Lawrence “Larry” M. Ryan, a Chicago native who built a life spanning continents and careers, and ultimately found a second home in Naples, Florida, died on March 15, 2026, at the age of 94. His life, marked by early displacement and entrepreneurial spirit, was a testament to resilience and the enduring power of family. Ryan’s story reflects a generation shaped by global shifts and the pursuit of the American dream, a journey that began on a wheat ranch in Mexico and culminated in a vibrant life surrounded by a large and loving family.
Born June 4, 1931, in Chicago, Illinois, to William and Mary Bolger Ryan, Larry’s early childhood took an unexpected turn when his family relocated to Cajeme, Mexico, where his father pioneered wheat and rice farming. This period, lasting until he was eight years old, shaped his early understanding of the world, but was abruptly altered by political upheaval. The Mexican government’s nationalization of foreign-owned property forced the family to return to the United States, settling in Oak Park, Illinois. This experience, although disruptive, instilled in Ryan a lifelong adaptability and a deep appreciation for stability.
Ryan excelled academically, graduating from Loyola University in Chicago. It was there he met Frances “Cupcake” Cutler, whom he would marry and with whom he would build a family. He entered the wholesale women’s apparel business, establishing offices and showrooms at Chicago’s iconic Merchandise Mart and later in the Chicago Apparel Center. For decades, he navigated the competitive world of fashion, demonstrating a keen business acumen and a commitment to quality. The Merchandise Mart, a landmark of Chicago commerce, is still a major hub for apparel businesses today. Learn more about the Merchandise Mart.
A Life Centered on Family and Recreation
Beyond his professional life, Larry Ryan was deeply devoted to his family and enjoyed an active lifestyle. He and Fran were avid tennis players, frequenting the Oak Park Tennis Club and Oak Brook Tennis Club for many years. Their love of the sport led them to purchase a condominium at the Naples Bath and Tennis Club in the 1980s, a move that foreshadowed his eventual relocation to Southwest Florida. But, Fran’s battle with a brain tumor tragically cut their time there short. Following her death, Ryan continued to visit Naples, drawn to its warm climate and relaxed atmosphere, eventually making Pelican Bay his permanent residence.
In 1999, Ryan found love again, marrying Nancy “E.T.C.” Murphy Carroll, a long-time neighbor from River Forest. This union expanded his family to include Nancy’s four children – John “Jay,” Tim, Chrissy “I.G.I.,” and Murphy Carroll – and a growing number of grandchildren. He embraced his role as a stepfather and grandfather, cherishing the opportunity to witness their lives unfold. The affectionate nicknames bestowed upon the grandchildren – Johnnie “I Doubt It,” Matthew, Colin “3-point,” “Touchdown Charlie,” “Pinky,” “Majesty,” “Hat Trick,” and “Spike” Carroll – speak to a playful and loving spirit.
From Mexico to Florida: A Legacy of Resilience
The early years spent on his father’s ranch in Cajeme, Mexico, now Ciudad Obregon, Sonora, Mexico, were formative for Ryan. His father’s pioneering efforts in farming wheat and rice were ultimately thwarted by the Mexican government’s expropriation of foreign-owned land. This event, while a significant loss for the family, instilled in Ryan a sense of perspective and a determination to build a secure future. The history of land reform in Mexico during the 20th century was complex and often contentious, impacting many foreign landowners. Learn more about the Mexican Revolution and land reform.
Ryan’s five sons – Lawrence “Larry,” John “Jake,” Timothy “Tinx”, Peter “Peps,” and Daniel “Danny” Ryan – brought him immense joy, and his children and grandchildren, Peter “Pete,” Kelly “Kell Bell,” Jack, Kate, Brianna “Bree,” Connor, Doug, Mia, Mara, Cade and Holly, along with great-grandchildren Charlotte “Charlie Pebbles,” Paige “Paigey,” Pearson “Bopples,” Joan “Joanie” and Simone “Ya-Ya,” were the center of his world. He was affectionately known as “Grampy” or “Pops,” titles he cherished. The expansive family network reflects a life well-lived and a legacy of love that will endure for generations.
Remembering Larry Ryan
In lieu of flowers, Larry Ryan requested that friends and family send a note to his wife, Nancy, so she can create a remembrance album. This simple request speaks volumes about his thoughtfulness and his desire to leave behind a tangible reminder of the connections he forged throughout his life. A Memorial Visitation will be held on Wednesday, April 29th at St. Vincent Ferrer Church in River Forest, Illinois, from 9:15 a.m. Until the time of mass at 10:00 a.m. Arrangements are being handled by Peterson-Bassi Chapels. Peterson-Bassi Chapels website.
Larry Ryan’s passing marks the end of an era for his family and friends. His life story, from the challenges of his early years to the joys of a large and loving family, serves as an inspiration. The family plans to continue gathering and sharing memories of Larry in the years to come, ensuring his spirit lives on. Further details regarding a potential celebration of life event in Naples will be shared by the family at a later date.
Please share your memories of Larry in the comments below.
