How Trisha Bailey overcame trauma to hold the title of richest Jamaican-born woman

In 2022, Jamaican-born multimillionaire and University of Connecticut (UConn) graduate Dr. Trisha M. Bailey made history at her alma mater after the university announced she had “committed a significant lead gift” to aid the construction of a state-of-the-art student-athlete center.

UConn said Bailey’s donation “represents the largest cash contribution ever received from a UConn alumnus, and the largest gift dedicated specifically to UConn Athletics.” The amount Bailey donated was, however, not revealed.

Bailey, who was a member of UConn’s cross country and track & field teams and part of the graduating class of 1999, was born in Jamaica. She comes from a modest background, growing up in the Caribbean nation with no access to electricity or water. When she was 13, she relocated to the United States with her sister to join their mother and stepfather.

“It was a better life,” Bailey said. “Even though we were in these apartment buildings that are as low-income as you can imagine — we lived in a one-bedroom apartment, and my sister and I slept on the pullout sofa — for me, it was, ‘OK, I have electricity, I don’t have to go outside to use the bathroom.’ I was in luxury land. I didn’t know at the time that we were not rich.”

Even though life in the U.S. was easier for her than in Jamaica, she experienced sexual trauma from her stepfather not too long after her arrival in the States. What helped her to get through what she described as “hell at home” was Oprah Winfrey’s 1993 autobiography. 

“I saw that she was able to overcome,” she said of Winfrey, according to NBC News. “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.”

Indeed, despite the difficulties she went through at home, Bailey went to college and started work as a stockbroker on Wall Street before becoming a pharmaceutical sales representative. She experienced trauma again during this period from several abusive relationships she hid from friends and family.

She recalled once waking up after being in a coma for eight days following a relationship she had with a man in Los Angeles. She was wheelchair-bound following that incident. After a stranger had helped her make a connecting flight home to Florida from the hospital in Los Angeles, she was inspired to start Bailey’s Medical Equipment and Supplies.

Launched in 2011, Bailey’s Medical Equipment and Supplies distributes medical supplies to Medicare patients. Today, Bailey has turned her medical supply business in Florida into an empire, with 46 pharmacies in several states. The 46-year-old is also behind 15 companies including Bailey’s Scrubs, Bailey’s Real Estate, Bailey’s Ideal Choice Homes International Real Estate Division, Bailey Charitable Foundation, and Serenity Ranch.

Bailey is also the half-owner of an island that is situated around her native Jamaica. She intends to construct a resort on that property. Her equestrian farm in Florida is also reported to be the largest in the state. And she has donated over $10 million to charity-related endeavors in the Orlando area.

With a net worth estimated to be between $650 million and $700 million, NBC recognizes her as the richest Jamaican-born woman.

“I know that my business success is not normal,” said Bailey, who credits therapy to her success. “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.”

The mother of five with an MBA and Ph.D. in organizational leadership recently released a memoir, “Unbroken: The Triumphant Story of a Woman’s Journey,” which shares her story.