A Match Legacy Story: Simon & Jan (Yellowstone County)

Simon reached out through the Big Brothers Big Sisters contact page hoping to share the story of his match from Yellowstone County. He had been trying to reconnect with Big Brothers Big Sisters of Yellowstone County directly—only to learn that the agency closed in December of 2024. The news left him heartbroken. He wasn’t just looking for an organization; he was trying to honor a relationship that shaped his life. When our office called Simon, what was meant to be a short check-in became a nearly two-hour conversation. Coincidentally, the day we spoke marked the 30-year anniversary of his match with his Big Sister, Jan.

Simon was six years old when he and Jan were matched. Jan was decades older—four or five decades his senior—a highly educated woman who had worked as a nurse before becoming the head of a university nursing program. Jan had spent decades deeply committed to health and education on the Crow Reservation—not by returning to hospital work herself, but by actively recruiting nursing students from the Crow Reservation, supporting their education, and encouraging them to return home to serve their own community as nurses. She was also highly involved in health and wellness education on the Reservation more broadly. During COVID-19, when Simon’s work in the film industry shifted into COVID compliance, protocols, and safety guidelines, he noticed something striking while reviewing vaccination data nationwide: vaccination rates on the Crow Reservation were remarkably high, far surpassing those on many reservations across the country. Simon firmly believes this was not a coincidence. He attributes those life-saving outcomes to Jan’s decades of work building trust, knowledge, and access to health education—work that continued to protect the community long after her formal career ended.

As a child being raised by a single father, Simon lacked access to many cultural experiences—and to a consistent female role model. Jan changed that. She introduced him to theater, ballet, the symphony, and live music. Simon credits those early exposures as instrumental in shaping his creative life and eventual career in film. In addition to opening doors to cultural experiences and mentorship, Jan also made a tangible investment in Simon’s future by starting a college fund for him. That financial support made it possible for Simon to pursue higher education—an opportunity that may not otherwise have been within reach. He spoke about this not as charity, but as belief: Jan didn’t just encourage his potential; she backed it in a way that fundamentally altered the trajectory of his life.

Although Simon and his family moved away from Billings before he reached high school, the relationship did not end. They stayed in close touch, seeing each other at least once a year—often two or three times. They traveled together extensively, including overseas trips to Scotland, Wales, and Ireland. Before one international trip, Simon’s dad wrote and notarized a letter granting Jan permission to travel internationally with his son. Simon laughed as he recalled that not once during that trip did anyone question their relationship or ask for documentation.

Years later, during a spontaneous road trip to British Columbia, they weren’t so lucky. Stopped at the border, Jan—never one to be intimidated—got a little “spicy” when questioned about traveling with a teenage boy who wasn’t her son and had no paperwork. They were pulled aside and questioned separately. After extensive interrogation of a 15-year-old Simon, border officials eventually concluded there was no ill intent and allowed them to cross.

Jan and Simon called each other on every birthday and every match anniversary. She met his wife (whom he later divorced) and every significant partner he ever had. Last summer, Simon visited Jan in Billings to introduce his current partner and her twin daughters, whom he is helping raise. After a long evening visit, they stepped onto the porch to say goodbye—only to find themselves caught in a classic Billings thunderstorm. So they sat together, watching the lightning roll across the sky, just as they had so many times before. Simon described it as one of his favorite moments with her. He returned to Seattle the next day, already making plans to visit again. Less than a week later, Simon received the call that Jan had passed away. Jan had been diagnosed eight years earlier with a rare form of blood cancer. Simon researched the disease extensively and learned that individuals diagnosed at age 60 had less than a 20% chance of surviving two years. Jan was diagnosed in her late 70s—and lived eight more years. Simon said simply, “She was too stubborn to die.”

After her passing, several of Jan’s closest friends reached out to Simon. They told him they were certain Jan had been waiting to see him one last time before letting go. As Simon shared this story, he cried with someone he had never met before. He cried not only for Jan, but because the day he finally reached Big Brothers Big Sisters to tell their story was the first match anniversary in 30 years that he and Jan had not called each other to celebrate.

Toward the end of the call, Simon reflected on the women who shaped his life—Jan and her circle of strong, intelligent, powerful friends who didn’t tolerate nonsense and weren’t afraid to tell you when you needed to do better. He said that every time he introduced a significant partner to Jan, there was a moment of clarity.

“She’s why I turned out to be a good man.”