Robert Wayne Gillespie

Robert Wayne Gillespie, beloved husband, father, grandfather, and a towering figure in American banking, passed away peacefully on April 21, 2025, at the age of 81. He is survived by his cherished wife of 58 years, Ann, daughter Laura Gillespie and her husband Michael Martinez, daughter Gwen Gillespie Herman and her husband Josh, and six grandchildren who were the light of his later years: Spencer, Ella, and Jack Martinez; and Mira, Zoe, and Max Herman.

Bob’s life was defined by devotion—to his family, to his lifelong friends, to his work, and to the values of integrity, leadership, and generosity. He was born in Cleveland, Ohio, on March 26, 1944, and carried the lessons of a close-knit upbringing, shaped by hardworking parents and a principled grandfather, into a life of remarkable accomplishment and fulfillment.

His greatest fortune, Bob often said, came not from his career, but from meeting Ann at Ohio Wesleyan University. She was a gifted singer and a recent transfer from Eastman School of Music; he was a curious, charming young man with growing ambitions. Their love story began with a college variety show, when she caught his eye by dedicating a beautiful song to her father, and flourished into a marriage built on deep affection, mutual respect, and unwavering support. Together they faced the highs and lows of life with grace, laughter, and abiding faith in one another.

After earning his MBA from Case Western Reserve, Bob began his banking career at Society National Bank in 1968. Over the next four decades, he helped transform the small Cleveland institution into one of the most respected financial powerhouses in the country by spearheading transformative acquisitions, including Central National Bank, AmeriTrust, and ultimately KeyBank, a historic “merger of equals”—a bold, controversial, and ultimately visionary union that expanded the bank’s reach to markets across the nation. One of the highlights of his career was overseeing the construction of Cleveland’s iconic Key Tower. During this period, he also brought opportunities for the leadership of a Cleveland-headquartered bank to have a seat at the table in Washington, D.C. during significant periods of regulatory review and reform, serving on the boards of the American Bankers Association, President of the Federal Advisory Council of the Federal Reserve System, and as Chairman of the Financial Services Roundtable.

Bob’s tenure at Key was not just about building a bank; it was about building a better community. As a native Clevelander who grew up rooting for the hometown teams and visiting Nela Park for Christmas lights, Bob embraced the opportunity to give back to the city he loved. Both through KeyCorp and individually, he led major efforts in education, the arts, and social services. He served as co-chair of the Cleveland Bicentennial Commission and on the boards of numerous Cleveland institutions, including the following: United Way of Greater Cleveland; The Cleveland Museum of Art; The Cleveland Orchestra; Ohio Wesleyan University; Case Western Reserve University; City Year Cleveland; University Hospitals; and Breakthrough Schools.

At the heart of everything he did, however, were his family and dearest friends. Bob balanced a demanding career and active civic engagement with unwavering presence at choir concerts, field hockey games, and nightly dinners around the table. He was a doting father to Laura and Gwen, a loving father-in-law to Mike and Josh, and a deeply involved grandfather—ever proud of the remarkable young people they are becoming. Their homes throughout the years and their beloved Fairbow Farm were sanctuaries not only for their children and grandchildren, but for countless extended family and friends. After retiring in 2001, Bob turned his full attention to the joys of family, Sanibel Island sunsets, farm life, and philanthropy. He remained a mentor to many, a trusted advisor, and a steward of Cleveland’s civic soul. But more than anything, he cherished the simplicity of time with Ann, his family, and his beloved friends—gathered around a table, walking the land, or simply reflecting on a life well lived.

Bob’s legacy is enduring. It lives on in the institutions he built, the city he helped shape, and the family he adored beyond measure. His was a life of consequence, purpose, and deep personal joy. He will be missed beyond words—and remembered always with love.

A Celebration of Life will be held on Tuesday, May 13, 2025, at 3:00 p.m. at the Church of the Saviour (2537 Lee Road, Cleveland Heights, Ohio 44118), followed by a reception at the Chagrin Valley Hunt Club (7620 Old Mill Road, Gates Mills, Ohio 44040).

In lieu of flowers, the family asks that you consider a donation in his name to United Way of Greater Cleveland and Ohio Wesleyan University.