Guilty plea puts Chicago rapper G Herbo on path to prison – Chicago Tribune

After surviving the gritty streets of the South Side neighborhood dubbed “Terror Town,” Chicago rapper G Herbo’s career was starting to take off in 2017 when he released a video for his hit song “Man Now,” filmed at an exotic villa in Jamaica.

“You know I come from a city of sorrow,” the then-22-year-old Herbo rapped at the song’s outset, along with dramatic shots of palm trees, infinity pools and an oceanside gazebo. “Ugly introduction, red snow, heartaches, heartbreaks, headaches.”

Herbo would later tell an interviewer the song was one of his favorites because it told a personal story about overcoming myriad obstacles in his poverty-stricken neighborhood “and, most importantly, never going back.”

“Something that was destined for me in my life took me along a path to Jamaica, vacationing in a multimillion dollar estate,” Herbo said in the interview with The Fader magazine.

Now, six years later, Herbo’s path appears to be headed to federal prison. And that Jamaican villa is Exhibit A.

On Friday, in a small courthouse in western Massachusetts some 900 miles from his hometown, Herbo, whose real name is Herbert Wright III, admitted he participated in a scheme to use stolen identities to fund private jets, swanky hotel rooms, “designer puppies,” and the six-bedroom island estate where “Man Now” was filmed.

Wright’s guilty plea comes more than 2 ½ years after the Tribune first reported he had been indicted on charges of conspiracy to commit wire fraud and aggravated identity theft. A charge of lying to agents was added in a separate indictment in 2021.

The more serious wire fraud count carries up to 20 years in prison, but under federal sentencing guidelines Wright would likely face a term in the two- to three-year range, calculations that were still being worked out as of Friday.

Wright’s attorneys have also reserved the right to argue for probation under the terms of the deal. U.S. District Judge Mark Mastroianni set a sentencing hearing for Nov. 7.

In a written statement Friday, Acting U.S. Attorney Joshua S. Levy said Wright “flaunted his lavish spending on social media, in music videos and in industry news,” and that his conviction “should serve as a reminder that if you break the law, you will be prosecuted and held accountable – regardless of who you are.”

Wright’s attorney, James Lawson, did not immediately return calls or emails seeking comment.

The guilty plea capped a tumultuous three years for Wright, whose indictment in October 2020 came as his fame was skyrocketing, with performances on the “Tonight Show” with Jimmy Fallon, collaborations with stars such as Nicki Minaj and Chance the Rapper, and an appearance on Forbes’ “30 under 30″ musicians list.

Wright vehemently denied wrongdoing at the time he was charged, even dropping a new song and video in late 2020 that mocked the federal investigation and touted his rise from troubled South Side streets to international acclaim.

“Ask about me, I ain’t never been a fraud,” he said in the two-minute video titled “Statement.” “I worked hard from the start, in my city I’m a god, (expletive).”

But behind the scenes, Wright’s attorneys were negotiating a resolution short of trial. Court records show the plea deal was first proposed earlier this year and was signed by Wright on June 5.

Weeks later, Wright was arrested in Chicago after police pulled over a Cadillac Escalade the star lyricist had been riding in and allegedly found four guns in the car, including a black Glock 33 pistol in the center console that was “uncased, loaded, and immediately accessible,” according to the police report.

Wright was charged with misdemeanor unlawful use of a weapon following the July 9 arrest and bonded out of police custody a day later. The case is up for a preliminary hearing next week.

Whether Wright’s legal troubles and possible imprisonment will dent his still-robust career remains to be seen, but either way his rise from Terror Town has been remarkable.

Wright’s youth, as described in his blunt lyrics, was spent dodging bullets and hanging out on the violent streets near 79th Street and Essex Avenue. But as his star rose and money rolled in, Wright said he started to realize it was time to move on from his past and embrace his newfound fame.

“Honestly I’m just trying to capitalize and build other people up,” Wright told the Tribune in a 2019 interview. “I’m a firm believer that life is what you make it. … I been broke so many times. I was supposed to be dead. I was supposed to be in jail. But I’m still here.”

But even as Wright’s fame rose, the relentless gun violence in Chicago, which he often raps about, continued to affect those close to him.

In February 2021, a few months after Wright’s indictment, one of his close associates was killed in a brazen daytime shooting in a South Loop barbershop.

