Robert Sterling Bailey

Robert “Bob” Bailey, of Estero, Florida (formerly of Carmel and Speedway, Indiana), passed away peacefully on March 26, 2026, at the age of 95, leaving behind a legacy of optimism, generosity, and a life enthusiastically lived.

Bob was the beloved husband of Jackie Ford Bailey, with whom he shared 64 wonderful years of marriage: years filled with laughter, partnership, and unwavering love. Together, they built a life centered on faith, family, friendship, and making the most of every single day.

He is survived by his three daughters: Kimberle Badinelli (Ralph), Barbara Martino (Tom), and Jennifer Miller (Lou), who carry forward his spirit of positivity and kindness. He was a proud and devoted grandfather to Carmen, Nick and Jake Badinelli, and Patrick and Madeline Miller (Cannon). His joy multiplied with the arrival of his cherished “littles,” his great-grandchildren: Ben and Amelia Miller; Ava and Olivia Badinelli; and Eve and Lucy Cannon.

Bob had a gift for seeing the world not just as a glass half full but, as he often showed those around him, about 98% full. He believed deeply in optimism, and more importantly, he lived it in a way that lifted everyone around him.

Bob and Jackie loved to travel and enjoyed many cruises together, hosting their entire family on a 50th anniversary cruise in 2004. They were generous hosts to family and friends for decades at the various timeshare properties they owned.

His faith was important to him from a young age, but he often remarked how the CHIRP and This Man is You programs at St. Elizabeth Seton gave him new perspective on what it was to live his faith. Once they moved to Florida, he and Jackie became active participants in the Hearts Afire Parish Program at Our Lady of Light, and Bob continued with many Bible studies.

A man of many passions, Bob was a lifelong fan of IndyCar racing, attending races for more than 60 years—proof that once he loved something, he stayed all in. He supported his Alma Mater for decades as a proud member of the John Purdue Club. He was also a longtime member of Toastmasters, where he shared his love of speaking, storytelling, and connecting with people, whether addressing a crowd or enjoying a one-on-one conversation. Bob was honored as the Knight of the Year in 2025 in Our Lady of the Rosary Assembly 2542 of the Knights of Columbus. He was a past national president of Phi Kappa Theta Fraternity and active in Optimists and Junior Achievement.

After gaining his BS and MS in Chemical Engineering at Purdue, Bob spent his entire career at Lilly Industrial Coatings in Indianapolis, where he went from roles as Technical Director to Sales and Marketing and finally General Manager of the Indianapolis plant.

At age 90, Bob decided he would continue to learn. He started with piano lessons, learned to play bocce and how to make a perfect grilled cheese (the secret is lots of Kerry Gold butter on the bread). He invested in a fat-tire adult tricycle and was known as the “Mayor of Belle Lago” riding around the neighborhood and learning everyone’s name and life story. His six year annual Fudge Caper initiated with daughter Kimberle, made him a popular neighbor.

Bob’s greatest joy was people. He loved his family fiercely, cherished his many friendships, and never met a stranger for long. In retirement, he dedicated over 20 years to mentoring aspiring entrepreneurs through SCORE, helping others bring their dreams to life with the same encouragement and belief he carried in his own heart. One SCORE member said of Bob “He was both the oldest member or our chapter, and the youngest.”

He also made sure his grandchildren understood the importance of giving. Each Christmas, he would take them to a toy store—not just to receive, but to choose gifts for children in need—quietly teaching lessons of compassion that will last for generations.

Bob lived life fully and with intention. He never wanted to miss an experience, whether it was a new adventure, a gathering of loved ones, or simply the opportunity to enjoy a good glass of wine or a fine bourbon. He found joy in the everyday and reminded others to do the same. He will be remembered for his warmth, his humor, his boundless curiosity, and his unwavering belief that life is meant to be savored.

In honoring Bob, his family invites all who knew him to raise a glass, share a story, and, most importantly, look at life the way he did—98% full.

Memorial Donations made be made to 40 Days for Life, Diocese of Venice, 1000 Pinebrook Road, Venice, FL 34285; or the Knights of Columbus, Council 10498, 19680 Cypress View Drive, Fort Myers, FL 33967.

A funeral Mass will be celebrated at Our Lady of Light Catholic Church in Estero on April 28th at 11:30 am followed by a lunch reception at Estero Country Club.

A Memorial Mass will be offered on June 12th at 10:30 am at St. Elizabeth Seton Parish in Carmel, Indiana followed by a luncheon reception at the church immediately after the Mass. Committal and interment will be at Oaklawn Memorial Gardens in Indianapolis.