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Before he ever stepped onto a stage, or held the title “Doctor,” Leo Gilling was just a barefoot boy in Oracabessa, St. Mary: curious, determined, and full of dreams that seemed too big for the tenement yard he called home. Today, he’s an accomplished: author, educator, philanthropist, talk show host, and thought leader; one of the most respected voices in the Jamaican diaspora across the United States and Canada.
His memoir, From Shadows to Sunshine: My Jamaican Boyhood, offers a cultural blueprint stitched with proverbs, idioms, folk tales, and timeless Jamaican wisdom. “This book is not just my story; it’s a celebration of resilience and community,” he writes. “May it inspire readers to embrace their journeys and discover sunshine even amidst the shadow.”
What a journey it has been.
After earning his Diploma in Education from Sam Sharpe Teachers’ College in 1982, Dr. Gilling never looked back. He moved to the United States, where he would go on to complete a Bachelor of Business Administration in Accountancy and a Master of Science in Criminal Justice; both from National University in 2020 and 2021, respectively. Most recently, he earned his Ph.D. in Criminology from Keiser University in Florida in 2024.
Dr. Gilling’s academic resume reads like a masterclass in perseverance and reinvention. Beyond degrees, he holds certifications with Allstate as an insurance agent and is licensed in accident, health, life, and variable annuities. Education was always about empowerment. Since 2023, he’s served as an adjunct professor at both: the Jamaica Theological Seminary and Washington Adventist University, where he specializes in: curriculum development, innovative pedagogy, student mentorship, and research integration.
His scholarship is sharp and relevant. In 2021, he published the analytical paper, White Police Officers’ Use of Force on Black Citizens Versus Black Police Officers’ Use of Force on Black Citizens, tackling urgent conversations about: race, power, and policing. His work also appears across platforms like Issuu and Medium, where he offers strategies for building Diaspora Playbooks, detailed models for global engagement and policy change.
Dr. Gilling’s life extends far beyond academia…
A man of deep service, he has sat on the boards of numerous philanthropic organizations including the Partners For Youth Foundation, the Broward Alliance of Caribbean Educators, and the Issa Trust Foundation. He has served in advisory roles for the City of Miramar’s Parks & Recreation department, the Jamaica Diaspora Movement, and the Jamaica Diaspora Education Task Force.
He is the founder of the Sam Sharpe Teachers’ College Past Students’ Association (2004), the Jamaica Diaspora Education Task Force (2013), the Jamaica Diaspora Task Force Action Network (2019), and the Celebrate Awareness Association of California (CILA).
His leadership is often described as visionary and transformational. Gauree Patel, Associate Director of Partnership at the NYC Campaign Finance Board and former colleague at the Clinton Foundation, praised him publicly: “Leo’s accomplishments in coordinating and driving large-scale social change is a testament to his charismatic, authentic, and inclusive leadership style… The network building model developed by Leo served as a template for the Clinton Global Initiative in the Caribbean region.”
In 2025, Dr. Gilling entered another golden era.
His memoir launched on April 2nd, 2025, at Excelsior Community College in Kingston, April 3rd, 2025, at Ritual Restaurant, and April 4th, 2023, at Oracabessa High School. The Canadian launches were equally memorable: April 19th, 2025, at the Knowledge Bookstore in Brampton and April 23rd, 2025, at the Jamaican Consulate in Toronto.
His personal life? Equally radiant.
He recently celebrated his daughter’s graduation from Johns Hopkins University, where she earned her doctorate in nursing practice; a proud, generational full-circle moment. Then, on May 15th, 2025, he married Adaoma Patterson (now Adaoma Gilling) in a heartfelt ceremony in Jamaica. He shared his joy with the world via Facebook: “I wasn’t searching. I wasn’t looking. I just bumped into her, and I realized I liked her the way I always wanted to enjoy a meaningful relationship. Now I feel an inner peace I didn’t know I yearned for.”
When asked about what drives him, Dr. Gilling doesn’t rattle off accolades or degrees. Instead, he leans into legacy, “True confidence is forged when you unapologetically embrace every thread of your story: your heritage, your hardships, your humble beginnings, and even the raw edges of your childhood.”
That’s what makes him a Classic Man. The humility, the roots, and the unwavering commitment to elevate others.
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With a last name that means “Faithful and loyal,” it is no wonder that Paul Junor has become a welcomed addition to the Toronto Caribbean Newspaper Team. Since 1992, Paul has dedicated his life to become what you call a great teacher. Throughout the years, he has formed strong relationships with his students and continues to show them that he cares about them as people. Paul is a warm, accessible, enthusiastic and caring individual who not only makes himself available for his students, but for his community as well.
