James R. Pender

James Robert Pender
January 11, 1938 – September 4, 2026

Born in Philadelphia on January 11, 1938, Jim was raised in Webster Groves, Missouri, the small town he always considered home. It was there that he learned lessons he carried throughout his life: work hard, be a good teammate, be loyal to your friends and family, maintain a positive attitude, and always be grateful for what you have.

Those who knew Jim will recognize the words he continued to use even during his final days. When someone asked how he was doing, despite declining health, an ICU stay and, ultimately, hospice care, his answer remained the same: “Never Been Better.” That was Jim. He was grateful for the people caring for him, grateful for his family and deeply grateful for his friends.

Jim was the son of Marcus Watson Pender and Margaret Oswald Pender. He is survived by his beloved wife, Kathy Chilcote Pender, with whom he shared 65 years of marriage; his daughter, Katherine “Katie” Clark, and her husband, Jeremy; his son, Marc Matthew Pender; and his grandchildren, Matthew and Charlotte Pender, and Katherine and Tyler Clark. He is also survived by his sister, Susan Hollister, as well as nieces and great nieces.

Jim and Kathy were predeceased by their son, Michael James Pender, who died in 1991. Michael remained an important presence in their lives, and together Jim and Kathy found many ways to honor his memory by helping children and families throughout the Cleveland community. Jim also leaves behind two particularly devoted members of the Pender household, his beloved Cavalier King Charles Spaniels, Zoe and Lucy.

Jim was the former Chairman and CEO of Oswald Companies. The grandson of founder James B. Oswald and the last member of the family to lead the organization, Jim helped grow Oswald into one of the largest privately held insurance agencies in the country. Today, it remains one of the nation’s oldest and largest employee-owned insurance agencies.

Perhaps nothing better reflected Jim’s philosophy of leadership than his decision to transfer a portion of his ownership into a trust for the benefit of employees. He believed that success should be shared with the people who helped create it.

Jim was also active throughout the insurance profession. He served as president of the Cleveland Chapter of the Chartered Property and Casualty Underwriters and taught several courses. He was a founding member and chairman of Assure Global International and served as an officer of the Washington, D.C.-based Council of Insurance Agents & Brokers. Throughout his career, he was a mentor and trusted advisor to many.

His commitment to service extended well beyond his professional life.

Jim and Kathy’s long relationship with Playhouse Square has a particularly personal beginning. They first meet at age 16 on a blind date to see Gone with the Wind. Seven years later, they were married. In time, Jim became an active member of the Playhouse Square Board of Trustees and ultimately a Life Trustee. He served on its education committee, and he and Kathy supported programs for children in memory of Michael. Jim’s commitment to Playhouse Square was recognized with the Falco Award.

He also served on the leadership advisory board of Beech Brook and chaired the board of Camp Ho Mita Koda, serving children with diabetes. He was involved with the Cleveland Foundation, where a fund established in Michael’s memory helped support children and programs addressing special needs.

For many years, Jim served on the Board of Trustees of Gilmour Academy, a school that held a particularly meaningful place in the Pender family’s life. Both sons, Marc and Michael, and four grandchildren graduated from Gilmour. Despite health challenges during his years there, Michael embraced every part of campus life and formed a deep attachment to the school. He died the year after his graduation from complications following a transplant.

In the decades that followed, Jim and Kathy honored Michael’s memory through their continued involvement and significant philanthropy with Gilmour and remained devoted to the school as their grandchildren made their own way through the Academy. Jim took great pride in watching his grandchildren become part of a school that had held such an important place in the life of their family.

Jim and Kathy also supported programs at University Hospitals, including Connor Whole Health, and a special room was created at Rainbow Babies & Children’s Hospital in Michael’s memory to provide comfort and support to families of children receiving intensive care.

Jim loved Gates Mills, where he and Kathy made their home for nearly 50 years. He served on several village committees and valued both the beauty of the community and, even more, the friendships they made there.

Sports were another constant in Jim’s life. He loved baseball and football and could recite the starting lineups of great Cleveland Indians teams from years ago. He began playing football as a teenager in Webster Groves and believed throughout his life that many of the lessons that helped him succeed had first been learned on an athletic field.

