Herbert Randall Wright III, better known as G Herbo, was born and raised in Chicago, deeply influenced by the tough environment around him. Speaking on the No Jumper podcast, he opened up about his reality:
“I was in the streets. I knew I could either die or go to jail every time I left the house. But in my mind, I didn’t want that for myself. I saw myself as more than just that.”
Music became his way out. By 2018, a freestyle and several tracks catapulted him into the spotlight. Since then, he’s dropped seven studio albums, including a collaborative project with Southside, solidifying his place in the rap game.
But despite his success, G Herbo’s life has been far from smooth. He’s continued to wrestle with the challenges of his past while living out two of the messiest relationships the internet has ever seen.
Before anyone starts calling us “stanky, single, Big Bone haters” for diving into Herbo’s business, let’s give it up for Auntie Regina to lighten the mood:
“I still got to eat my snacks. Yeah, I’m eating with it. I’m still eating with it. I’mma munch on this!”
Now, back to the story. To understand the rollercoaster of G Herbo’s love life, we need to rewind to 2014 or 2015, when he started dating Ari Fletcher. The couple welcomed their son, Yoson Santana, in April 2018.
Three months later, G Herbo appeared on Angela Yee’s Lip Service podcast, where he spoke candidly about their relationship:
“Man… all my girl wants to do is fight, Swervo. You gotta deescalate situations. She’s cool, but she’s crazy.”
It wasn’t surprising when their relationship ended shortly after Yoson was born. Ari, who was dealing with postpartum depression, took to social media in October 2018 to announce the breakup, accusing Herbo of being a “hoe.”
And that’s just the beginning of the drama. Stick around as we dig deeper into G Herbo’s personal life and how he balances fame, family, and the challenges that come with both.
“Herbo the Hoe… I kinda like that. We broke up because he’s just like all the others. He wants to be out here doing his thing… but you’re not gonna do me like that. Honestly, the only reason I’m not even going off is because, at the end of the day, that’s my son’s dad. Unfortunately.”
But Ari wasn’t done yet. She took to social media again to make it clear she was single. Then, she shared a screenshot of Herbo FaceTiming another woman, allegedly, while his friend was recording him. Ari captioned it:
“Wrap it up, sis.”
In other words, she was implying that Herbo was seeing someone questionable.
The online detectives went to work trying to figure out who Herbo was FaceTiming. They eventually figured out that the other woman was Taina Williams, the daughter of former reality star Emily Bustamante and stepdaughter of rapper Fabolous.
Naturally, people flooded Taina’s Instagram, calling her a homewrecker.
Herbo jumped into the conversation with a post of his own:
“LOL, y’all trippin’. I’ve been single before any of y’all even knew what was going on. Y’all need to stop with the internet, it’s frying y’all brains.”
Okay, but what’s frying? Your pants? We need to know what’s really going on down there, huh? Behind your zipper? Talk about frying…
Weeks later, 23-year-old Herbo was seen hanging out with 20-year-old Taina in the studio. Ari, clearly feeling some type of way, expressed her feelings online. After Herbo posted a photo of their son, Ari commented:
“You haven’t called him in over a week. Don’t post my son.”
Others told her to move on, but Herbo and Taina kept doing their thing, celebrating his birthday. Taina even gifted him a chain with a pendant of his late grandmother’s face, which brought him to tears.
But none of that phased Ari. She went back on social media to accuse Herbo of having herpes. She also claimed Taina had slept with Herbo’s close friend, rapper Lil Bibby. Ari wrote:
“The Lil Bibby? She’s a cumrag-ass wannabe wifey-ass hoe. Herb, you have herpes, and that’s something you’re going to die with.”
She also accused him of using witchcraft to try and rid himself of his supposed herpes (though, let’s be real, that doesn’t seem to work like that).
Around this time, Ari met rapper Moneybagg Yo. If you want the full details of their relationship, check out the video linked in the description box. He said:
“I’m going to get her what she wants, man, before she leaves me.”
Ari replied:
“I’m not going to leave you.”
Herbo and Taina’s relationship continued to grow, and eventually, Herbo met her stepdad, Fabolous. Fabolous gave him his approval, saying on WGCI radio:
“She always spoke of him in a good light, and when he came around, he was exactly who she said he was.”
Because both men were in the same industry, Fabolous felt the need to give them some relationship advice (though, honestly, I’m not sure I’d take relationship advice from Fabolous).
In December 2019, Herbo’s friend and collaborator, Juice WRLD, tragically passed away from an accidental overdose at the age of 21.
A few months later, in February 2020, Herbo released his album PTSD. In the song “Feelings,” he rapped about his co-parenting situation with Ari:
“These the years now when he young, but my jit watching
Just ‘cause we fell out of love, that ain’t his problem
Every kid want a mommy and a poppy
But how we gonna co-parent when it’s sloppy?”
In his interview with The Breakfast Club, Herbo also shared how he struggled with addiction. He revealed that he started using Percocet and lean at 15 and battled addiction for years. Eventually, he went to therapy and checked into detox centers twice. He said his son was the main reason he decided to get clean, though he still faced scary moments, like waking up unable to breathe or sweating excessively. Taina stayed by his side through it all, even though she never told her parents the full story about his addiction.
As of his February 2020 interview, Herbo claimed he had kicked the habit. He surprised Taina with a new G-Wagon for her birthday in April 2020.
