Weston Diggs Profile Photo

Weston Diggs

1937 - 2026

Weston Cornelius Diggs Jr. was born on September 23, 1937, in Chicago, Illinois, to parents Weston Cornelius Diggs Sr. and Edna Mae (Tillery) Diggs. In 1939, the couple gave birth to another son named John, who, unfortunately, as a toddler, died of pneumonia at just 18 months old. In the early 1940's, Weston Sr. decided to move his family to Detroit, Michigan, where most of his paternal family resided. He soon began working for his younger brother, State Senator Charles C. Diggs Sr., founder of The House of Diggs Funeral Home. During this transition period, Weston Jr. would attend Lincoln Elementary School. And after school let out, he would routinely hurry home to help his dad and his Uncle Charles at the funeral home. His parents divorced in 1946 when young Weston Jr. was almost 9 years of age. After the divorce, Edna moved back to Chicago with her son, where most of her family resided. But she would customarily arrange for Weston Jr. to visit his father back in Detroit and to stay with him for the entire summer. Sometimes, letting him stay the entire school year, where he would attend Hutchins Intermediate School in Detroit. Weston Jr. would then go back to Chicago for the summer with his mother and stay the entire school year in Chicago. This sharing of custody went on for about 5 years, and Weston Jr. would later admit that he enjoyed commuting between the two cities and schools. He always felt loved and accepted in both places. Although Edna was granted legal custody of Weston Jr., she would eventually allow him to permanently stay with his dad back in Detroit, where he would continue to help out his dad and uncle at the Diggs Funeral Home. Weston Jr. would then go on to attend Cass Technical High School. He was later recruited onto the Cass Tech varsity basketball team in just his sophomore year, earning himself a varsity letter. He also received a varsity letter in track and field. But it was with basketball and playing on the team's starting five, where Weston Jr. would make his biggest impression at the school. His team would go on to win 27 games with only a single loss for the season. Ultimately, winning the highly coveted and prestigious city championship in 1955.

Weston Sr. was very proud of his son and his accomplishments in basketball. More so after learning his son was offered a basketball scholarship at Albion Liberal Arts College in Michigan. But Weston Sr. strongly dismissed any ideas of his son playing basketball in college and told Weston Jr., "No basketball". I would rather you attend Howard University. So Weston Jr. honored his father's wishes and would eventually attend Howard University in January 1956. Later admitting that he had the best time of his life in the years he was a student there. Making a lifetime of friends and meeting many interesting people along the way. As an elevator operator in the Old Capitol building, he had the pleasure of meeting and talking with Senators Hubert Humphrey and George McGovern, as well as Attorney General Robert Kennedy and Congressman Adam Clayton Powell Jr. And as the Treasurer of the Young Democrats of the District of Columbia he had the honor of sitting next to and chatting with Eleanor Roosevelt, at a dinner in her honor. But nothing could compare to or even be anticipated by Weston Jr. than what would soon change his life forever. And it would all happen outside of the boundaries of Washington, D.C. and Howard University campus life. In 1959, after returning home to Detroit from Washington, D.C., for Thanksgiving break, Weston Jr. met his future wife, Kay Jackson. They were introduced at a house party hosted by their mutual friend. Their first meeting was so successful that they exchanged phone numbers before the night was over. Since Weston Jr. had to return to Howard University in Washington, D.C., their courtship centered around many, many months of long-distance phone calls. But on that rare occasion that he came back to Detroit, the two would get together and go out on dates. Their courtship and friendship grew, and in April 1960, he proposed to her, and she accepted.

On February 11, 1961, Weston Diggs Jr. and Kay Jackson were married at 4619 Georgia Ave NW, Washington, DC. Their wedding was at the home of Diggs' family friend Ramona Jones. The couple were married by Reverend Page, who was an ordained clergy member from the AME Zion Church, the same church that Ramona's father, Bishop Raymond Jones, supervised. Newly married and anxious to start a family, the couple wanted to chart a course that ensured that they would become financially independent. Weston Jr. had already been working at the Old House office building as an elevator operator across from the U.S. Capitol, which paid pretty good money. But Weston Jr. needed to get Kay working also, so he got his new wife a new job (through a faculty member friend at the college), as a clerical secretary in Howard's administration office. It was the perfect job for Kay since she had already been honing and perfecting her typing and shorthand skills while attending Commerce High School in Detroit. Connected to Cass Tech High School, it was known for its specialized training with a focus on business education and secretarial skills. After having both secured jobs and less than one year after they tied the knot, the couple would welcome their first child, Weston III. Born on January 28, 1962, at Historic Freedman's Hospital, located on Howard's campus. Their second child, Annette, arrived on September 7, 1963. During this time, Weston Jr. was already in his first year of law school, and the couple was starting to feel the financial pressures after Weston Jr. lost his well-paying elevator operator's job. So in late September, just two weeks after Annette was born, Weston Jr. courageously suspended his law school studies. His cousin, Congressmen Charles C. Diggs Jr, drove the Detroit funeral home station wagon to Weston Jr. and his family in DC. And Weston Jr. drove the family back in it to Detroit. After several months of soul searching and job searching, Weston Jr. decided that it would be best to join his family in the House of Diggs funeral business and make a career of it. So, in June 1964, Weston Jr. enrolled in Wayne State University's Mortuary School of Science. He graduated a year later in 1965. He then went on to pass the Michigan State Board of Examiners. As he was now fully licensed, Weston Jr. was then officially welcomed to the family funeral business by cousins James P. Diggs and Congressman Charles C. Diggs Jr. A news release by the Michigan Chronicle pictured the three of them side by side. At an early age, young Weston Jr. was always surrounded by his uncle Charles' thriving family funeral business. And as fate would have it, he would finally become a licensed funeral director and once again start working for his family. Weston Jr. would eventually become Managing Director of The House of Diggs Southwest Chapel. In the meantime, his wife Kay started her career in her preferred profession with secretarial work at GM's Fisher Body Plant. She would eventually move up the ranks and land an upper-echelon job within the company as a secretary to executives. Relocating her to the internationally renowned General Motors headquarters building on W Grand Boulevard. As things were looking up for Weston Jr. and Kay, the couple purchased their first home in 1965 at 18631 Roselawn in NW Detroit.

