Earl Leroy Bailey

Earl Leroy Bailey, Sr. passed away on April 16th. His legacy is one of love, strength, faith, and unwavering presence. He will live on through his family, through the lives he impacted, and through the countless stories that will continue to be shared about the man he was. He will never be forgotten, and his family will continue to tell the world about his life, his love, and the profound difference he made in the lives of so many.

Earl Leroy Bailey, Sr. was born on July 12, 1955, in San Nicolas, Aruba. He spent his earliest years there before moving to St. Kitts, where he was raised and spent much of his childhood. At the age of 13, Earl moved to New York City to join his mother, a transition that marked the beginning of a life defined by resilience, faith, and deep connection to others. In New York, Earl attended Lehman High School in the Bronx and began building the community that would anchor him throughout his life. At The Greater Refuge Temple Church in Harlem, he found both spiritual grounding and a sense of belonging. He joined the choir and men’s ministry, and it was there that he met his future wife, Donna Cartwright. Their love grew from a shared faith and devotion, forming a partnership rooted in loyalty, strength, and care.

Earl attended Lehman College for two years while nurturing his relationship with Donna, traveling regularly between the Bronx and Queens, an early reflection of the intention and commitment he brought to the people he loved. At 26, Earl and Donna were married and began their life together in the Bronx, where they welcomed their three children, Earl Jr., Jasmine, and Janay. They later moved to New Rochelle, New York, where they raised their children into adulthood and built a home filled with love, structure, and unwavering support. Throughout his life, Earl carried a strong and steady work ethic. He held positions at Barclay’s Bank, IBM, and Weil & Gotshal, later serving as a landlord before becoming a dedicated billings coordinator at Loeb & Loeb. In every role, he was known not just for his diligence, but for his integrity and the quiet way he supported those around him.

Earl was a man of deep faith, one of the most faithful a person could encounter. He believed wholeheartedly in God’s word and lived that belief daily, not only teaching his children to trust in God’s principles, but demonstrating love, compassion, and grace through his actions until his very last day. To know Earl was to feel grounded. He had a calming presence that allowed people to fully be themselves, an emotionally safe, judgment free space where anyone could speak openly and be met with understanding. He was empathetic, intuitive, and deeply generous, always showing up for others in moments that mattered most. Whether through a timely phone call just to say, “I’m just checking on you,” or by offering words of encouragement that gave someone strength to keep going, Earl had a gift for reaching people exactly when they needed it. He often reminded those he loved, “You have to be mentally strong,” a reflection of the resilience he carried and instilled in others. His generosity was boundless, often giving more than what was asked, simply because he wanted to make sure those around him were cared for.

Earl found joy in life’s simple and meaningful pleasures. He loved grocery shopping at health food stores, carefully selecting high quality foods, supplements, and superfoods. He also took pride in making powerful, nutrient rich juices for himself and his family, another way he expressed his care and commitment to their well being. He cherished memories of his childhood in the Caribbean, often sharing stories of picking fresh fruit from trees and the ease and beauty of life there. He was also a loyal New York Knicks fan who loved basketball, having played in his youth and later sharing that passion with his grandchildren. Known for his strength and discipline, he could still impress with his push ups and pull ups, a quiet testament to his lifelong commitment to health and vitality. Above all, Earl was a devoted and loving father, and an incredibly proud and present “Pa.” His love for his children and grandchildren, was immeasurable. He cherished every moment with them, pouring into their lives with the same care, wisdom, and joy that defined him.

Earl is survived by his beloved wife, Donna Bailey; his children, Earl Jr., Jasmine, and Janay; his cherished grandchildren, Cairo, Harper Kaelan, Kaia, Nadir, and Nala; his siblings, Andeline, Joseph, Hubert Sr., and Ronald; nephews and nieces, Anita, Nigel, Sandra, Justin, Julian, Keith, Mario, Hubert Jr., Danielle, Somari, Samora, Yani, Jasent, Tamika, Shatiaya and Adrian, and a large extended family, including grand nieces, grand nephews, godchildren, and friends, whose lives he touched deeply.

Earl Leroy Bailey, Sr. passed away on April 16th. His legacy is one of love, strength, faith, and unwavering presence. He will live on through his family, through the lives he impacted, and through the countless stories that will continue to be shared about the man he was. He will never be forgotten, and his family will continue to tell the world about his life, his love, and the profound difference he made in the lives of so many.

A Celebration of Earl's life will be held at the Pelham Funeral Home located at 64 Lincoln Avenue, Pelham New York on Friday April 24, 2026 between the hours of 4:00 pm and 8:00 pm. Interment will take place on Saturday April 25 at 11:45 am at Greenwood Union Cemetery, located at 215 North St, Rye NY 10580

For more information or to leave a condolence please visit www.pelhamfuneral.com.