Winston Stewart, the fourth child of Stanley and Phylis Stewart, was born on November 16, 1941, in Grove Place, Manchester, Jamaica. Growing up, he enjoyed playing cricket and driving his father’s car. He also spent many hours tending to his father's farm and livestock, developing a strong work ethic that would define his character throughout his life.

In the early 1960s, Winston began training as an Auto detailing mechanic. However, he quickly realized this was not his calling, stating, “I did it at the insistence of my father; but I really hated the job and the work environment.” In 1964, he seized an opportunity for a change, becoming a Porter at the Jamaica Railway Corporation (JRC), Mile Gully station. Three years later, in 1967, he briefly worked as a Motor Trolley Apprentice Driver/Operator for the same company.

That same year, Winston married his beloved Beverly Stewart, and they soon began raising their family. Together, they had six children—Robert, Elvis, Winston (Jr), Courtney, Marsha, and Christopher—who primarily grew up in Clarendon. In 1969, Winston transitioned to the role of Locomotive Driver, a position he held diligently for the next 35 years.

In 1982, his wife Beverly became a Jehovah’s Witness. While Winston did not fully embrace the faith, he always supported his wife’s religious beliefs and her efforts to instill those principles in their children.

Winston was a devoted father who consistently went above and beyond for his children, often sacrificing his own needs so they could eat. He worked long hours, frequently at night, and while he slept during the day, everyone had to be extremely careful not to wake him.

Winston embodied the essential qualities of a family man, provider, and disciplinarian. He believed that virtues such as honesty, dedication, and tenacity were crucial for his children to navigate the world, and he instilled these qualities in them from a very young age. Winston also had a strong inclination for perfection, especially regarding maintaining a certain code of behavior, completing his various projects around the house, or simple chores like cleaning shoes, making beds, or cleaning up after dinner. These tasks had to meet his approval, or they would be repeated until he was satisfied with the outcome.

Winston possessed a larger-than-life perspective, believing no task was too big or too small for him to handle. As a result, he gained a reputation within the community as a jack of all trades. Despite economic challenges, Winston led his life with a strong sense of independence, fortitude, and personal pride.

Shortly before his retirement in early 2004, Winston’s health began to decline, and he was diagnosed with a serious heart condition that, at the time, carried a prognosis of imminent fatality. Through unwavering faith, resilience, and determination, Winston defied these odds, taking radical steps to extend his life by seeking medical treatment in the U.S.A. In 2011, Winston migrated to California, USA, where he faced another health setback when he was diagnosed with COPD.

Despite numerous challenges in the succeeding years, Winston maintained a positive and hopeful outlook, undeterred by his circumstances. In 2018, Winston made one of the most significant decisions of his life by dedicating himself to Jehovah. He was baptized that same year and spent the remainder of his life as a dedicated servant of Jehovah.

As his heart condition worsened, other complications compounded his overall health, inevitably leading to his passing on May 26, 2025, at approximately 4:24 a.m.

Winston will be remembered for his infectious smile, his caring spirit, and the love he showed to his children, grandchildren, great-grandchildren, friends, and family. He enjoyed cooking and loved sharing his specialty, Chicken Chop-Suey, with anyone who would accept. He also found joy in playing dominoes and Rummikub, often for hours if given the opportunity.

His family extends their heartfelt gratitude for the love, support, and prayers received during Winston’s transition.

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