After moving to Cleveland, Jim met Jack Herrick, and the two bonded over squash. They played together for many years and became close friends, a friendship that eventually led to Jim’s involvement with the Greater Cleveland Sports Hall of Fame. He served on its board for more than 20 years. For Jim, sports were especially meaningful when he had someone to cheer for. When his children and grandchildren became involved in sports, he was their biggest fan and attended as many games and events as he possibly could. As part of his legacy, his support of youth sports will continue through the Greater Cleveland Sports Hall of Fame.

Jim was also remarkably disciplined about his own fitness. He maintained an exercise routine until very late in his life. Even as his physical health became more challenging, he remained determined to keep moving and maintained the positive outlook that had defined him throughout his life.

Jim never stopped wanting to learn. His inquisitive mind stayed with him until the final weeks of his life. He was constantly searching for something new to read, someone interesting to talk with, or an idea worth debating. That curiosity was one of the reasons he loved Chautauqua, where he eagerly attended and evaluated lectures and presentations.

By any account, Jim’s life would be incomplete without his sense of humor. Life with Jim was fun, and no one could ever be entirely certain what he might dream up next. His Yale friends and roommates knew his antics well. He might appear at the airport dressed as a Buzzy Bee, arrive on Valentine’s Day as Cupid, or find some other excuse to put on a costume. At Christmas, Jim loved being Santa Claus. He became the center of the celebration and a source of delight for generations of family and friends. Kathy has wisely preserved the costumes in the family’s “costume room,” ready for future generations to continue the tradition.

And then there were the Stemples — Marge and Jack, their children and their dog, Emps. For years, Christmas letters describing the adventures of this completely fictitious and rather awkward family arrived in mailboxes around the country. At first, recipients had no idea who these strange people were. Eventually, word got around: the Stemples existed only in the wonderfully mischievous imagination of Jim Pender.

Behind the humor was a man who cared deeply about people.

Jim created a remarkable picture diary of the people in his life — family, high school friends, college friends, weddings, birthdays, babies and countless gatherings. Years later, a photograph might unexpectedly arrive from Jim, reminding someone of a moment they had shared long ago. It was his way of remembering people and letting them know that they mattered to him. He treasured the times his family could be together and was genuinely interested in the lives of younger generations. He wanted to know what they were doing, what they were thinking and what they could teach him.

His friendships also endured across decades. He maintained close relationships with friends from University School, whose Class of 1955 adopted Jim as one of their own, and he remained in regular contact with his Yale classmates throughout his life.

Underlying Jim’s family life, friendships, service and optimism was a deep and sustaining faith. Jim and Kathy shared that faith and tried to make it the foundation for how they lived their lives. Jim was a longtime member of St. Christopher’s Church in Gates Mills, where he served as a Eucharistic minister and member of the vestry. Each morning, Jim spent time reading prayers he had collected over the years. It was a ritual he rarely missed. During his final days in hospice, when he could no longer maintain that morning ritual himself, his family read many of those same prayers to him. It was a fitting way to honor a man whose life had been centered on faith, family, friendship, service and gratitude.

Jim leaves behind an extraordinary number of family and friends who loved him, laughed with him, learned from him and were better for having known him. His accomplishments were many, but those closest to him will remember something simpler: his loyalty, his curiosity, his humor, his love of family, his faith, and that unmistakable determination to find something good in every day.

It was an outlook Jim carried with him throughout his life, and one he summed up in three words better than anyone else could: “Never Been Better.”

In lieu of flowers, the family requests that donations be made in Jim’s memory to Gilmour Academy, 2045 SOM Center Road Gates Mills, OH 44040, or to Reserve Care, formerly Hospice of the Western Reserve, at PO Box 72700, Cleveland, OH 44192, or any of the other non-profits that were special to Jim.

A Funeral Service will be held on Saturday, September 19 at 1:30 p.m. at Our Lady Chapel on the campus of Gilmour Academy, 2045 SOM Center Road, Gates Mills, Ohio.

The Funeral Service will also be livestreamed and available at www.Gilmour.org/live.