Robert J. "Bob" Bailor Sr.

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Robert J. Bailor Sr. (Bob), a beloved husband, father, grandfather, and great grandfather passed away peacefully surrounded by his loved ones on February 25, 2024, at the age of 79. He leaves behind a legacy of love, humor, adventure, and unwavering dedication to his family.
Born on September 2, 1944, in Baltimore City to Francis Bailor, Sr and Annabelle [Schultz] Bailor, Bob was the 2nd of 5 children, Frank, Tom, Ed and Marianne. Bob's passion for the sea was evident from a young age as he spent countless hours playing in or on the waters of the Chesapeake Bay, finding solace and joy in the embrace of the bay's gentle breeze. His love for the bay included sailing, fishing, and crabbing which deepened over the years due to his adventurous spirit. This spirit led him to proudly serve his country in the United States Navy, where he bravely defended the freedom's that we hold dear. He carried the values of duty, honor, and sacrifice throughout his life proudly serving his country during Desert Storm and Desert Shield eventually retiring from the Delaware Air National Guard after 35 years. Bob had a fulfilling and by the stories he told, fun, career at Dupont's retiring to assist and care for his parents in their final years who preceded in death.
A true son of the Chesapeake Bay, Bob had a deep connection to the water. Sailing the bay's green expanse, fishing its bounty, or crabbing along its shores which brought him immense happiness and serenity. His love for crabbing and fishing were not merely hobbies but a way of life placing his lines and setting his traps with skill and determination. One of his favorite things to do after a long day of sailing the bay was to raft up with as many friends and family who could attend in a random cove in the Chesapeake for a wonderful weekend. His laughter and camaraderie echoed across the waves, creating cherished memories that will endure for generations.
Above all, Bob cherished time with his family. He was a devoted husband to his wife, Mary, with whom he married on Dec 10, 1966, celebrating 57 years this past December. He was a loving and gentle father to his four children, Robert Jr. Bailor and his wife, Michelle (Onorato) Bailor; Elizabeth (Bailor)Wyatt and her husband Rich Wyatt; Douglass Bailor and his partner Diana Soto; and Andrew Bailor and his wife Ania (Jaworska) Bailor. Bob was a pillar of strength and support for his family, always there to offer a listening ear, a comforting embrace, or words of wisdom. His family was the anchor of his life, and he found immeasurable happiness in their company, whether gathered around the dinner table, vacationing, or exploring the many coves and endless coastlines of the bay together. His many trips in West Virginia visiting his wife's family included hunting, exploring, and developing lifelong friendships with extended family.
Bob loved to share stories, play cards and other games, going to the casino, or simply telling silly jokes together. Bob cherished every moment spent with his family, leaving an indelible imprint on their hearts. Bob loved deeply each grandchild, and great grandchild and they were the center of his world where he found immense joy in watching them grow and thrive.
His grandchildren and their spouses include: Joanna Bailor and her partner Phillip Jester; Annabell (Bailor) Healy, her husband Brett Healy; Christina (Bailor) Steele, her husband Chayce Steele; Robert Bailor III; Samson Bailor; David Bailor; Amanda (Andrews) Pedicone and her Husband Kyle Pedicone; Rachael (Andrews) Shores and her husband John Shores (proceeded in death on 11/22/2022); Matthew Andrews and his wife Angel (Ward) Andrews; Dustin Wyatt; Kathleen (Wyatt) Massey;, Brian Wyatt; Ian Wyatt; Kade Bailor; Koen Bailor; Aleksandra "Sasha" Bailor; Lucas Bailor. His Great Grandchildren included: Aiden Shores; Leland Shores; Ophelia Shores; Kylee Pedicone; Garrett Pedicone; Sierra Pedicone; Catalaya Andrews; Matthew Andrews Jr.; Illana Andrews; Kingston Jester and Emma Jester. Bob was loved by an incredibly large extended family that had over 30 nieces and nephews, many 1st and 2nd cousins, and a large loving in-law family each with special memories, stories, and tales of their own.
His unconditional love and unwavering presence brought solace and comfort to those around him, and his absence leaves a void that can never be filled. Bob's kindness, generosity, and zest for life touched the hearts of all who knew him that instantly made them feel like family.
Though he has set sail on his final voyage, his spirit will forever remain in the wind, the waves, and the hearts of those who loved him. May he rest in eternal peace, sailing on calm waters, and forever remembered for his love, loyalty, and enduring legacy. Fair winds and following seas Dad. May your sails always be full, and your spirit forever free. May you finally catch "Big Blue".
You will be missed but never forgotten.
A viewing will take place on Wednesday, March 13th from 1-2 PM, the funeral service will begin at 2:00 PM at Daniels & Hutchison Funeral Home, 212 N. Broad St., Middletown, DE 19709.
A committal service with military honors will be held on Wednesday, April 3rd at 11:00 am in the Delaware Veterans Memorial Cemetery Chapel, 2465 Chesapeake City Rd., Bear, DE 19701. Visit Daniels-Hutchison.com to read the complete obituary.