Jacqueline “Jackie” Winter Brown (or Grandma) is Kirby’s maternal grandmother. She launched Jackie & Daughter Flower Shop out of the side of her home in Topton, PA before expanding the business to Kutztown with her second-born daughter Shawn Brown.
Kirby considers Jackie instrumental in his creative development, having encouraged him from a young age to explore everything from art lessons to flower arrangements. His first album, Wasted Potential, was recorded using an old keyboard she gave to him. She died of natural causes in January 2024.
Background
Born in New Cumberland, York County, Pennsylvania, Jackie was the daughter of Earl and Catherine (Hopkins) Winter. She had two sisters, Maureen and Dorie, who frequently attended the family’s weekly Tuesday Night Dinners.
Her childhood was marked by frequent moves. Leroy “Jock” Brown often joked, “When rent came due, the family would move.” Eventually, she settled in Kutztown, where she first met Leroy. Jackie was working at a local spot and hid in a closet when Leroy first came in. Initially uninterested, she soon warmed up to him, and the two married on June 25, 1949.
Together, they had three daughters — Tonia, Shawn, and Shannon (Kirby’s mother). Jackie later founded Jackie & Daughter Flower Shop out of the side of their home in Topton. The shop eventually expanded into Kutztown when she and her daughter Shawn opened another location.
The flower shop became both a family enterprise and a formative environment for Kirby, who worked there after school — sweeping floors, prepping flowers, and accompanying Leroy on deliveries. Before GPS, Leroy mapped each route by hand, while Jackie maintained the creative pulse of the operation.
Influence on Kirby
Jackie played an essential role in Kirby’s upbringing and emotional development. He and his brother Beckham spent countless mornings before school eating breakfast with their grandparents, and during summer breaks, they played in the living room while Jackie worked in the adjoining flower shop.
She encouraged Kirby’s creativity from an early age, enrolling him in art lessons with local artist Joanne Lapic, where he explored oil pastels and portrait drawing. She also modeled what Kirby later called a “secular Lutheranism” — a quiet morality rooted in kindness and autonomy rather than dogma. Jackie often told him to “always be yourself,” never forcing religious belief or conformity.
While Kirby was in college, Jackie invited him to speak to her Bible Study group (affectionately called B.S. Group) about his atheism. He explained the historical and social roots of disbelief, noting that churches once served as central gathering places for community — a role now largely replaced by secular institutions. However, one BS Group member said later in the meeting that she saw God more as energy than an old man talking in the sky.
The exchange made Kirby reconsider the idea of religion altogether. Up until that point, he had dismissed faith as irrational precisely because it seemed predicated on a literal person in the sky. The discussion didn’t convert him, but it opened his mind and would later connect to his interest in Spinoza.
A few years later, Kirby recorded Wasted Potential using Jackie’s old keyboard, which had gathered dust for decades in the house. During his A Modern Man era, Kirby also came to understand Jackie’s long-term struggle with depression and her use of antidepressants.
After Jackie’s stroke, Kirby often joined his grandfather on Sunday visits to the nursing home. He was known for his ability to help her communicate, intuiting the words she couldn’t recall as she relearned speech. By her final Christmas in 2023, she was no longer herself, though her presence still anchored the family gatherings.
She passed away peacefully in January 2024, roughly two weeks before Kirby was set to leave for Los Angeles. Like his grandfather’s death, the moment brought a sense of calm more than devastation. “She’d already told me she was ready,” Kirby later reflected.