Samuel Matthew Bailey Jr., affectionately known as “Bo,” of Coltons Point, Maryland, passed away peacefully at his home on May 23, 2026, at the age of 94. Born on July 19, 1931, in Milestown, Maryland, he was the son of the late Capt. Sam Bailey and Mignonette Bailey. A graduate of St. Mary’s Academy, Class of 1948, Bo remained a lifelong resident of the 7th District of St. Mary’s County, where he built a life defined by generosity and deep devotion to his family and community.
After working in the family trucking business and serving in the United States Army during the Korean War, with service at Fort Eustis, Virginia, Bo embarked on an entrepreneurial journey that would span more than five decades. He owned and operated several successful local businesses, including Capt. Sam’s Seafood, Capt. Sam’s Liquors and DJ’s One Stop Shop, before retiring in 2006. Bo was also known for his warm spirit and open door. He loved to travel, treasured time with family and lifelong friends, and found joy in simple acts of kindness. The welcome mat was always out.
A man deeply committed to St. Mary’s County Bo gave generously of his time and talents without ever seeking recognition. He continued his father’s legacy of community involvement through countless acts of kindness and longstanding support for local causes in addition to leaving his own mark on the community. In 1992 Bo garnered support from the community to start ACTS, lending durable medical equipment to the residents of the county. He was a proud charter member and founding member of the 7th District Optimist, St. Clement’s Hundred and St. Clement’s Island Museum. Bo was a faithful member of Holy Angels Catholic Church and served in many roles throughout his life, including director, board member, past president, and supporter of organizations that strengthened the community he loved. He proudly served on the boards of SMECO and the First National Bank of St. Mary’s for over 30 years respectfully. Bo’s life was marked by loyalty, humility, and an unwavering willingness to help others. His memory will live on in the many lives he touched and, in the family and community he loved so dearly.
Bo shared a special bond with his siblings and was fiercely proud of his family, encouraging them to always demonstrate respect, generosity, and compassion. He was a true optimist and always searched for the positive in every situation. Bo is survived by his beloved wife, Rose Beitzell Bailey; his children, Faye (Joe) Gowran of Groveland, Florida, Sam (Jen) Bailey III of Coltons Point, Maryland, Beverly (Larry) Wood of Mechanicsville, Maryland, Steve (Kay) Bailey Sr. of Bushwood, Maryland, John (Tracey) Cosimano of Alexandria, Virginia, and Tony (Lindsey) Cosimano of Kilmarnock, Virginia; his sister, Kitty Swann; his brother, Bernard Bailey; 11 grandchildren; 19 great-grandchildren; and many extended family members and dear friends. In addition to his parents, he was preceded in death by his wives, Joan (Coale) Bailey and Louanne (Cosimano) Bailey; son, Mark Bailey Sr.; his sisters, Eleanor Tippett and Lucille Doepkins; and his brother, Eddie Bailey.
The family will receive friends on Tuesday, June 2, 2026, from 4:00 PM to 8:00 PM. with American Legion prayers recited at 7:00 PM followed by Optimist prayers at 7:15 PM and Vigil Prayers at 7:30 PM in Holy Angels Catholic Church, Avenue, MD. A Mass of Christian Burial will be celebrated on Wednesday, June 3, 2026, at 10:00 AM. with Father James Myers officiating. Interment to follow in Sacred Heart Catholic Church Cemetery, Bushwood, MD. Serving as pallbearers will be Steven Bailey, Jr., Will Fitzgerald, Mark Andrew Bailey, John G. Fitzgerald, Larry Wood, and Mark Muir.
Contributions may be made to A.C.T.S. (A Community That Shares), P.O. Box 54, Bushwood, MD 20618.
Condolences may be made to the family at www.mgfh.com.
Arrangements provided by the Mattingley-Gardiner Funeral Home and Cremation Services, P.A., Leonardtown, MD.