Meet the Wealthiest Woman in Jamaica, Dr. Trisha Bailey: Empire-Builder, Billionaire and Healer

Source: National CARES / National CARES

“Trisha Bailey’s story was a best-kept secret of transformation and out-sized achievement until her breathtaking autobiography and our acknowledgment of her at our National CARES gala brought her journey from a painful past of abuse to track star to billionaire entrepreneur into the spotlight,” Susan L. Taylor, Founder and CEO of CARES, and Editor-in-Chief Emerita of Essence Magazine,  told NewsOne during an exclusive interview.

NewsOne’s commitment to spotlighting Black women who have made significant strides in music, media, and business has us shining a light on Dr. Trisha Bailey, Founder and CEO of the renowned Bailey’s Pharmacy and Bailey’s Medical Supplies & Equipment.

Bailey, a University of Connecticut graduate and track star, whose illustrious career spans over two decades in the medical industry, launched her groundbreaking companies Bailey’s Pharmacy and Bailey’s Medical Supplies & Equipment, in 2011, dedicated to offering compassionate care to the elderly and disabled. The company works with assisted living facilities, Medicare patients and contract facilities, providing top knot medical supplies. 

Bailey with Susan L. Taylor Source: National CARES / National CARES

“With a heart to provide care from the least to the greatest, we touch the lives of many in our community through employee volunteering, a courteous attitude, and concern for our clients. In return, we receive the satisfaction of knowing what it means to be a part of a great cause,” Bailey’s company website states. 

Dr. Bailey’s portfolio encompassed 16 thriving enterprises and her flagship company employs over 500 people and boasts revenue in the hundreds of millions. Business Insider noted that the St. Elizabeth Parish, Jamaica native’s networth stands at a towering $1 billion, and her accolades include the groundbreaking distinction of being the first Black person to have a building named after her at the University of Connecticut for making the single largest contribution to the school’s athletic department—a place that had been life-saving for her.

But to locate the remarkableness of Bailey solely in her successful business empire, is to miss the learning and compassion that came with her battle to succeed. Bailey’s climb to the top came with some terrible challenges and setbacks, some that wound all the back to her childhood. Bailey was abused as a teenager and grappled with domestic violence as an adult. She’d been traumatized, but as highlighted by NBC News,  her trauma did not stop her from moving consistently to the place where she could hold her dreams with both arms tightly.  

Following her college years, Bailey embarked on a career trajectory that led her to Wall Street as a stockbroker at Salomon Smith Barney and subsequently transitioned into the pharmaceutical industry as a sales representative.

A Coma Led to her Breakthrough

In 2010, Bailey went into a coma for eight days  following an encounter with a man she was on a date with in L.A. The tragic experience left her wheel-chair bound, with a clipped larynx, impairing her ability to speak.

Once discharged from the hospital, Bailey headed to Florida to heal, a trip that required her make a connecting flight in Atlanta. Sitting alone at the gate in a wheelchair waiting for someone to help her board the aircraft, Bailey felt totally “invisible.” The harshness of the experience led to the birth of her medical company. 

“When I got to Atlanta,” Bailey recalls, “the flight attendant escorted me off the aircraft, placed me in a corner for my connecting flight for two hours. I sat there and I cried and tried to find someone to help me to get to my next destination. After two hours, a young girl came and helped me, and during that moment, I realized that the disabled were invisible to the world and because of that, I started Bailey’s medical equipment and supplies,” she explained in a video shared to her company website. 

“I wanted no one else in the world to ever feel the way that I did as a young girl sitting there in a wheelchair, crying, desperately needing help, needing someone to care, needing someone to assist me.”

Despite facing adversity, Bailey’s company has flourished exponentially. Beyond her expansive network of 46 pharmacies spanning multiple states, she has spearheaded the establishment of 15 additional enterprises. Her global real estate holdings and diverse investments, including stakes in prominent sports franchises like the Atlanta Hawks, Charlotte Hornets, and Phoenix Suns, underscore her multifaceted ventures. More, her philanthropic endeavors have left an indelible mark, with significant donations, including an undisclosed sum to UConn athletics, heralded as the largest in the institution’s history.

In effort to drive focus on the issue of abuse prevention and neglect, Bailey’s Pharmacy and Bailey’s Medical Supplies & Equipment collaborates with organizations like Castle, offering educational resources and support to victims. Additionally, she courageously shared her tumultuous upbringing and abuse narrative in her poignant memoir, UNBROKEN: The Triumphant Story of a Woman’s Journey, aiming to heal from her past traumas and inspire those who may feel trapped by their circumstances to envision a future of success beyond their pain.

Bailey is a North Star Award Honoree.

In February, Bailey received the esteemed North Star Award at the annual For the Love of Our Children Gala, bestowed by the National Cares Mentoring Movement for her unwavering dedication to support Black children living driving change in the medical industry sphere and her advocacy for those affected by abuse.

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A post shared by Dr. Trisha Bailey (@creatingmyownyes)

“Trisha’s candor, embracing shadows most would shun, her grace, and a boundless wellspring of affection, tenderly unbinds souls. Enamored, hearts entwine in her luminous wake,” she continued. 

“I so admire that Trisha is a beacon guiding a way forward—echoing the conscious-shifting, healing programmatics the National CARES Mentoring Movement is rooting in our neglected communities. Trisha, too, has tended to her own mending, made it paramount, has become the architect of her desires, harnessing the alchemy of thought and action, as CARES teaches, to build the life of abundance and mutuality God created us to live.”

See More:

For Many Black Women, Entrepreneurship Presents A Path To Liberation

Women’s History Month: The Unique Challenges Faced By Black Women In The Fight For Equality

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