James "Jim" Bailey

James H. Bailey (Jim, Beetle, Grandmaster B) died peacefully April 16, 2026 at his home in Crestview, FL after a 25 year battle with a brain tumor.  He was surrounded by the family he loved.

Jim was born Dec. 19, 1956 in Grand Rapids, MN to Rodman and Karin Bailey of Swatara.  He attended school in Swatara and Hill City, graduating from Hill City High School in 1974.

After graduation, he joined the US Air Force and completed Basic Training at Lackland AFB, TX.  His Air Force career spanned 21 years and he was stationed in South Dakota, Germany, Mississippi, Missouri, South Korea, North Dakota, Texas, England and Alaska.  His military service earned him the nickname “Beetle” of which he was very proud.

On Dec. 21, 1974 Jim married the love of his life, Gail Sawdey.  They raised 2 wonderful kids, Chris Bailey and Jennifer Blackwood.  He lived his life for his family.  He was very involved in sports and coached both kids sports teams when they were young.  He loved hunting, fishing, camping, bowling and cooking, but the biggest loves of his life were his grandchildren!  From the day of his tumor diagnosis in 2001, his life goals revolved around the grandchildren and their growth and accomplishments.  He was extremely proud of his kids and the grands!

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Jim was a lifetime member of VFW Post 9785 in Eagle River, AK.  He was also a member of American Legion Post 33 in Chugiak, AK, and a retired Teamster.

Jim is survived by his wife Gail and children Chris Bailey and Jennifer Blackwood all of Crestview, FL.  He is also survived by his beloved grandchildren,  Ariel (Cameron) Reyes, James Bailey, Hunter Blackwood, Bailey (Johnny) Maloney and baby on the way, Emma Wukasch, and Denali Thompson.  He also leaves 4 sisters,  Cheryl (Dennis) Graphenteen, Carla (Dale) Gillson, Ruth (Kile) Holm, Patty Bailey, and many nieces, nephews, brother-in-law Blaine (Patty) Sawdey, sister-in-law Gwen (Terry) Christensen, and many other family members that he loved very much.  He was preceded in death by his parents, grandparents, brother Dale, and nephews Terry and Tony Sawdey.

He will be greatly missed by his many, many friends all over the country.   We would like to thank all of those who called, sent messages, or came to visit.

The family invites you to honor Jim at a celebration of his life with full military honors on Sat. May 2, 2026 from noon to 4 pm at the Swatara Community Club in Swatara, MN.

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