In 1977, Weston Jr. left behind the family funeral home business and embarked on an entirely new career path within the healthcare HMO sphere. This career move could be considered risky at the time since HMO's were relatively new. It was only officially signed into law by President Richard Nixon in 1973. Weston Jr. started as a marketing representative in September 1977 with the now-defunct HMO Group Health Plan (GHP). But soon his risky career move began to pay off. His hard work resulted in him receiving numerous sales awards. As his burgeoning skills in Marketing and sales grew, many Group Health Plan competitors began actively seeking out Weston Jr. for employment, as the HMO industry continued to grow. And after only 10 years of service with GHP, he moved on to Health Alliance Plan (HAP) in 1988. Along the way, Weston Jr. received many sales leader and above the call of duty awards from HAP throughout his distinguished 12-year career with the company. But most noteworthy is what sets Weston Jr. apart from his peers in the HMO business. It was the day when William Lucas, Michigan's first black sheriff, personally presented to him the Office of Wayne County Commission Community Services Award. It's an award that honors individuals for their outstanding service to the community. Weston Jr continued to serve HAP and the community with virtue and greatness until his retirement in 2000.

On April 2, 1982, Weston Jr. and Kay welcomed their third child, Anthony, "Tony". And not much longer after Tony's birth, the couple moved into a spacious home in the quiet upper-middle-class neighborhood of Farmington Hills, Michigan. It was their third home together. Also, around this time, Weston Jr. would purchase his first boat. At first, settling for a 25ft 1981 offshore Bayliner. And after a year had passed, he decided to sell it and purchase a 36ft 1968 Uniflite Sports Sedan boat. Family and friends really enjoyed the time spent on that boat. Weston Jr. even had it docked at a cozy and quiet marina in neighboring Windsor, Canada. It was a nice getaway from city life.

In 1991, Weston Jr. and Kay divorced after 30 years of marriage. And after their divorce, Weston Jr. would eventually relocate in 1995 to his fourth home in Novi, Michigan. He lived there for nearly 30 years before his age, and poor health forced him to sell the house in June 2025.

In retirement, Weston Jr. usually stayed active by playing golf on the 9-hole golf course that his condominium sat on. And he often joined golf leagues within that neighborly golf community. He was also a frequent traveler to Europe. Visiting Paris, Amsterdam, Venice, Germany, Verona, and Barcelona. Weston Jr. also globetrotted to hot spots like Brazil and Martinique, and kept a timeshare in Orlando, Florida. And when he wasn't golfing or traveling outside of the United States, he would visit old college friends in New York and Washington, D.C., or when he needed a change of pace and retirement life got just a little boring for him. Weston Jr. would at various times pull himself out of retirement by rejoining his old employer, Health Alliance Plan ( HAP ), as a consultant during the health care industry's most critical recruitment time. Weston Jr. also would go on to volunteer for 5 years to the Lions Club International Charity. And was a Life Member of the National Association for the Advancement of Colored People. As well as serve as Vice President of the Cass Tech Alumni Triangle Society.

After 19 years of retirement, Weston Jr. was diagnosed with kidney failure. His endocrinologist gave him a five-year life expectancy prognosis so long as he continued his dialysis sessions. Incredibly, Weston Jr. outlived his doctor's earlier prognosis by approximately one year and six months. It has been amazing and literally shocking to witness just how strong-willed and resilient he showed himself to be. It seemed that he routinely bounced back and overcame his health setbacks, time and time again. And through all of it, he kept a cheerful attitude. Especially when dealing with doctors and hospital staff. In the end, Weston Jr. decided to take his fate and his destiny into his own hands. Although barely able to walk around for any long distances, he was very determined not to be permanently assigned to a wheelchair. And he also would still drive himself to his dialysis sessions, three days per week. As the disease continued to take a toll on his body. And as he grew weaker and weaker, he called for a family conference to talk about his life choices and his future going forward. At 88 years of age, Weston Jr. decided to terminate his dialysis sessions. He had concluded that he wasn't living life anymore. His family respectfully honored his wishes. Every man enters that threshold where death overtakes them. Weston Jr. stepped down on his own terms with dignity.

HE LIVED A FULL LIFE

Weston was preceded in death by his parents, Weston Diggs Sr., Edna Tillery, his stepmother Charlye Diggs, his brother John Diggs, and his sister Charlita Diggs.

Weston is survived by his son, Weston C. Diggs III of Rochester Hills, MI, his daughter Annette K. Diggs of Rochester Hills, MI, His son Anthony W. Diggs of Denver, Colorado, and his beloved Granddaughter Denise Diggs of Rochester Hills, MI.

In lieu of flowers, the family requests that donations be made in Weston's memory to the Lions Club charity and the Alzheimer's Association.
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