Dr Trisha Bailey To Receive Luminary Award at 29th Annual Caribbean American Heritage Awards

Dr Trisha Bailey of Jamaica

Institute of Caribbean Studies

Release Date

Friday, October 28, 2022


Dr Trisha Bailey, the Jamaican-born entrepreneur, philanthropist and public speaker has been selected to be honored with the Luminary Award at the 29th Annual Caribbean American Heritage (CARAH) Awards. Life for many entrepreneurs has not been a crystal stair, and for Dr. Trisha Bailey, there is no exception. Her gritty background makes her no stranger to hard work, but it is her passion and kindness that have led to her success, making her the wealthiest Jamaican woman to this date. 

Trisha Bailey migrated to the United States from Jamaica, leaving behind a family, hoping and praying for her success. While many people may view her past as dark and traumatic, Trisha Bailey has taken those experiences to help create her own yes by strategically facing the obstacles in her journey head on. She graduated college with her bachelor’s degree from Connecticut in 1999, where she lit the track as a star athlete. She would then attain a master’s degree in business administration in 2005 and a doctorate in management in organizational leadership in 2010. Dr. Bailey has taken over the home medical equipment industry as the only black woman in this arena, establishing pharmaceutical and durable medical equipment facilities across the country. In 2021, she was nominated for HME (Home Medical Equipment) Woman of the Year! An award recognizing woman globally for their leadership in the market. Additionally, Trisha’s company, Bailey’s Medical Equipment & Supplies, placed as a finalist in the HME awards.

Dr. Bailey has dominated the real estate market, owning half of an island and a plethora of commercial and residential real estate properties stretching from the United States to Jamaica. She is the first Black woman to own commercial real estate in the prestigious town of Vero Beach and Edgewood, Florida. Her business acumen and decision-making skills have placed her on the track to becoming one of the few women entrepreneurs to become a billionaire and change the course of history. Recently, the University of Connecticut bestowed the student body with a state-of-the-art facility named after Trisha Bailey— the Bailey’s Student Athlete Success Center (Draft concept of the building is seen below). Naming the building after Dr. Bailey is an honor that allows Dr. Bailey to humbly reflect on the hard work, accomplishments, dedication, and the passion she has poured into herself and others. This momentum experience resulted in Dr. Bailey becoming the first black person to be honored with a building on the campus of the University of Connecticut.

Dr Trisha Bailey

Dr. Bailey’s profession has given her the opportunity for intellectual stimulation, emotional fulfillment, and competence development, all while assisting individuals and advancing her business. However, it is her love for her children that genuinely drives her philanthropic philosophy and vibrant personality. That love bleeds into how she handles people from all walks of life, giving her a sense of belonging and purpose. Through the Bailey-Archie’s Charitable Foundation, Dr. Bailey has helped boost the graduation rate by nearly 50% at a local high school in Orlando, FL. Furthermore, her contribution to programs that service single mothers, supply weekly food drives, and provides scholarships has significantly impacted the lives of many in her community. For Dr. Bailey, the feeling of giving back is unparalleled to anything she possesses because she genuinely believes that life’s true significance is determined by what you give rather than what you receive. She is impacting society and the world in many ways and for the better.

The CARAH Awards is presented by the Institute of Caribbean Studies (ICS), the leading Caribbean-American advocacy organization responsible for securing Presidential Proclamation of June as National Caribbean American Heritage Month. The prestigious honors recognize the contributions and accomplishments of Caribbean leaders in various fields while celebrating Caribbean pride and the great promise of Caribbean immigrants to America and the world.

The 29th staging of the CARAH Awards will return to its in-person format this year at the JW Marriott in Washington DC on Friday, November 18, 2022.  In 2020 and 2021, the CARAH Awards were held virtually as the world grappled with the novel coronavirus.



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