This Veteran’s Day, we pause to honor the life and service of John Cyril Robertson, a World War I veteran whose story with Chicago Scots begins not on a battlefield, but at the summer picnic held by Caledonia Senior Living & Memory Care.
John Cyril, a proud Scottish immigrant, was just 17 years old when he attended that community gathering—a place where Scottish families came together to celebrate heritage, connection, and tradition. That day, members of the 48th Highlanders of Canada, a distinguished Scottish infantry regiment, were present, recruiting young men to serve in the war. Inspired by duty, tradition, and courage, young John Cyril enlisted. Two other friends joined him, and he trained as a machine gunner.
The 48th Highlanders of Canada, with deep Scottish roots, held a strong presence across North America. Their connection to The Scottish Home and the broader Chicago Scots community created a meaningful bridge between heritage and service. For John Cyril Robertson, this connection was deeply personal—his family had immigrated from Scotland in 1912 and embraced Chicago as their new home.
A Life of Service and Sacrifice
After serving bravely overseas, John Cyril returned to Chicago. He altered his discharge papers making himself appear older and he joined the Chicago Police Department. Once again he found himself at a picnic at The Scottish Home—this time not to enlist, but to begin the next chapter of his life. It was there he met his future wife Loretta, through his sister, Louise. Though the family had believed Loretta to be of Irish and German descent, research through Ancestry.com later revealed she was entirely Irish. Their marriage was also interreligious—John Cyril was Methodist and Loretta was Catholic—a notable detail in that era.
The couple settled into life in the 1920s in what is now Elmwood Park, raising a son and later a daughter, Rita. Sadly, tragedy struck early. In 1933, at just 34 years old, John Cyril passed away from liver disease, the result of coping with the lingering pain of his war wounds. His son, only 7 at the time, would grow up during the harsh years of the Great Depression, a time marked by resilience and sacrifice.
Loretta, left to care for two young children, moved in with her mother’s family. Even their beloved family dog had to be given away during those difficult times. But despite the challenges, the legacy of service continued. John Cyril Robertson’s grandson, who shares the same name, went on to become a Sergeant with the Chicago Police Department, earning recognition—including a plaque from the Chicago White Sox.
A Great Granddaughter’s Tribute
Libby, a great grandchild of John Cyril Robertson, has worked to preserve her grandfather’s memory. Before her grandfather, John James Robertson, passed away from complications due to COVID-19 a few years ago, Libby helped him write down their family story—an act of love and remembrance.
This summer, Libby returned to the summer picnic at The Scottish Home, bringing her three children to experience the tradition that shaped generations of her family.
The Robertson family still carries their family tartan and rose, a proud symbol of their Scottish heritage and the sacrifices made across generations.
Four Generations, including Libby, her daughter Franchesca, her Father John Cyril Robertson and her Grandfather John James Robertson
Libby’s three children at the 2025 Caledonia Senior Living & Memory Care Summer Picnic
Remembering John Cyril Robertson
This Veteran’s Day, we remember John Cyril Robertson not just for his military service, but for the life he led, the family he raised, and the legacy of resilience and public service that followed. His story reminds us that behind every uniform is a rich tapestry of culture, sacrifice, and community —and sometimes, it all begins with a summer picnic.
Share Your Family’s Story
At Caledonia, we believe in the power of family and invite you to share your family’s connection to our community by emailing info@caledoniaseniorliving.org.