Leon LeRoy: Reflections on a life well-lived

By Tracy Poyser

There’s something special about our intergenerational community that invites sharing. So, when our neighbor Leon LeRoy celebrated his 95th birthday in December, we asked him for a glimpse into his long, remarkable life. No, he’s not a celebrity, but a man of quiet dignity, elegance and grace who defied many obstacles with resilience, hard work, perseverance and faith. You’ll recognize him from this photo – always impeccably dressed, whether in casual or formal wear, with a smile for everyone.

“I love people, and all my jobs were connected with people,” he said.

Leon was born in 1923 in Vicksburg, Miss. His father was only 39 when he died in 1939, leaving his mother to raise their four children alone. In 1940, she moved the family to St. Louis. She worked hard all her life but never remarried. Before Leon finished high school in 1942, his mother had taught him to drive her truck. He left for Chicago immediately after graduation, where he knew just one friend, who helped him get settled. He was determined to work hard, but… “The only well-paying jobs for blacks at the time were with the police, the Postal Service and public transportation. I applied for the police but wasn’t tall enough,” he explained.

For 5-6 years, he worked three jobs a day.

“I became a hairdresser and was a salon owner at 76 E. Garfield, with five women working for me while I worked part-time,” he recalled. “Starting in 1948, I also drove a streetcar as a motorman for what was (previously) called the Chicago Surface Lines, and as a driver when it converted to buses only – today’s CTA. I worked there for 34 years and I was among the first blacks they took on. And, I worked at Beverly Bank as a bank teller.”

His workday meant getting up at 4 a.m., driving the streetcar or bus until around 8 a.m., then working in his salon until 2 p.m., and on to his teller job from 3-6 p.m. “I also took a course in interior design at the Harrington College of Design. And, I worked at Cage and Calahan funeral homes and the Unity Funeral Parlors as a limo driver. At Cage, I also assisted the funeral director for about 10 years – and was glad for the experience.”

He certainly lived the motto that hard work doesn’t kill you.

Leon met his beloved Wilhelmina as a neighbor. They began talking and realized they shared the same challenges. They were married from 1978 to 2003. With her position as a fifth-grade teacher and Leon’s hair salon and other endeavors, they were able to do well together. Travel was a big hobby for the couple – from their first monthlong bus tour of Europe in 1980 – and, when Wilhelmina was teaching, Leon traveled solo all over the world – Japan, Thailand, Hong Kong, Taiwan, the Philippines and Singapore. The couple once drove Route 66 all the way to California.

Leon enjoys living in Malibu East and has quite a few friends here. Before his last surgery, he worked out regularly in our Fitness Room and, weather permitting, walked 15 laps around our tennis court every day. “I served on the Board from 2009-12 and enjoyed the experience. Also, I’ve been helping the Social Committee, especially as barman for the holiday party for the last eight years.

“(Just prior to the 2018 holiday party) I had just returned from the Mayo Clinic in Rochester, Minn., where I had surgery on my right arm.” Four years earlier, as he was running to catch a #147 bus while downtown, he had fallen face-first and fractured bones in his right shoulder. After another fall two years later, lengthy hospital stays and many consultations with doctors who refused to do more surgery, he found an orthopedic surgeon at Mayo Clinic who agreed to do the surgery on his arm.

“I was willing to take the chance. My daughter flew with me to Rochester, and all went well. So here I am at 95 years old, going to PT and coming along fine. You see, I believe in faith, and with the help of the Almighty God, all things are possible.”

Leon’s sense for beauty and harmony is reflected in his apartment. He purchased his two-bedroom unit in 1978, initially renting it out before eventually moving here in 2003 after Wilhelmina had passed away following a long health battle. He then undertook extensive renovations of his condo. “I had both bathrooms remodeled with white marble,” he proudly related during my tour of his impeccable home, including an eye-catching custom closet for his impressive collection of dress suits and shoes. “At the ripe old age of 95, I hope to live a few more years to enjoy all that was done for my comfort.”

Leon’s condo is filled with photos of family and friends, including honors for his Wilhelmina. She had been a fifth-grade teacher and member of the Delta Sigma Theta sorority. The wall art reflects his travels – original framed prints from Hong Kong and China, and beautiful copper and glass artifacts.

Leon has been a longtime member of the Chicago Assembly, one of the oldest and most prestigious social clubs in Cook County. The all-male membership consists of 250-plus successful black Chicago businessmen from all walks of life. He has wonderful photos of their social events, especially the elegant Holiday Ball held each year at the Hyatt Regency Chicago, with the men dressed in black tuxedos and black bow ties, and the women in formal floor-length dresses.

Leon loves living, but he has also planned for his death, purchasing a crypt next to Wilhelmina and prepaying all other funeral expenses, so his children won’t have to worry. Leon has a son and two daughters from former marriages, both born in the late 1940s, with one daughter living in Santa Ana, Calif., and the other in the southwest suburb of Lynwood.

Leon’s just waiting for his arm to get better so he can write a book. With his grandson’s help, he’ll use his new laptop.

“I’m never too old to learn new tricks,” he chuckled.

He’s not quite computer-literate yet, but he does have a Facebook account, so do friend him!