Tekashi 6ix9ine Excited For Jail After Donald Trump's Venezuela Operation

Tekashi 6ix9ine is oddly excited about jail, and Donald Trump has something to do with it.

The rapper resumed jail with very ambitious aspirations to spend quality time with the recently arrested Venezuelan President, Nicolás Maduro, who is in the same facility.

Tekashi's 6ix9ine jail trip comes after he experienced a home invasion by four armed men, who held her mother captive, although in his absence.

Inside Tekashi 6ix9ine's Jail Plans

Rapper Tekashi 6ix9ine reports to serve his 3-month sentence for violating his supervised release. He will spend time in the same prison as Luigi Mangione and Nicolás Maduro. pic.twitter.com/gpHQK6XrnF

— Chuckyfamous! (@Nem_Famous) January 6, 2026

The rapper checked into jail on Tuesday afternoon in a sprinter van, with his songs blasting over the speakers. According to him, his three-month stay in jail will give him proximity to Maduro, who is in the same building.

He voiced his intention to dance with the arrested dictator and would take it a step further by challenging him to a game of cards. Tekashi will be residing at The Metropolitan Detention Center in Brooklyn, New York, for the next three months.

Aside from Maduro's presence in the facility, the controversial Luigi Mangione also calls the place home, and Tekashi plans to inform the inmate about all the love he has gained on the outside.

Although Tekashi does not support the death of United Healthcare CEO Brian Thompson, TMZ reported that he stated that he does not think Mangione is a bad guy.

Donald Trump's Raid In Venezuela Affected Some Hollywood Stars

While the president swarmed in on Maduro and his cohorts, celebrities who landed in cities across South America for a time out experienced a sudden hitch in their flights. 

As shared by The Blast, Trump's move caused the entire airspace across South America to shut down, causing Hollywood's famous faces to get trapped in St. Barths and the surrounding beaches.

Several celebrities, including Queen Latifah, Mike Tyson, Ming Lee Simmons, Natalie Portman, and Richie Akiva, reportedly got caught in the debacle. The restriction affected several commercial and private flights, which are at the mercy of the decision to lift the grounding of flights.

While some celebrities tried taking boats to neighboring islands with hopes to fly from there, sources claimed that they were sent back. On the bright side, Leonardo DiCaprio reportedly made it out just in time to attend the 2026 Critics Choice Awards.

Tekashi 6ix9ine Was Stripped Down By Law Enforcement In Early 2025

Perhaps not so similar, but the rapper had his fair share of police invading his territory last March when they executed a search warrant in his Florida home. According to The Blast, the raid was carried out by the federal U.S. Probation officers, assisted by Palm Beach Sheriff's Office Narcotics Investigators.

The sheriffs described the raid as a probation check where several items, including firearms and drugs, were confiscated and carted away for further analysis. Tekashi claimed that the cops kept him in handcuffs for hours while the raid went on, although officers later established he was handcuffed for safety reasons.

He added that DNA samples were also taken, and they wanted to see if his DNA was on the guns and drugs seized from the location. The rapper stressed that he never did anything wrong or criminal and was merely relaxing in his home while on house arrest.

The 29-Year-Old Violated Terms Of His Release Last Year

Takashi earned his freedom from jail in 2020 following his incarceration in 2019 due to charges accusing him of participating in violence with the gang known as Nine Trey Gangsta Bloods. He was promptly sentenced to two years in prison, but claimed his health was threatened due to the rapid spread of the pandemic behind bars.

He was then released to go home and obey a court-supervised release alongside probation. In October 2024, he was then seized in New York for violating the terms of his 2020 release following his conviction for a felony in 2019.

The rapper's probation officer had complained about him failing multiple drug tests and flouting rules about getting permission to travel out of the country.

Tekashi has had a rough past with the law in past years, including a child sexual performance charge in 2015 following released clips of him filming a friend having sex with a minor.

He was also investigated over the shooting of Chief Keef and was taken into custody in the Dominican Republic for multiple alleged incidents.

Tekashi 6ix9ine's Mother Was Forcefully Seized During Home Break-In

Tekashi 6ix9ine Begins 90-Day Jail Sentence in Brooklyn

We shall miss the new song rappers from him 🙂 pic.twitter.com/w3mTSqxhtR

— KYTON (@kyton_allan) January 6, 2026

The 29-year-old experienced a shocking event last November after four men broke into his Florida home and left a very concerning sight on the surveillance camera. In the clip, Tekashi's mother is seen getting grabbed by one of the men, while three other men proceed with the operation.

The footage reportedly showed the burglars tearing down the apartment while searching for valuables like money and car keys. Tekashi was away from the scene, getting super busy on a live-stream with influencer Jack Doherty while officers from the Palm Beach Sheriff's Office were dispatched to the home.

Unfortunately, the burglars escaped by the time officers from the office arrived with a special K-9 unit squad. In the same month, he came under heavy scrutiny from internet users after he mocked Demi Lovato's sobriety journey, claiming that she would relapse.

Looks like Tekashi 6ix9ine will do just fine behind bars!