Police said Gregory Jackson III, 24, better known as “Lil Greg,” was in Studio Nineteen when a man walked in and asked for directions to the restroom. When he came out moments later, the man pulled out a handgun and fired several shots to Jackson’s head. No one has been charged.

The indictment brought in U.S. District Court in Springfield, Massachusetts, charged Wright and several others, including his longtime promoter Antonio Strong, with using stolen identities to make hundreds of thousands of dollars in fraudulent charges for goods and services.

Strong bought and traded the illicit account information, which they referred to as “moves,” on the dark web, though there was no indication Wright was involved in that aspect of the scheme, the plea stated.

In his plea agreement, Wright admitted that he “used the proceeds from these frauds to travel to various concert venues and to advance his career by posting photographs and/or videos of himself on the private jets, in the exotic cars and at the Jamaican villa.”

The plea agreement contained numerous text messages and chat logs between Wright and Strong, including one where Wright called Chicago “the Raq” — a shortened version of “Chi-raq” — and allegedly asked Strong to “finesse” him a hotel room, meaning to obtain one through fraudulent means.

“I’m in the Raq. See if you could get me sum for tonight like to check in when I leave for my show tonight,” Wright texted to Strong on July 30, 2016, according to the plea. “Finesse me a room or sum dude get us a crib while we out here or sum bro.”

Wright also admitted in the plea agreement to conspiring to fraudulently charge more than $80,000 in private jet flights in 2017. On one flight from Tampa Bay to Chicago in March 2017, Wright was listed on the passenger log as “Herbert Light,” the plea stated.

Wright and five companions “posted photographs and videos from the private jet,” and Wright used footage from the plane in a music video for his song “Yerky’s,” the plea stated.

The video, still available on YouTube, showed Wright and several others in his entourage dancing in the plane’s cabin and on the tarmac, as he raps lyrics such as, “Don’t show no remorse or sorrow, like I’m a demon. I put money over everything, and I really mean it.”

The flight cost $20,679, which Strong paid for using an electronically signed credit card authorization that turned out to be stolen. After the victim disputed the charge, the airline rental company, ASG, was denied payment, according to the plea.

Three months after that flight, Wright texted Strong an image of the six-bedroom Hanover Grange villa in Jamaica and told him via text message, “I need to you get this,” according to the plea.

Wright wound up traveling there for six days in July 2017, with a guest list of eight associates, according to the plea. The $14,600 reservation was charged to a credit card that was later flagged as a fraudulent transaction when the actual cardholder disputed the charge, the plea stated.

But perhaps the most bizarre aspect of the scheme came later that year, when Strong and Wright allegedly conspired to purchase the puppies from Woof Woof Puppies in Southfield, Michigan.

According to the plea, Strong, using the name “Darren Geiger” and identifying himself as Wright’s manager, ordered the dogs for Wright using a stolen credit card.

The pet company appeared to be suspicious and asked for Wright to confirm the order by messaging it directly from his Instagram account, according to the agreement. Strong allegedly sent a text to Wright saying, “Hurry just message that (expletive) hello.”

The indictment alleged Wright did what he was told. The company representative messaged Wright back on Instagram, asking, “You are getting 2 puppies correct?” Wright then confirmed the order, according to the charges.

The puppies were delivered, but the deal apparently soured after the payment was reversed due to suspected fraud.

According to the plea agreement, on Dec. 6, 2017, Wright sent Strong a text message relating to the Woof Woof fraud, saying, “I already finessed these dogs for you & didn’t give no (expletive)… you sold at least one what you did wit the bread ain’t my problem.”

Two months later, one of the Woof Woof owners threatened Wright via a direct message chat, saying they would go to the police if he didn’t resolve it, according to the plea document.

“We have you in the photo, witnesses, license plate. This is a felony,” the Woof Woof owner wrote, according to the plea.

Wright allegedly responded: “Don’t you see the pictures on my page??? Does that look like me in that pic?? I never met you.”

The Woof Woof owner replied that Wright had messaged directly from his Instagram page while they were on the phone, and “the phone call was recorded.”

“All of this is going to the local police,” the owner said. “They will investigate. You messaging from your official Instagram page shows you were getting 2 puppies. What are you gonna say?? That’s not you??”

Wright never responded further, and the dogs were never paid for, according to the plea.

Under the terms of the plea agreement, Wright will pay $140,000 in restitution to a variety of alleged victims, including $10,458 to Woof Woof.

jmeisner@chicagotribune.com