Meet Trisha Bailey, The Richest Jamaican-born Woman

Dr. Trisha M. Bailey, a Jamaican-born multimillionaire and University of Connecticut (UConn) graduate, made history in 2022 when the university revealed she had “committed a significant lead gift” to contribute with the development of a state-of-the-art student-athlete center.

Bailey’s gift, according to UConn, “represents the largest cash contribution ever received from a UConn alumnus, and the largest gift dedicated specifically to UConn Athletics.” The sum donated by Bailey, however, was not disclosed.

Bailey, a member of UConn’s cross country and track & field teams and a member of the 1999 graduating class, was born in Jamaica. She comes from a low-income family and grew up in a Caribbean country without power or running water. She moved to the United States with her sister when she was 13 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 living in the United States was easier for her than in Jamaica, she was subjected to sexual abuse by her stepfather not long after arriving. Oprah Winfrey’s 1993 autobiography helped her get through what she called “hell at home.”

“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.”

Despite the challenges she faced at home, Bailey attended college and worked as a stockbroker on Wall Street before becoming a pharmaceutical sales representative. During this time, she faced trauma from multiple abusive relationships that she kept hidden from friends and family.

She remembered waking up after being in a coma for eight days after a relationship with a man in Los Angeles. Following that incident, she was confined to a wheelchair. She was inspired to launch Bailey’s Medical Equipment and Supplies after a stranger assisted her in making a connecting flight home to Florida from the hospital in Los Angeles.

Bailey’s Medical Equipment and goods, founded in 2011, distributes medical goods to Medicare patients. Bailey has grown her medical supplies business in Florida into an empire, with 46 pharmacies spread across multiple states. Bailey’s Scrubs, Bailey’s Real Estate, Bailey’s Ideal Choice Homes International Real Estate Division, Bailey Charitable Foundation, and Serenity Ranch are among the 15 businesses he founded.

Bailey is also a half-owner of an island in her home country of Jamaica. She plans to build a resort on the site. Her Florida equestrian farm is also said to be the largest in the state. She has also donated over $10 million to charitable causes in the Orlando region.

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

“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.

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