Oscar "Dick" Davis Bailey, Jr.

Oscar D. (Dick) Bailey, 92, of Greenwood, DE, passed away at his home on July 21, 2025. He was born on April 29, 1933 in Slaughter Neck, DE, son of the late Oscar and Mildred (Savage) Bailey. He was a veteran of the United States Air Force serving during the Korean War. This was followed with continued service to our Country in the Merchant Marine and Coast Guard Reserve.

Oscar was a proud veteran who leaves behind a legacy of service, dedication, and strength. A steadfast man devoted to his community, Oscar was as a district commissioner for the Boy Scouts of America, where he inspired generations of young men through mentorship and leadership. During that time, he earned a distinguished service award, the Silver Beaver, and was a member of the Order of the Arrow. He was an active member of the Rotary Club and the local HAM Radio Club. Oscar found joy and peace in the outdoors, often spending his time hiking, fishing, and hunting. When not exploring nature, he could be found with a book in hand, always eager to learn. His unwavering values and deep love for his country and his family will be fondly remembered by all who knew him.

In addition to his parents, he is preceded in death by his wife Janet Worthington Bailey. 

Dick is survived by former wife Patricia Jopp Bailey. He often stated that his greatest gift from God was his three beloved daughters- Susan Esham and husband Timmy, Carol Reed and husband Paul, and Michele Peiffer and husband Shane. In addition he was loved, admired and will be deeply missed by the grandchildren; Adam Reed and his wife Selena, Kayla Peterman and her husband Joel, Kelsey Snyder and her husband Andrew, Mackenzie Reed, and Rebekah Peiffer. He will be deeply missed by his great grandson Isaac Peterman. He is also survived by his sister Phyllis Smith; as well as various nieces, nephews, and extended family members.

A memorial service to celebrate and honor Oscar Bailey Jr.'s life will be held on Monday, July 28, 2025, in the chapel of Berry- Short Funeral Home in Milford, DE. A time of visitation will be held from 10:00 am to 11:00am with a funeral service and military honors immediately following at 11:00 am.