Raymond Cobbler

August 14, 1949 - August 21, 2026

Raymond Kenneth Cobbler was a loving and supportive husband, a devoted father and grandfather, a dedicated postal worker, a union representative, and a military veteran.

Raymond was born on August 14, 1949, on the island of St. Vincent to Keitha Henrietta Pitt and Wilberforce Cobbler. He lived there for the first several years of his life before his family moved to Trinidad and Tobago, where his father sought greater employment opportunities. It was there that Raymond first met Dianne Quamina. Their paths crossed several times, but a relationship would not blossom until years later.

Raymond spent his youth developing into a young man with a strong work ethic, a deep sense of duty, and an adventurous spirit. He worked in the shipyards and served as a cadet in the civil service. During the political unrest that swept Trinidad and Tobago around 1970, Raymond also played a role in the response to an attempted military uprising that threatened the government.

The 1960s and early 1970s were a transformative and tumultuous period throughout the Caribbean. Trinidad and Tobago gained its independence from Britain in 1962, and the young nation faced the political, social, and economic challenges of establishing its own future. Like many young Caribbean men and women of the broader postwar migration era, Raymond eventually set his sights on North America in search of opportunity and a future of his own making.

With only $20 in hand, Raymond made his way as far north as Canada, where he rejoined friends from his hometown and others he had made along the way. He eventually moved to Brooklyn, New York, where he and Dianne's paths crossed again. Still, their moment had not yet arrived.

In October 1971, Raymond joined the United States Army, serving on active duty during the closing years of the Vietnam War and attaining the rank of Specialist Four (SP4). Trained in infantry and indirect-fire operations, he earned the National Defense Service Medal and qualified as a Sharpshooter with both the M-16 rifle and .45-caliber pistol, as well as a Marksman with the hand grenade. After approximately two years of active service, Raymond was honorably transferred to the U.S. Army Reserve to complete his military obligation. His service to his adopted country reflected the discipline, duty, and commitment that would characterize his life and thus became part of his journey toward becoming a citizen of the United States.

Raymond returned to Brooklyn, where he attended Medgar Evers College. He later married Dianne, and together they built a family and raised three children. As a provider, Raymond worked a variety of jobs before beginning what would become a long career with the United States Postal Service.

Raymond eventually moved his family to Florida, where he continued his career with the Postal Service and became a union representative, a role he would hold throughout the remainder of his postal career. He received numerous commendations for his work and service to others, including recognition for performing lifesaving procedures that helped revive an incapacitated colleague.

After 30 years, Raymond retired from the United States Postal Service. Shortly thereafter, he returned to work as a school crossing guard for the City of Margate. Several years later, Raymond finally entered full retirement.

Through every chapter of his life, Raymond remained a devoted husband, father, and grandfather. He loved and supported his wife, his children, and his grandchildren with the same sense of duty and determination that had defined his life. Though he faced numerous health challenges, Raymond met them courageously, without self-pity, and with the unrelenting love and support of his family.

On August 21, 2026, Raymond Kenneth Cobbler concluded his earthly assignment and proceeded to Heaven to receive his new set of orders. He leaves behind a legacy forged through courage, hard work, service, sacrifice, and devotion to family.

Raymond was preceded in death by his son, Tesfa Kenneth Cobbler, who passed away in August 2021.

Raymond is survived by his beloved wife, Dianne; his daughter, Renee; his son, Sheldon; his daughters-in-law, Tamara and Christina; his son-in-law, Darrell; his grandchildren, Ebony, Markus, Mackenzie, Aidan, Justin, William, and Layla; and the multitude of friends and loved ones whose lives were forever shaped by his presence.

Visitation will be held at Bailey Memorial, 6701 West Commercial Blvd, Tamarac, FL 33319, US, on September 12, 2026, from 11:00 am to 12:00 pm.

A Funeral Service will be held at Bailey Memorial, 6701 West Commercial Blvd, Tamarac, FL 33319, US, on September 12, 2026, from 12:00 pm to 2:00 pm.