For Immediate Release
September 05, 2023
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Curtis Bunn

(BPRW) Meet the entrepreneur who faced abuse and poverty before becoming the richest Jamaican-born woman

Trisha Bailey’s memoir, “Unbroken,” tells how maintaining grace in the face of trauma launched her to unimaginable wealth and joy.

(Black PR Wire) In the last decade, Trisha Bailey has turned a small medical supply business in Orlando, Florida, into an empire that stretches across seven states. From her years as an athlete at the University of Connecticut to her reported net worth of at least $700 million, Bailey’s success story is magnified by the tumultuous route she traveled. 

To her many achievements, including being the wealthiest Jamaican-born woman ever, the 46-year-old entrepreneur just added the release of a memoir, “Unbroken: The Triumphant Story of a Woman’s Journey,” in which she shares the darkest parts of her life boldly and poignantly. At a recent book signing in Martha’s Vineyard, many were moved to tears when she discussed passages of her book and her trauma-filled youth and adulthood.

Bailey grew up in an impoverished home in St. Elizabeth Parish, Jamaica. As a teenager she survived sexual abuse and then, as an adult, domestic violence.

At the book signing, Bailey was emotional right along with her readers as they poured over her story. She had shared the traumas of her life with only a select few — until now. And although she said writing the book was not therapeutic for her, it was revelatory. 

“The life of trauma that I was going through, I didn’t know other people didn’t live like that,” Bailey said. The more she shared about it, however, the more she learned differently, which is why she aimed for transparency. 

“There were so many different incidents that happened, and I was like, ‘No, that’s so embarrassing. Maybe I shouldn’t share that,” Bailey said. “But I said, ‘You know what? If I’m going to help others, I need to just tell it all.’”

She did. Bailey wrote that, at 13, just a few days after arriving in the U.S. from Jamaica, her life took a traumatic turn.

As she “was going through hell at home,” Bailey said that she found Oprah Winfrey’s 1993 autobiography. “I saw that she was able to overcome,” she said. “I was able to see this woman on TV and it gave me life. She gave me hope. And I wanted to be able to touch other young women to show them what to look for, to show them how to build themselves up.”

One could assume that Bailey’s ability to succeed despite intense trauma is what makes her book so enticing. Another could point to her success as an entrepreneur that has earned her phenomenal wealth. Neither would be wrong.

After college, Bailey became a stockbroker on Wall Street and later a pharmaceutical sales representative. All the while, she endured difficult relationships that she shielded from most family and friends.

Bailey wrote about waking up after being in a coma for eight days about 13 years ago. She could not remember what led to the near-death experience, but her last memories were of an encounter with a man she was dating while visiting Los Angeles.

When she was able to leave the hospital in L.A., she found herself disoriented in an airport while seeking a connecting flight home to Florida.

Finally, a stranger came along and aided Bailey to her gate. As harrowing as those moments were, she said they sparked an idea that would be crucial in her business journey. While sitting in a wheelchair provided by an airline, she said, she conceived Bailey’s Medical Equipment and Supplies, which launched in 2011 to distribute medical supplies to Medicare patients. 

Since then, Bailey’s empire has grown exponentially. In addition to her 46 pharmacies in multiple states, she has founded 15 companies, owns real estate around the globe and has stakes in the Atlanta Hawks, Charlotte Hornets and Phoenix Suns, among other endeavors. And she has donated millions, including an undisclosed amount to UConn athletics that the school says is the largest in its history.

“I know that my business success is not normal,” Bailey said. “I know it is a blessing from God, like my entire life. But having grace and being kind and caring and loving blesses your business. If you’re someone who’s doing the wrong things, morally corrupt, your business may miss being blessed because God is in the middle of all those things.”

Even as Bailey, a mother of five, works her various enterprises and myriad philanthropic efforts with a bright resolve, her book is a reminder of the tumult she had to overcome.

She wrote in “Unbroken” about one instance when a man choked her: “I admit, there was a sudden realization that I could die, and the more I fought back, the more the thought became real … so much so that I almost took comfort in the idea of death because I couldn’t take this anymore. I just wanted it to be over. Then, I began to imagine what the better version of myself would have wanted me to do. Fight!”

Rhoan Stewart, who has been Bailey’s friend since she was a 22-year-old broker at investment firm Salomon Smith Barney (now Morgan Stanley), said he was flooded with various emotions as he digested Bailey’s story.

“When I read her book, I was very, very angry,” he said. “Tears came to my eyes. I couldn’t sleep for two days. It was painful. Finally, I called her and she said, ‘Rhoan, I’m good. I’m good.’ She kept saying that. But it’s hard for us to know that she has gone through this suffering and pain and abuse. How can you be good after that?”

 Bailey attributes much of her progress to therapy, particularly Eye Movement Desensitization and Reprocessing, a process in which patients recall traumatic images in order to move past previous events.

“I was able to release the hurt from the trauma,” Bailey said. “I was able to forgive all the people who had done me wrong. It has given me life.”

Kathy Jackson, Bailey’s closest friend since their days at UConn, said Bailey’s joy was evident when they met during Bailey’s freshman year as track teammates. The turmoil she endured pained her, but Bailey’s spirituality never faded, Jackson said. As an illustration of her caring, she pointed to her friend’s contributions of more than $10 million to charitable organizations in Florida alone.

“That’s my favorite part of the book, Chapter 15,” Jackson said, “It shows who she really is — a loving, kind person all about family despite all she’s been through.”

For Bailey, who will begin a book tour in September, the journey has produced more than she could have imagined. 

“I am truly the happiest I’ve ever been,” she said. “I didn't even know people could be this happy, to be honest.”