Robert "Bob" Edward O'Leary, 74, passed away peacefully on July 26, 2026, surrounded by the love of his family.

Born on March 16, 1952, in Louisville, Kentucky, Bob was the son of the late Robert O'Leary and June Ann Ramsier Cherwak. From an early age, he possessed a strong work ethic, a kind heart, and a quiet determination that would define the way he lived his life.

Bob proudly served his country in the United States Navy as a helicopter mechanic. His service reflected the values he carried throughout his life—dedication, integrity, and a willingness to serve others. After his military service, he built a career in landscaping, where his gift for nurturing life became evident to everyone who knew him. Family and friends often joked that he could make anything grow, no matter how impossible it seemed. Whether tending a garden, repairing something broken, or building something with his own hands, Bob had an incredible talent for creating beauty and solving problems. There truly wasn't much he couldn't fix.

While Bob was proud of his work, nothing brought him greater happiness than his family. He shared a loving and devoted marriage with his wife, Teresa "Terri" (Armstrong) O'Leary, who was his partner and best friend. Together they built a life centered on love, laughter, and unwavering support for one another.

Bob's greatest pride and deepest joy were his children and grandchildren. He treasured every moment spent with them—whether telling stories, offering advice, teaching practical skills, or simply enjoying the little moments that became lifelong memories. His patience, wisdom, and unconditional love shaped the lives of those fortunate enough to call him Dad and Pop Pop. The lessons he taught, both spoken and by example, will continue to guide his family for generations to come.

Bob will be remembered for his gentle spirit, steadfast character, generous heart, and willingness to help anyone in need. He believed that hard work, kindness, and love for family were life's greatest accomplishments. Though his hands built countless things throughout his life, his greatest legacy is the family he loved so completely and the countless lives he touched with his quiet strength and compassion.

He is preceded in death by his parents, Robert O'Leary and June Cherwak (Ludy); his in-laws, Ed and Mary Shain; and his brother-in-law, David "Boney" Armstrong.

Bob leaves behind his beloved wife, Teresa "Terri" O'Leary; his sons, Craig O'Leary (Merrissa) and Bradlee O'Leary (Tiffany); and his treasured grandchildren, Roen Lathery, Emma "Hazel," Thomas "George," Maddox "Maddie," Aubrie, and Emerson, each of whom held a special place in his heart. He is also survived by his sisters, Lynda Wise (Andy) and Kathy Wareham (Eric); his brother-in-law, James "Jimmy" Armstrong (Brenda); as well as many nieces, nephews, great-nieces, great-nephews, extended family members, and dear friends who will forever remember the love, kindness, and wisdom he shared so freely.

Though Bob's presence will be deeply missed, his love lives on in every flower that blooms, every project completed with care, every lesson passed down, and every heart forever changed by knowing him. His memory will remain a source of comfort, strength, and inspiration to all who loved him.

Visitation for Bob will be from 11:00 AM to 7:00 PM on Saturday August 1, 2026 at Garr Funeral Home (7806 Highway 311 Sellersburg, Indiana 47172) with funeral services to follow at 7:00 PM also at Garr Funeral Home.