Later that month, during an appearance on Angela Yee’s Service Podcast, Herbo gave more insight into his relationship with Taina. He explained that when they had arguments, he would talk to her mom:
“Something Tyena probably wouldn’t understand, because she’s emotional or angry. When I try to explain it to her, I go to her mom. She can relay it to Tyena from a whole different perspective.”
“You’re not in a relationship with her mom; you’re in a relationship with her. And if you two can’t communicate, that’s a problem.”
Herbo also explained that both Emily (Fabolous’ partner) and Tyena’s biological father trusted him to take care of her. They knew she was in good hands whenever she was with him.
When the rumors about him cheating on Ari with Tyena started to swirl, Herbo shut them down during an interview with Angela Yee, making it clear that they were false—and that Ari knew the truth.
Fast forward to November 2020, when Ari stirred the pot once again on social media. She asked a photographer to take down a picture of Tyena holding her son.
Herbo, not holding back, said, “She’s always trying to get pictures removed. This chick is crazy as hell.”
When a fan asked why she wanted the photo deleted, Ari responded, “I don’t want my son in public with her holding him because she told me herself that ‘your son does not like her.’ I don’t want him to be uncomfortable.”
Later that day, Herbo took to social media, posting, “Happy hoes ain’t hating.”
Ari didn’t hold back and fired back with a message on her Instagram Story: “How they got a cure for COVID and not herpes? Fix it, Black.”
In December 2020, Herbo found himself facing serious trouble, slapped with federal fraud charges. He and eight others were accused of using dark web sites to steal credit card info, allegedly spending it on luxury vacations, private jets, and designer puppies over a span of four years.
Herbo’s lawyer requested permission for him to travel to New Jersey to see Taina, who he referred to as Herbo’s pregnant fiancée. Despite facing up to 20 years in prison, Herbo pled guilty, was sentenced to three years of probation, and had to pay a hefty amount in restitution.
In May 2021, Taina gave birth to their son, Essex. While she was focused on their new baby, Herbo was spotted at Ari’s birthday party in July 2021. Social media fans quickly noticed that Taina had unfollowed Herbo on Instagram.
The Shade Room posted the news, prompting Taina to comment: “That’s still my man. He just blocked. Nothing to see here.”
Later that month, Herbo hinted in an interview with Streets 94.5 that he was planning to get married soon. Whether he was serious or not was anyone’s guess.
Soon after, Herbo and Taina announced they were expecting baby number two. Ari, not one to stay quiet, took to the internet and shared a troubling story: “Tell them how my son came home with a scar and said what Taina did to him while you weren’t home. He told you what happened, was crying, and she didn’t help him. She’s mean to him, and he doesn’t like her.”
Taina shot back, denying the claims: “I’ve let you create false stories about me before, but not when it comes to a child I care about so much. I’ve always had to hide my love for your son out of respect for you.”
Ari responded by sharing a recording of her son recounting what happened, telling Taina to stop pretending to be a saint. “Been not liked you. Ain’t gonna like you. Tried again, and you blew it.”
In May 2022, Herbo and Taina welcomed a baby girl, Emmy, making Herbo a father of three. But just a month later, Herbo was caught sliding into an Instagram model’s DMs, sparking rumors of another fling.
Taina wasn’t ready to let go. During a September 2022 Instagram Live, she and Herbo reflected on the early days of their relationship. Fans quickly noticed the overlap in the timeline of their romance and Herbo’s relationship with Ari.
Taina responded to accusations that she had been involved with Herbo while he was still with Ari by saying:
“Lies, lies, and lies. I’m tired of y’all making up stories and creating your own timelines.”
But just three months later, during an interview on Caresha Please, Herbo came clean. He admitted he did, in fact, cheat on Ari with Taina. And to make matters worse, he confessed that he’d also cheated on Taina with other women.
“Did you cheat on Ari with Taina?”
“Yeah.”
No wonder Ari had been so upset. Naturally, Herbo and Taina’s relationship eventually ended. By June 2023, he confirmed the split by posting “single” on his Instagram Story.
But as things go, they gave it another try. In April 2024, Herbo surprised Taina for her 26th birthday with not one, but two luxury cars—a Rolls-Royce and a Range Rover. The big question remained: Did he buy them with a stolen credit card?
A couple of months later, rumors began to swirl again after Herbo was seen hanging out with WNBA player Angel Reese. Meanwhile, Taina shared a video of herself lip-syncing to Sexy Red’s “Pound Town.”
The internet had a field day, with people saying it was karma for Taina, who had been involved with Herbo while he was still with Ari.
As it stands now, Taina and Herbo appear to be done. Ari is also reportedly facing relationship issues with Moneybagg Yo. Fans have been hoping that Herbo and Ari will reconnect, convinced there are still lingering feelings between them.
At this point, maybe it’s time for all parties to take a step back from the drama and focus on themselves—for their kids’ sake and their own.
As for us here at RRG, we’ll just sit back, grab some snacks, mind our business, and continue watching this wild story unfold from a distance.
If you enjoyed this video, drop a comment below, and thanks for watching RRG.
Amen.
When you really think about it, life would be so much easier without all the drama that comes with relationships, dating, cheating, and social media mess. Imagine how much you could focus on your career, your health, building something new, or just reconnecting with the friends and family you’ve been neglecting. Heck, you could even pick up a book.