John Gregory Bailey, Sr.


image of John Gregory Bailey, Sr

John Gregory Bailey, Sr

John Gregory Bailey, Sr. was born in Seattle, WA, on May 20, 1934, and died in Redmond, WA, on April 10, 2023. He was preceded in death by his parents Homer and Helen Pfaff Bailey and his brother Joseph Bailey.  He is survived by his wife of 61 years, Donna Maxwell Bailey, children John (Nancy) Bailey Jr of Bellingham, WA, and Roberta Bailey (Markus) Roberts, of Forest Grove, OR; five grandchildren (Jack and Cory Bailey and Maxwell, Doña, and Walter Roberts) and his sister Ruthe Bailey Norton of Seattle.

Born in Seattle’s Ravenna district, John graduated from Roosevelt High School and the University of Washington as a Civil Engineer. He later received a Master’s degree from Harvard University. While at the UW, John entered the U.S. Public Health Service Commissioned Officer Corps and retired in 1984 after 27 years of service.

Capt. Bailey had a full life. He married Donna Maxwell in 1961 in Rockville, MD. He brought his engineering mindset to projects and problem solving and contributed his excellent copy writer/editor talents to many organizations. One of his proud accomplishments was mastering his new ‘smart’ cellphone when he was 75.

John’s love affair with boats began when he was 13 years old and living with his family in the Ravenna area of Seattle. His boats ranged from a 12’Penguin that he built in the garage to a 35’ Niagara sloop. In 1981, John & Donna started Baileywick Sailboat Charters on Chesapeake Bay that they continued until 2009 when they retired from their home in Lusby, MD and moved to Redmond, WA.

His work experience began at age 13 when he worked after school and weekends for Mr. Foster of Woodinville, WA, delivering sawdust for heating fuel to Seattle homes. His career in the US Public Health Service included an assignment to the US Park Service on the Natchez Trace Parkway, a master’s degree at Harvard, and 24 years (1960-1984) at the Center for Devices and Radiological Health in Rockville, MD, with a 2-year assignment to the State of Oregon Department of Health.

During the 1960’s in Maryland, John & Donna built their own precut solid cedar home which led to building several others as a part-time business and their intended retirement home in Lusby, MD. In addition to Baileywick Sailboat Charters, John & Donna owned Solomons Marine Towing, a marine assistance, towing, and salvage company on Chesapeake Bay from 1989 to 2002 and worked under Sea Tow and then TowBoatUS.

A memorial service will be held at Emerald Heights in Redmond, WA, on May 21 at 2:00pm.

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