Da Baddest & Da Realest: Rapper Trina Talks About Her ‘Dark’ Days After Devastating Losses Of Mother, Brother & A Baby

Hip-hop legend Trina has faced unimaginable loss throughout her journey to stardom and Da Realest is bravely detailing it all.

In her new memoir, Da Baddest, which dropped on Oct. 8, the Miami native candidly shares the highs and lows of her career, including a heartbreaking miscarriage and the profound losses of her mother and brother.

During her appearance on The Tamron Hall Show on Oct.16, Trina discussed an audio excerpt from the book, revealing that she felt “like a failure” after experiencing a miscarriage while dating fellow rap star Lil Wayne from 2005 to 2006.

The 45-year-old opened up about the overwhelming sense of “emptiness” she felt, which made it challenging for her to grieve properly amid her demanding work schedule.

“There was no time to have a slumber party with friends and just cry,” the “Look Back at Me” hitmaker told Hall on Tuesday’s show. “I would cry on the road, I would cry on the tour bus, I would cry in a hotel, but I would have to hit the stage that night. I would have to get on a plane that morning, I would have to do whatever I was doing. It was something that you kind of like swept under the rug. I was so young and I was just, I was hurt. I was sad inside. I just [started] questioning things that I believe in and why me. You know, I didn’t understand. Like, was it something that I did wrong? Like, why? I blame myself so much for it.”

This isn’t the first time Trina has opened up about pregnancy loss. Back in 2023 during an episode of her “niece” Yung Miami’s “Caresha, Please” podcast, she shared that she actually suffered three miscarriages.

“Well after three miscarriages, I would’ve had three kids,” said Trina. “The first one was — I don’t think I understood it too much [because] I was younger,” said Trina. “Then once I got older, there was the next one I was like ‘Okay, what does that mean? What does the miscarriage mean?’ Like I just didn’t really get it.”

Trina Said Life Went “Dark” When She Lost Her Brother And Mother

On Tamron Hall, Trina shared that she was hesitant to talk about her miscarriage while at the peak of her career, fearing it would derail her success.

Rather than confront her pain, she buried herself in work until the 2013 death of her brother, Wilbrent Bain, compelled her to pause and process her grief. Bain was reportedly shot and killed following an argument, according to NBC Miami.

“The loss of my brother is when life went dark for me,” Trina shared. The rapper went on to lose her mother, Vernessa ‘Nessa’ Taylor, in 2019 due to cancer, according to TMZ.

“I really stopped believing in everything that I believe in life. Like I just felt like God, ‘what are you doing? Why is this me?,” Trina said as tears streamed down her face. “I just started breaking down. I don’t understand how do you live without your mom? Like my mom is the person I call every second of the day… and this person is no longer here.”

She added;

“If my back was against the wall, my mom was always there. She’s never not been there for me. When she wasn’t here, I just felt alone in the world.”

Trina expressed her gratitude to her husband, Benjamin Leon Kearse Jr., for supporting her during her darkest days, helping her to feel “whole” and “alive” again. Their romance blossomed around the same time she faced the tragic loss of her niece in 2022.

“When I met Ben, he replaced a lot of the pain and made me feel fulfilled. He poured into me,” Trina said with a big smile.

Trina and her husband tied the knot in May.

Watch the full clip of Trina’s appearance on The Tamron Hall Show below.

Hit the flip for more from Da Baddest as she continues detailing her new book.