able to get both Samantha and Jeremiah out of jail within a week of their arrests. He even found a local driver to take them to court appearances that week, as both were prohibited from driving, and establishing a growing partnership with the Payne family.

As with everything in DeCastro’s world in 2023, the partnership did not last long. Jeremiah Payne wouldn’t listen to DeCastro’s advice and became frustrated with the lack of response from DeCastro as each week the Payne family needed a new fundraiser to earn $500 for their hotel room or their new legal troubles.

At the end of spring 2023, DeCastro started an on-going fundraiser for a man named Eric Trujillo. Trujillo was described as a fan of DeCastro’s who needed $7000 a new wheelchair. DeCastro held multiple fundraisers towards the goal, pledging that he wouldn’t stop until he earned enough from his viewers to pay for the wheelchair.

While DeCastro was successful in his fundraising efforts, rumors persisted that Trujillo was a DeCastro creation. He ultimately “proved” that Trujillo was “real” by sharing a text message he received from Trujillo asking DeCastro to stop contacting him after DeCastro chastised him for not making public statement thanking DeCastro for his efforts.

In July, DeCastro was contacted by Heather Dollarhide, wife of occasional channel guest Jason Dollarhide. Jason had been arrested after having his bond revoked in Oklahoma and fleeing from police who attempted to apprehend him.

DeCastro initially fundraised for Dollarhide’s bail, but as Dollarhide’s previous bail bondsman rescinded his previous bond for occurring new charges, Dollarhide’s bond surpassed $150,000. Once his bond was rescinded, no other bail bonds companies would touch Dollarhide, who remains in jail to this day.

By late July, Heather Dollarhide suffered another blow as her daughter was removed from her custody by Oklahoma’s child protective services. DeCastro convinced Heather Dollarhide to use the money raised for her husband’s bond to file for divorce and then show that she had no more contact with her husband in order to regain custody of her daughter. Pitching the idea that she could quietly reunite with Jason later on when he was released from prison.

The Dollarhides would disappear from DeCastro’s sphere of influence in mid-September after Heather Dollarhide made several posts on YouTube claiming that DeCastro associate Floyd Wallace sexually assaulted her and a friend at her home when he visited to interview her.

After the Dollarhide debacle, DeCastro began to have problems with his video editor, Collin “Project Constitution” Campbell. DeCastro bought Campbell a MacBook laptop and insisted that his editor learn Adobe Premiere Pro. When Campbell refused, DeCastro hired a new editing team, splitting with Campbell in October.

The split with Campbell wasn’t amicable, however. Campbell briefly deleted DeCastro’s Delete Lawz Clips Reloaded YouTube channel in retaliation for DeCastro’s refusal to pay him severance pay. After initial agreements between the two failed over DeCastro’s continued failure to pay Campbell, Campbell took full control of the T-Spring store Campbell had set up for DeCastro’s use.

With Campbell legally owning the T-Spring store, DeCastro began to obsess over the loss. Leaks of DeCastro’s e-mails by Campbell late in the year showed that DeCastro was now threatening to sue T-Spring should they not grant him ownership to Campbell’s T-Spring account.

We’ll explore DeCastro’s legal setbacks and the state of his merchandise empire in part two of Winners and Losers, tomorrow…